How to Find Your Personal Style Again When It Stops Feeling Like You | Styled, Off Script Ep. 9

Figuring out how to find your personal style again can feel surprisingly disorienting—especially when the clothes and outfit formulas you once relied on no longer feel quite right.

In Episode 9 of Styled, Off Script, Annah joins Marge, Liz and Maloree to talk about exactly that moment. Annah started at Dia as a stylist and now works on the Style Leadership Team, which makes the tension especially relatable: she knows how to find possibility in someone else’s wardrobe, yet she can still stand in front of her own closet wondering, What feels like me now?

This isn’t a conversation about fixing a changing body or learning how someone “should” dress after 30. It’s about letting personal style evolve when you do.

When Your Old Style Formula Stops Working

For years, Annah had a formula.

Skinny or fitted pants. An oversized top. Comfortable, casual, a little edgy. It felt easy because she knew exactly how those ingredients worked together.

Then things changed.

Relaxed denim replaced the skinny jeans she was ready to leave behind. Her body changed too. But pairing the wider pants she liked with the oversized tops she still felt comfortable wearing didn’t give her that same pulled-together feeling.

Eventually she found the words for it:

“I just feel like I’ve lost my formula and I don’t know how to dress the body that I’m currently in.”

That distinction matters.

Sometimes you haven’t lost your taste. You still know what colors, moods, silhouettes or details appeal to you. The combination that once made those ingredients feel like you just needs an update.

Do You Actually Have to “Dress Your Age”?

Turning 30 becomes a jumping-off point for a much bigger question in the episode:

What does dressing your age actually mean?

There’s a strange expectation that adulthood arrives with everything figured out: your career, your identity, your relationships and apparently your wardrobe too.

The conversation pushes against that.

Liz talks about personal style requiring a certain amount of intentionality. Instead of waiting for your style identity to simply appear, there can be value in stopping and asking:

How do I want to show up in the world?

And Marge offers an equally important counterpoint: whatever answer you come up with doesn’t have to be permanent.

“You are not a tree. You can move.”

Your style can too.

Styling Other People Is Sometimes Easier Than Styling Yourself

One of the most interesting parts of Annah’s S.O.S. is that she knows style.

She began at Dia as a stylist and now works on the Style Leadership Team. Yet looking objectively at someone else’s closet is completely different from standing inside your own life, your own body and your own changing sense of self.

That’s part of what makes this episode feel so familiar.

Knowing what could work and knowing what feels like you are different questions.

Sometimes a second perspective—from a stylist, a friend or even someone whose outfits you admire—can help break the stalemate. Not because someone else gets to decide your style, but because they might see possibilities you’ve stopped noticing.

Maybe Finding Your Style Means Looking Back

Toward the end of the conversation, the group ends up somewhere unexpectedly useful: middle school.

Annah talks about rediscovering things she genuinely loved then—including the parts of herself she once decided were embarrassing or “cringe.”

Her takeaway?

“You gotta reconnect with your middle schooler.”

Not literally by recreating your eighth-grade wardrobe.

Think instead about the version of you who was beginning to develop strong opinions about what she liked.

What music were you obsessed with?
What colors caught your eye?
What outfits made you feel cool?
What subcultures, characters or people fascinated you?
What did you like before you got very good at editing yourself?

Liz points out that middle school is often when we first become hyperaware of style and identity. The opportunity now is to reconnect with that curiosity while leaving some of the self-consciousness behind.

This Week’s SOS: What Are the Shy Girlies Wearing to the Cool-Girl Party?

Then the episode takes everything out of theory and puts it into practice.

Annah has somewhere to go.

Her SOS: “What the heck are the shy girlies wearing to a cool-girl 29th birthday party?”

The invitation says “cute casual,” but Annah knows the birthday girl’s everyday style tends to be polished and flowy. Her sister—also attending—is fashionable and edgy. So Annah wants an outfit that feels appropriate for the room without feeling like she is wearing someone else’s clothes.

The conversation lands on a few directions.

Try the skirt you keep admiring

Annah had already mentioned loving long skirts on other people, especially styled with something slightly edgier.

That makes the party a perfect low-stakes opportunity to experiment.

A flowy skirt with a cropped or boxier tee changes the proportions without requiring a body-conscious top. Add combat boots and suddenly the look combines two things Annah already knows she likes: feminine movement and a little edge.

Play with proportions instead of changing your whole style

One of the recurring ideas is to make one directional change rather than trying to create an entirely trend-driven outfit.

If the skirt has volume, experiment with a shorter top.

If the top is oversized, try a shorter skirt or a different shape underneath.

The point is not to follow a formula someone else invented. It’s to play until you find the new formula that works for you. The brief framed the S.O.S. similarly: make Annah’s version of a going-out look feel current rather than dressing her like a “cool girl.”

That SOS inspired The Chill Girl Fall Box

Because the point isn’t to dress like somebody else’s version of the cool girl.

It’s to find the version that still feels like you.

Order The Chill Girl Fall Box

Personal Style Is Allowed to Change

Maybe the hardest part about feeling disconnected from your wardrobe is assuming there’s a version of your old style you’re supposed to recover.

But your style doesn’t need to move backward.

Keep the pieces that still feel right. Question the rules that no longer make sense. Try the skirt. Retire the skinny jeans if you want to. Borrow a little inspiration from your middle-school self.

Your style can change because you have.

That isn’t losing it.

That’s personal style doing exactly what personal style does.

Got a style dilemma?

We’re taking real SOS submissions for future episodes.

Whether you’re:

• packing for a trip
• stuck in a style rut
• navigating a wardrobe change
• or just not sure what to wear

Submit your own SOS request and we may feature it on the show!

Listen to the Conversation—or Read the Full Transcript

Below is the full transcript of Episode 9 of Styled, Off Script, featuring Annah and a conversation about changing bodies, changing tastes, the pressure to dress your age, finding a new outfit formula and one very real cool-girl-party SOS.

Click for Full Episode 9 Transcript.

Marge Welcome back to Styled, Off Script. We are on episode nine, which is—
Liz Goodness.
Marge Probably eight more than I thought we were going to do.
Liz What?
Marge I’m Marge. I’m one of the co-hosts here at SOS, and I’m joined by Liz, Maloree, and a guest, Annah. Welcome.
Liz Woo! Hi, Annah.
Annah Hi, nice to be here.
Marge This is actually a really fun episode because it started with a surprise SOS submission from Annah. The call was coming from inside the house. And as soon as I read through it, I was like, this is actually a really great episode topic to talk about. And Annah works at Dia & Co. and has worked at Dia & Co. for a long time. And so I will also celebrate her and applaud her for agreeing to be on this episode, as I know it was a little unsure there, but I think it’s gonna be a really great conversation, and it should feel like many of our other Teams work calls, but hopefully way more fun. And so excited to welcome you to the pod, Annah, and excited to get into your original SOS, followed by a topical SOS for an event coming up this next weekend that we’ll solve at the very end of this episode too. So would love to have an introduction, if you want to share a little bit about yourself, what brought you to Dia & Co., what you do at Dia & Co., and then we’ll get into it.
Annah Sure. Well, hi. I’m happy to be here. Although I am a little bit nervous, just because speaking is not what I would say is my best quality, but, you know, we gotta try new things.
Liz You’re a jack of all trades, a Jane of all trades.
Marge Truly.
Maloree Yeah.
Annah So let’s see. I started at Dia & Co. in, I think it was February of 2019, like seven, seven years ago. Is that right? And I heard about it through a friend who was a part-time stylist at the time. And I was just like, you know, this sounds like the perfect job. I had, like, just graduated college, like maybe a year before, and was still kind of trying to find my footing and where I kind of fit in in the workplace. And I was like, you know, this might be a good, like, temporary job, you know, so that, like, I can find my—
Marge Funny how that works out.
Annah Yeah. So I can find my full-time job. I don’t know. You know, I don’t know. And I ended up really just loving it. I liked that we work from home, and, like, I loved that aspect, but even more so I loved the people. I loved getting to be creative every day. I felt like I was kind of, like, putting together, like, a gift for each customer.
Liz Mm.
Annah And, like, I love giving gifts. It’s one of my favorite things to do.
Marge You really are a pro gift giver.
Maloree Mm-hmm.
Annah Well, thanks. I really—it’s like one of my, my—the ways I express my love towards the people that I care about. And I just was like, I was really excited to make these customers’ day. And yeah, and then eventually that turned into a full-time role. And then eventually that turned into, like, more of—it was called, like, the senior stylist role, which was more of, like, a—I don’t even know how to describe it.
Liz Yeah, it was cool. It’s more of like—
Annah Like an elevated stylist slash customer service role. And then that turned into, like, a labor planning data analysis role. And then that turned into, like, the role that I’m in now, which is—
Liz And—
Annah Operations management, where I kind of have a hand in a lot of different areas of our business. So yeah, it’s—
Liz Yeah. So—
Annah Just been, like, a really cool evolution, and if you had told me back in February—February of 2019 that I would still, still be here and be in this role, I would just be like, that is really random, but cool.
Marge Mm. We could do a live demo.
Maloree I laugh because I had, like, a very similar, like, roundabout way. Didn’t think I’d still be here, but here I am, like, way longer than I ever thought I would be, but, like, not in a position that makes any sense from where we started.
Annah Yeah.
Marge Hard same. Yeah.
Liz Maloree and Annah are great examples of people who just really have evolved at Dia & Co., started in one place, ended up somewhere completely different. And the skill sets that you guys have developed over the last billion years, as it seems, that you’ve been here, just are quite remarkable. I think it’s, like, a really fun reminder of, like, you never know where things are gonna take you and how.
Annah I’m just here for the ride.
Liz Exactly, exactly.
Marge I think it’s also, like, speaking to that, I think there’s a lot to be said around what people bring to the table. There’s a lot of things that you can train folks to do if they’re open to learning and have the, the right attitude to learn and grow and try new things and be sort of—get more comfortable being uncomfortable and not knowing how to do things, but have the attitude of, like, well, I’m gonna figure this out, and I’m gonna learn and grow and challenge myself and contribute to something that is meaningful and impactful. I think, like, it’s often called, like, soft skills versus hard skills, but I actually—
Liz Mm-hmm.
Marge Think that, like, the soft skills are the harder ones to teach or train someone how to do.
Liz Mm-hmm, mm-hmm.
Maloree Mm-hmm.
Marge And yet, as I look around our team, we are full of amazing people that are such, like, great partners that can tackle sort of any problem that gets thrown their way, and in a way that’s, like, very helpful and easy to work with. That’s not like—
Liz Mm-hmm.
Marge I’m above this, or I don’t know how to do this, and I’m not gonna try how to do—like, never once have we ever heard that in all the years that, that we’ve been around. And—
Liz What all the years and well?
Marge I think that’s sort of our, like, superpower, is we sort of learn how other teams work or learn how other businesses work. That is—
Liz Mm-hmm.
Marge Like a testament to, to the folks that, that do stick around and, and that have helped build this business from, from years ago. So—
Liz Well, I mean, one thing that I think is just very special about this team is no one ever says, like, that’s not my job or that’s not what I was hired to do. And because—
Maloree Mm-hmm.
Marge Yeah.
Liz If we did, we’d get nothing done. And—but I think it’s—
Maloree Mm-hmm.
Liz Like, to everyone’s benefit. And, like, the people on this—on this podcast, this podcast even is an example of, like, well, that’s not my job, but okay, if we didn’t do it, it wouldn’t happen. And we’ve each just, like, stepped into or created for ourselves roles that didn’t even exist before because we were willing to do things that weren’t, like, necessarily in our original job description. So, I don’t know, Maloree and Annah in particular, I think, stand out as people who have just really carved incredible paths for themselves because of their ability to sort of say yes or to not just stop when, like, something got in their way.
Marge Yeah, for sure. For sure. So I would love to get into, Annah, your original SOS, because I think it’ll help sort of lead to a couple of the other questions that we have asked other guests and sort of answered and asked ourselves. So I’m gonna get into it, and then we’ll sort of kick off where we think we can help guide you in this journey, and then I’m sure, hopefully, it’s things that other folks can contribute. So your original SOS was, quote, “I have completely lost my sense of style after turning 30 and also navigating fluctuations in my weight. What used to come more naturally to me when I was younger and straight sized has completely gone out the window with changes in my body and changes in what’s, quote, in style. I want to dress my age while also finding clothes that are of the times that I feel good in and feel like me. Any tips on how to feel excited about clothes again?”
Annah Yep.
Marge I love this. I love this so much.
Liz Mm-hmm.
Annah That’s basically it.
Marge I think what’s—I think what’s interesting about this, and something that I know I’ve gotten a lot, is, you work in fashion—
Liz Mm-hmm.
Marge Or you work in style. You obviously know—you must be so confident. You must know exactly what to wear for all of the things. Your style is so trend-forward. Like, all of these things. And I’m like, what? That’s crazy.
Liz Mm-hmm.
Marge No. And so—
Annah Well, I think it’s—it’s, like, also different when you’re styling other people versus yourself. Like, like, for some reason—
Liz Mm-hmm.
Marge Absolutely.
Maloree A hundred percent.
Annah I feel like I have a blind spot when it comes to what I look good in and—and what I look—I don’t know. I feel like maybe there’s some, like, sort of dysmorphia or something where—
Liz Yeah.
Annah I just don’t know what I—what looks good on me, but I know what looks good on other people. So, yeah, it’s just—it doesn’t come as easily.
Maloree A hundred percent.
Marge Working with you for as long as we have, knowing how, like, very logically you approach problem solving and things, I a thousand percent understand how well you were at styling, because you approached it very, like, logically. Like, I’m taking in all the information that I’m given, I’m using it and applying it to what I have available, and sort of problem solving for that individual customer, pulling yourself out of it. And I think it’s very normal for folks to sort of not know, as life evolves and changes, what style works or what you like, or sort of have that blind spot. And I’m curious to hear what, like, Liz and Maloree—like, I feel like we’ve talked about this in the past, where, like, you both have had, like, shared experiences or similar to Annah. Like, any suggestions or, like, ways to sort of approach this from the top before we get into how you view your style from before and now and—and all that?
Maloree I just—when we first were talking about Annah’s SOS, I just remember being, like, a hundred percent same, because I am, I think, just a few months younger than Annah, but, like—
Annah Yeah.
Maloree I don’t know what it is about—it’s like 30 is so pivotal, I guess, in a way. Like, I don’t know. As a kid, I thought by 30, like, I would have my entire life figured out. Like, this would be—like, I would be a true adult. And then I turned 30 and I’m like, shit. I actually don’t know what I’m doing. I still feel like a kid, and I don’t have it together like I thought I would. And that has just, like, turned into also, like, okay, looking at it as, I am an adult. I am the adult in the room, and I want to present myself that way, but also how do I do that? Like, I don’t—
Annah Mm.
Maloree Want to dress like I did when I was 21 because I’m not that person anymore. But also, who do I want to be? Like, how do I want to present myself? And that has been very—I have been struggling with the exact same thing, because it’s like, my body has changed. I don’t know how to dress myself. I literally went to something over the weekend, and I sent, like, four different outfits to my mom and my sisters, and I was like, I don’t know how to dress myself. Like, I can dress other people, but I was like, I need help because I don’t know how to dress myself right now. And—but it was just, like, the exact same. I don’t know what it is. It’s that time in your life where it’s like, I actually am an adult, and I want to look like one, but also how?
Annah Yeah.
Liz Well, I’ll just, as the older lady in the room—
Marge Ha ha.
Liz At the ripe old age of 45—46? 45? I forget. Like, yes. And, like, I would just say, while this was 15 years ago for me, I think, it is, like, a very strange time to be getting dressed. Like, there are just so many things, I think, that have changed. And at least for me—I will only speak for myself—like, while I was quote-unquote an adult, there were so many transitions going on in my life when I was turning 30, around 30, that it was probably one of the times that I had the most questions about who I actually was and what my identity was. Like, things in my life were moving so quickly that I had very little time to focus on, like, what was core to me and how I wanted to show up in the world. And I think there were just, like, a lot of outside influences. I personally was a new mom. I had moved to a new place. I was figuring out my career still. And, I mean, I guess I’m still figuring out my career, but I was figuring out my career and, like, the last—I—I just—there were so many moving parts in my life that it felt like every day I was showing up different. And I couldn’t really—I didn’t have the bandwidth or—or, I don’t know, the understanding of, like, that part of establishing myself and who I was as a mom, as a partner, as someone in the workforce, was, like, also having—I’m gonna use, like, a brand identity—of who Liz was. And that was something that, like, for me came, like, a little bit later, actually quite a lot later. And I had a lot—I had to rely on people around me a lot more at 30 to sort of figure out my style.
Marge I think that’s—I think that’s spot on. I—I remember feeling like before I hit 30, I thought by 30 I, again, similar to Annah, like, everything would just sort of click into place and I would just, like, know all of the things and, like, somehow things would magically make sense. And I—I blame maybe TV for—
Maloree Mm-hmm.
Marge Building this, like, idea of what being an adult was.
Liz Totally.
Marge And—and, like, feeling like I had to have it all figured out, and—and that by 30 everybody else knew what they were doing and whatever. And I remember having a conversation with my mom, who was 43 when I was born, and had—had sort of said, like—I think at the time she was maybe in her mid-70s. Now she’s 80. She was like, “Just so you know, I don’t know what I’m doing. I’m just trying.” And I think that opened up something in me that was like, okay, I don’t have to have it all figured out. I just have to—
Liz Mm.
Marge Try. And sometimes it’s trying my best, and sometimes it’s just trying. And figuring it out along the way, and sort of taking the pressure off myself to try to feel like I had it all figured out in—in all aspects of life, but also realizing that by comparing myself, or comparing myself to the version of other people I thought existed, wasn’t helpful.
Liz Mm-hmm.
Maloree Yeah.
Marge And made me, like, get way in my head. And then I sort of said, you know what? What if I just did, like, what I want? What if I prioritize, like, what I want in—in as many aspects as I can in my life? Obviously, there’s so much of life that you can’t prioritize yourself for. But how do I sort of take some of that pressure off myself and add in some more things of what I like to do? And I think it’s, like, an ongoing, like, practice all day, every day, but it was sort of eye-opening. Now that I’m 38—or no, 38? No.
Liz Yeah.
Marge I will be 38.
Annah Huh.
Marge After a certain year, you’re just like, what?
Annah Yeah.
Marge But now that I’m 38, I’m like, okay, this makes sense to me. I do—I wear what I want to wear. Sometimes it’s got some, like, suggestions from others or inspired by other people, but I can sort of take that pressure off myself and focus on other things. So I do think, like, with age comes wisdom and experience and just sort of taking—like, learning to take the pressure off of yourself. But in the meantime, I think it’s also really fun and exciting to work for a company where—and work with friends and people that have similar experiences to you and have either the experience, like Liz or me or Maloree, and sort of be like, you too? Okay, cool. And then we come together and say, well, this is what I like and this is what you like and sort of find—find ways to, like, bounce ideas off of each other and—and sort of help—help throughout the process.
Liz I think—I feel like you said something—something that you said, Marge, made me think about the intentionality that has to be there to define your own personal style at some point. Like, I think I just assumed one day I would wake up and be like, this is what I wear now, and, like, this is who I am. But, like—like, I—
Marge Yeah. Sweater sets forever.
Maloree Mm-hmm.
Liz Right. But, like, I guess—
Maloree Yeah.
Liz And I definitely thought I’d be wearing sweater sets, but—
Maloree Ha ha.
Liz I—I guess, like, at some point it did dawn on me that, like—I mean, I don’t think it was—there was a deep awareness, but I think that there’s a moment where you have to say, as you are continuing to grow and define yourself, part of that is your style too. And so just as much as you’re like, these are the values that I have in my life, these are the—you know, this is the way I want to live my life, and those things are intentional, this is the way I want to present myself to the world in a style sense sort of has to be intentional too, if that matters to you. And—and I think, yeah, like, you just have to take the time, like Marge was saying, to invest in yourself in that way. No one else can do that for you, although it’s good to have friends to support you.
Maloree Yeah.
Liz I think—I think you sort of pausing and saying, how do I wanna show up in the world? How do I wanna present myself to the world? Is—is a real part of it.
Marge Also knowing that—
Liz Okay.
Marge You can always change.
Liz Of course.
Maloree Yeah.
Annah Yeah.
Marge One of the best quotes I remember my therapist saying years ago was, “You are not a tree. You can move.”
Liz Oh my God. That’s great.
Marge I know. You can also move trees if needed, but, like, you don’t have to live where you’re planted today. And your style can evolve and grow and change over time. I think that’s the coolest part about what we do, is being able to see that evolution. And sometimes you go back to things that you loved before that feel like a version of you before. Other times you’re like, I’m never gonna wear that again. And—
Annah Mm-hmm.
Marge You get to dictate what that looks like. I would love to know if we could—Mal, are you gonna jump in? Okay.
Maloree Nope.
Marge I would love to jump in and ask just a couple questions to get to know you a little bit more, Annah, and your style. So you talk about now sort of struggling with not knowing what—what feels like you or what feels like your style. Can you share a little bit more about how you would describe your style in, like, your early to mid-20s versus now? Or are there certain pieces you really love, certain silhouettes, certain colors, patterns, anything that you wouldn’t wear now that you loved—
Annah Yeah.
Marge Then?
Annah Yeah. So I would say, like, in my teens and early 20s, I kind of had, like, a formula, like, down. Like, I—I guess I—it would be, like, sort of like a uniform or something. But I was big into skinny jeans, big into the skinny pants, but also loved, like, an oversized sweater, an oversized shirt. And I felt—and—
Liz Mm.
Annah I felt like it, like, even though the shirt—the top—was oversized, I still felt like I looked put together with the more fitted pant. And yeah, I—that was kind of my formula. And also my, my body type was more of, like, just a stick. So I—I just, like, I—I, yeah, I just, like, I knew what looked good on me. I knew what felt comfortable. And I would say that my style has always been, like, comfortable, casual, with, like, a little hint of edginess every now and then.
Marge Yeah.
Annah And also, like, I guess sometimes it—I guess it would be kind of like a gender-neutral style with, like, a surprise, like, hint of feminine in there every now and then. And—and that hasn’t changed. I still like those things. But now that, like, parts of my original formula have gone out of style with this—with the skinny jeans, which I—I will say I did fully embrace the more relaxed jean when that started coming into style. I loved that. And I would instead wear, like, a relaxed jean with a fitted top. But then, as I got older and started gaining weight, I didn’t like how the fitted top looked on me anymore. But I also, like—so I would start wearing more oversized tops and the, like, wider pant, but then it didn’t look—it kind of looked frumpy. I don’t know if that’s the word, but I didn’t feel put together anymore. And, yeah, sorry, I—I—I kind of feel like I was a little all over the place there, but—
Marge No, that’s—that’s spot on.
Annah But yeah, I just—I feel like I’ve lost my formula, and I don’t know how to dress the body that I’m currently in. I’m also somebody who, like, I—I don’t like showing off my body, and that’s—and it was really easy for me to kind of hide it when I was more of, like, a straight size, very skinny. Just wear oversized things and you can still look put together somehow. But now when I wear oversized things, it just feels like I didn’t put any effort in or, like, I’m trying to—I, like, it gives off insecure, but it’s hard for me to articulate. I just—I’ve never liked people having any sort of opinion about my body, so I just like to kind of, like, hide it. That’s what makes me feel most comfortable and confident. I—I just don’t want people to perceive me in that way, if that makes any sense.
Marge Hard same. Yeah.
Annah But it’s not, like, an insecurity thing. It’s just, like, that’s just how I want to present myself in the world, is, like, I don’t want people to have any sort of opinions on my body at all. Why can’t I just be a floating head?
Liz Mm-hmm. You’re too cute to be a floating head.
Annah But does—but does that make any sense? I feel like I’m not articulating it as well as I want to, but, yeah. That—I—that’s kind of where I’m coming from.
Marge That makes total sense.
Maloree It makes total sense to me.
Liz It makes total sense to me too. And I think it’s so—I—this sort of—I think speaks to what I was saying before. There are so many contributing factors, like, happening at once, whether it be the state of style in the outside world, like, how you’re feeling about your body, how your body is changing. Like, all of those things are just distractions. They, to me at least, those things get in the way of, like, sort of figuring out who—what your style is and who you are, because to—at least to me, like, those things are really just noise. Like, what’s most important is what you want to put out there and, like, what makes you feel like you and what makes you feel comfortable. And that doesn’t mean that, like, changing trends aren’t important and, like, the way, you know, your body is changing isn’t important, but those are secondary, I think, to, like, what you want to put out.
Annah Yeah.
Marge Speaking of—of trends, are there any trends or styles that you love on other people but can’t quite figure out yourself, or feel maybe you’re curious to try?
Annah Yeah, I love—I love that, like, skirts are—seem to be, like, back in a big way, like long skirts.
Marge Yeah.
Annah Especially when paired with something, like, an edgier top or, like, an edgy combat boot. I like—it kind of, like, it speaks to that style that I like where, like, it’s edgy with a feminine flair. But I just have—and I—I even felt this way in high school too, where I would try on skirts and I’d be like, something just doesn’t—it doesn’t look the way that I want it to, and I don’t know why. It might just be my proportions, but whenever I wear a skirt, it just—I feel like it doesn’t look right on me.
Liz Yeah.
Annah I—it maybe it’s just—I have, like, a smaller torso, longer legs. I don’t—I can’t figure it out. Maybe it’s just a—a me problem and it does look great. But every time I’ve tried on a skirt, I’m like, this doesn’t look like how I was picturing the look to be.
Marge I think skirts are a—I think that’s super common. I think skirts are something that a lot of folks struggle with. I know from my years of styling, skirts were always really difficult for folks to figure out how to put the outfit formula together. And I think a lot of it has to do with where you typically would sit a pair of pants on your waist, or, like, where you feel comfortable. Sometimes a skirt either needs to go higher or lower, depending on how you’re gonna style it and how it fits you best and the shape of the skirt. I find I typically wear a skirt a bit higher up on my waist, like, to the very top of my hips, versus sometimes jeans rest a little bit lower.
Annah Okay.
Marge And it’s just from playing with it and looking in the mirror, and then seeing what other folks are wearing and, like, seeing what fits—fits best. And then it also has to do with, like, the length of the skirt and where it—where you want it to fall for what shoes you’re gonna wear or what top you’re gonna wear, that sort of thing. But it—it is a very—I would think it’s a very common difficult item to style, based on my experience.
Maloree Mm-hmm.
Marge But I love that trend.
Liz So I think skirts—like, first of all, I love the look that you’re describing. And I have a follow-up question that I want to come back to. But skirts, I completely agree with Marge. I think skirts are hard because they require so many different pieces to go with them, and—and those other pieces are sort of dependent on the skirt that you’re starting with, like, whatever your starting point is. But one tip I have for a skirt is to start with a skirt with a knit fabrication when trying to figure out, like, the silhouette and length that works for you. I know that, like, knit might not be, again, the most, like, trend-forward, and I think we’re really lucky right now that there are so many different fabrications that have, like, a—a knit component to it. So whether it’s rayon with a stretch or something that has a little bit of spandex in it to—to just give it some give, I would lean towards knit rather than woven, just because that fabrication is so much more, like, fit-wise, forgiving and easy to work with. And that can help you, like, at least establish what kind of silhouette and what kind of length work best for you. And then you can sort of begin to play with different fabrications, maybe more in the styles that you’re looking for. But that’s my tip.
Annah That’s a great, great tip. I hadn’t thought about. And then, like, if you’re into sewing, I feel like knitted fabrics are easier to hem if you need to.
Liz There you go. So you can even play around with the length if you have to. But whether it be, like, a midi skirt, a maxi skirt, even a mini skirt, pleated, unpleated, like, I would really recommend starting with knits and then going into wovens after that.
Annah Okay. I like that.
Liz Can I ask my follow-up question? Do you have—
Annah Yes.
Liz Like, a celebrity or two whose style you, like, sort of jive with?
Annah Sort of. I only—in the—so I—I was, like, really into color analysis a couple years ago, and I had, like, my color analysis done, and turns out they don’t go by what your favorite colors are, which was a real bummer for me.
Marge Yeah.
Annah So I found out that I’m a dark winter, which is, like, dark, moody, like vampire colors, which it does kind of work with, like, my edgy vibe. But I—I really love darker earthy tones, and that’s just—apparently those aren’t my, my best colors. But, you know, I—I feel like everybody looks best in whatever they feel confident in, so I don’t—it’s like you take it with a grain of salt.
Liz I agree.
Annah But anyway, all that’s to say is apparently Anne Hathaway matches my color season, and I really—
Maloree I could see that.
Annah I really do love a lot of her looks.
Liz Mm-hmm.
Annah I wouldn’t say that my style matches hers at all, because she wears a lot more elevated, elegant clothes than I do. But I definitely—I look at whatever she’s wearing and I take, like, mental notes of, like, okay, that’s a good color for me. All right.
Liz Interesting. I could definitely see that.
Marge That’s so topical because she’s on the red carpet for some Netflix show that she’s in. She’s, like, all over everywhere. And having a baby. She’s gorgeous.
Maloree She’s, like, everywhere right now.
Annah Yeah.
Liz She’s everywhere.
Marge But she had this amazing—and people, of course, are having big feelings about it because heaven forbid a woman pregnant, like, wants to look trendy and cool. Ugh. She looks incredible. And she has this really cool, like, low-rise, like, wide-leg denim with this high-low hem, like, baby blue top that is sleeveless but has, like, a really, really long hem. But underneath it is, like, red, so it kind of gives, like, the Louboutin, like, peek of, like, red bottom somewhere. It’s gorgeous.
Annah Cool.
Marge And I—as soon as you said Anne Hathaway, I can totally see you in, like, a light—like, light baby blue—
Annah Mm-hmm.
Marge That would look really, really nice with your, like, dark hair and—and features and glasses. That I—I think would be really cool. Like, it was just a really cool outfit that could be styled a lot of different ways.
Liz The other thing that Anne Hathaway does a lot, which I think maybe speaks a little bit to your, like, androgynous—you were talking a little bit about, like—
Annah Mm-hmm.
Liz Yeah, androgynous look—is she does a lot of menswear, or she’ll, like—
Marge Yep.
Annah Yeah, yeah.
Liz Add a piece that’s more menswear-inspired. So, you know, listen, I understand that you’re—that you’ve moved out of skinny jeans, but I think also if skinny jeans work for somebody and that’s part of, like, quote-unquote your uniform and you feel good in it, they look good. Skinny jeans are never gonna go away completely. But, like, to add—
Annah Well, let me just say, I’m—I’ve moved past the skinny jeans. I—I understand if it works for other people. I’ve—I’ve—
Liz Right.
Annah I’ve retired those. I’ve retired—
Liz I love that for you. But I love that for you. So, but like—
Annah I’m never going back until they come back in style.
Liz To add, like, the jeans, whatever style they are, and add, you know, a piece of menswear with them, whether it be a blazer or a bomber jacket or something that—or, like, an Oxford work shirt that has, like, a little bit more structure to it. I think—
Annah Mm-hmm.
Liz That those—that sort of gives me, like, an Anne Hathaway style as well, but also screams Annah.
Annah I like that.
Marge Is there an outfit that you’ve worn recently that you really loved or really felt like yourself in that may help us with the—the formula for the Annah formula?
Annah The only thing I could think of is there—a couple of years ago, we had—it was actually an 11 Honoré sweater that I got when it was, like, on super sale. It was, like, this really pretty cobalt blue, like this just vibrant blue. And I tried it on, and it looks so—it looks so good on me. It makes me look like I’m just glowing from within. And it fit me so great, and I wore it with, like—I paired it with, like, black cargo pants, and it—it was, like—so the cargo pants were more of, like, the looser fit, and then this sweater was, like, a cropped, fitted sweater. And then I just wore sneakers with it, and it was, like, I felt so good in that outfit. And I was also kind of, like, on a fitness journey, so, like, I was feeling strong and good. And yeah. And I mean, I would still—I would still wear it. I don’t know if it would—if it fits me super great right now, but I loved that outfit.
Marge I love the—the bright blue color. I think that’s one color that looks—I think there are some colors that look great on everybody. And that, like—
Annah Mm-hmm.
Marge Bright, bright royal blue typically looks—
Liz Mm-hmm.
Marge Good—
Annah Yeah.
Marge On everybody.
Annah Totally agree.
Liz And Annah, I love hearing from you in particular, like, the impact that color can have on how you feel in an outfit, because, you know, I just—I—I, some—I don’t know. Like, when I—most of the time I only see you from the waist up.
Annah Yes.
Maloree Ha ha ha.
Liz And, like, you—you do wear a lot of, like you were saying, earth tones and—and more muted colors. And so to know that, like, brighter colors aren’t out of the equation, I think is great and, like, something that could definite—I could definitely see that becoming part of your work—or not work uniform—but, like, your sort of standard package of what you wear.
Annah Yeah. And I—I’m not afraid of color. I think I just get in this rut where I’m just like, I don’t know. I just wear whatever’s clean, and I just throw it on.
Maloree Ha ha ha.
Marge Also very relatable.
Liz Better than not clean.
Maloree Same.
Marge Very relatable.
Annah Yeah.
Marge Very relatable. Okay, I would love—because it—we sort of teased this when you talked about your ideal trend or style that you’re looking for. So I think this would help lean into the SOS that you shared for an upcoming event, and I think we can give you some options there. And some—some tips and tricks before we—we round this out. So you had sent me a Teams message that said, “Urgent. I have an upcoming—” Maybe it didn’t say urgent. I cut out that part, but I’m gonna take it as urgent.
Maloree Ha ha.
Marge You’re like, “Oh my gosh, I have an urgent SOS. What the heck are shy girls wearing to a cool girl 29th birthday party?” I was just invited to one over the weekend, and you said it’s this upcoming weekend, not the one that just passed, but upcoming. And you needed some advice. So I took it to the chat, and we brainstormed a couple ideas that I think we should talk through here. And funny enough, it sort of ties into the—the skirt, the skirt option. The one bit of feedback I will give on skirts—and I think this is something that, like, some people need to be, like, held their hand with a little bit—is that, try—if you have never tucked in a shirt before, that’s okay.
Liz Yeah.
Marge You don’t have to. But with a skirt, try it. You can—
Annah Mm-hmm.
Marge Wear a shirt over a skirt, and that could be okay. But even, like, a little front tuck or, like, a tuck-in that, like, defines your waist a little bit—not if it even falls to your waist or whatever—but just the, like, volume on volume—
Liz Mm.
Marge Or the, like, playing with different shapes is part of the fun of wearing a skirt. And there are a lot of really, like, fun ways to wear a skirt with, like, a casual band tee that you can tuck it in and feel really flirty and feminine. And you wouldn’t necessarily tuck—you may not in your everyday life tuck in a shirt into your jeans. But somehow, because the skirt is a little flowy, it may sort of give you more comfort in—in areas where, in jeans, you would typically want, like, a shirt to cover it—
Liz Right.
Marge You have—
Annah Mm-hmm.
Marge The skirt there to do that. And if you’re—last caveat there with, like, finding the silhouettes for skirts: if you own a dress that you like the skirt to, or the shape of the skirt, you could just toss a tee or something on top of it and make that your skirt, or use that to help play with—with other options before you invest in—
Maloree Uh-huh.
Liz Mm-hmm.
Marge In a skirt that—that you’re not sure what it—what you—you like yet.
Liz Yeah.
Annah Great tips.
Liz Absolutely agree.
Marge So what are shy girls wearing—I can’t say “shy girls”—
Annah Yeah.
Marge Wearing to a cool girl 29th birthday party?
Annah I will say, to give some more context—
Liz Yes, please.
Annah This—the girl who is having the party, she put the dress code as, like, cute casual. But I also know how she dresses on a daily basis, and it’s—
Liz Okay, tell us that.
Annah It’s, like, she’s wearing very, like, flowy dresses, flowy skirts, just always looking put together. So I know that it’s, like, probably a little bit more elevated than my idea of what cute and casual is, just based on—on what she wears. And I’m also—my, my sister is my plus one. And my sister is also, like, very fashion-forward, very edgy, very cool. And I just—I want to make sure that I’m, like, I’m fitting the vibe of everybody.
Liz Love it. Okay, I have some thoughts.
Annah Okay. Give it.
Liz So I—I definitely want to try a skirt. Like, I think that you should be trying a skirt for sure. And like I said before, I would, if possible, go with something knit just because I think that you have more flexibility. I’m picturing, just the way you’re describing, with combat boots, I’m picturing one of two skirt options. One would be, like, a true maxi skirt. So something that, you know, doesn’t show your ankles, but also, like, doesn’t—so that you’re not gonna trip over and sweep the floor. But if you’re wearing combat—if you want to wear combat boots, I would go with a true maxi. I think it would be super fun to try something with some color in the skirt. So, you know, we have—I always go back to our assortment—we have a number of different options right now that are a little bit more of the earthy tones that you tend—that you like. But I think what’s nice, they’re, like, earthy tones with a punch. So in particular, we have something right now that has sort of a rust red in it that I think would be, like, really, really nice. It has some stretch to it. What I like about it in particular is that—a skirt that has, like, a flat or firm finished—I, why can’t I think of what the word is?—waistband in the front, but in the back is elasticized.
Annah Yeah.
Liz So again, like, I just think that that gives, like, a little bit more versatility with fit. You can wear it high up, like high-rise jeans, right under your breasts, which is where I tend to wear my skirts. You can—
Maloree Ha ha ha.
Liz Also pull it down and, you know, wear it as low-rise, like a little bit more low-rise, if that’s the look you’re going for. But for me, I would wear it pretty high above my belly button. And then instead of doing a front tuck—although I love a front tuck—but if I’m gonna wear it that high, I would wear it with a cropped tee, sort of a boxier-fit cropped tee. I—I know you’re going for a little bit more, like, casual elegance, I guess is what I would say. So in this case, I probably wouldn’t do a graphic tee. I would do, like, a solid or burnout, some—some sort of tee that has a little bit of extra to it, maybe even something with, like, a—like eyelet detail at the top or something, but something that, again, flows away from your body. So something cropped but not oversized. Or, yeah, cropped, flows away from your body, but not oversized. And if you want to do something sleeveless, that could work too, depending on the weather. And then your combat boots, because why not? And I think that we’ve talked about this before, but if you’re wearing the right pair of boots, you can take over the world, and it really doesn’t matter what else you’re wearing. So that—that’s one look that I would recommend for this get-together. I think, like, you’ve got the flowy going, you’ve got the color and the, like, sort of earth tones going, and then you’ve got the combat boots to really bring a little bit more edge to the look. And, like, a chunky necklace or a drop necklace or something, just to add a little bit of interest on top, is what—is one look that I would recommend.
Annah How do you, like, imagine the hair for that? Is that a hair-down?
Liz Ooh. I mean, for you, long and curly and, you know, put those rope braids in and then take them out. They’re, like, perfect. I would wear your hair down. That, if that’s my—that’s the question, yeah.
Annah Okay, cool. That’s all—that’s also a problem I always have, is, like, what kind of hair is this outfit supposed to have?
Liz I love that question.
Marge I’ve been on a—a hair, a hairdo journey recently and have found so many cute ideas on Instagram of people doing, like, easy, easy hairstyles in, like, under five or ten minutes. And very fun. I also picture this, like, if you leave your hair down but you want your hair out of your face, like, middle or side part, two little braids pulled back, like, in the front, to, like, pull sort of the front of your hair back, like connected in the back. Just so that—I am someone that, if I don’t pull my hair back out of my face, I will be playing with it or it’ll be behind my ears forever. So—and it’s also hot—so I like to sort of take some of it off the—off the top.
Liz Can I just also say, and Annah, I don’t know if you would ever do this, but I can also picture this look with, like, a short skirt too, like an above-the-knee skater skirt.
Marge Yeah.
Annah Mm-hmm.
Liz I’m not at all talking about a mini skirt, but something, especially if you’re doing combat boots, something that, like, maybe has, like, a lace detail at the bottom. And then you can wear that, like, longer oversized band tee with it if you want, or something.
Annah That’s cool.
Liz You know, I love a button-down. Marge is always talking the button-downs. Then with the front tuck with the shorter skirt, that’s where I think you can play, like, with proportions a little bit more. So, like, if you’re going with the long skirt, I would do the crop tee. If you’re going with the short skirt, I would go with something a little bit more oversized. Even with—I mean, I know it’s not the weather, so I don’t even know why I’m saying this—but, like, a short skirt with a blazer, back to that sort of menswear—
Marge Yeah.
Liz Play on things, I think, could be really, really cute.
Marge And depending on the heat, and if you don’t want to break out combat boots or boots yet, swap in sandals and you’re good to go. And, like—
Liz Mm-hmm. Mm-hmm.
Marge Kind of any sandal at this point.
Liz Mm-hmm.
Annah Ideas. I like it.
Marge Any—Suggestions, Maloree, based on your style ideas?
Liz Usually don’t worry.
Maloree Yeah, I was gonna—my, my vision is very similar to Liz, but we have a red floral maxi skirt right now. I think it’s from—I think it’s East Adeline.
Liz Mm-hmm. Mm-hmm.
Maloree But I think—I mean, we’re talking about colors—
Liz Yeah.
Maloree We’re talking about Anne Hathaway and how you said that you like edgy, but you like to also throw in, like, a little feminine nod, and this skirt has, like, very dainty floral on it, which I—
Marge Yeah.
Maloree Think will be really cute with the edgier—like, like I was picturing a band tee, like cropping a band tee. I am personally—I don’t like a crop tee on myself, but with a skirt—
Liz Yeah.
Maloree Pulled up right under my boobs, I—
Liz No.
Maloree Need a crop tee. Like, that’s—that’s the only way that I think, for my body type and the way that I like to wear skirts, that it looks good. And I think that it looks good on everyone when it—when that happens. Because, like Marge said, like, you have—you’re playing with so many different shapes, and with the skirt already being flowy, crop tees just look so good with a maxi skirt, in my opinion. But I think, like, an edgier band tee, or even if it’s a plain, just burnout tee, would be cute. And with that skirt and the combat boots, I think it’s just, like, a perfect combination of the edginess with the colors and the feminine, like, little feminine nod to it. And in terms of hair, I like to do a half-up with a claw clip so that I have the option, if I do get really hot, I can just throw—
Liz Yeah.
Maloree All of my hair up in that claw clip and not have to have, like, a—a ponytail holder somewhere else or something, like, extra. It’s already in my hair, so I just throw it up. But I like to do a claw clip, and it’s like a little, like, bun. Like, you kind of do a bun with it so it sticks out the top, and then you have a cute—a cute claw clip. Like, you could do something fun with it. I know there’s, like, so many cute ones now. I saw one the other day that was, like, a wiener dog, and it was so cute. But just doing something fun like that too that adds a little bit of interest and a little bit of personality would be fun.
Liz Mm-hmm. Mm-hmm.
Annah I like that. I have so many good ideas now. Like, I’ll have to send you guys a picture on the day of—
Maloree Yes, yes.
Marge Yes, please.
Liz Can I just—
Marge Yes.
Liz Give, like, one other option if you don’t want to go the skirt route? Like, I think that we—I—
Annah What year?
Liz I—I’m not sure how much we’ve talked about the love of the wide-leg flowy pant, especially this time of year. But, like—
Annah Yes.
Liz Especially if you’ve evolved out of skinny jeans, you’re more familiar with different silhouettes. Like, I think a wide-leg pant made out of a lightweight material is a great alternative to sh—to shorts. No, to skirts too. It sort of gives—that you were talking before about how your friend wears lots of flowy materials. It can sort of be an accessible way to enter into that sort of style without making a hard left and being, like, super romantic and girly. And again, I think it’s about playing with proportions, but I do think there’s sort of two ways to go. I know before you were talking about sometimes you feel like if you wear oversized and oversized, it can feel frumpy. But I do think that there’s a way to do oversized and oversized in, like, a non-frumpy manner. Maybe it’s a more tailored oversized top, like that Oxford work shirt with, like, a strong collar, or you can go the other way, which is to wear something more fitted on top, like you were talking about before. And I think, like, a muscle tee would be really, really—
Maloree Mm-hmm.
Liz Cute with a pair of wide-leg pants.
Annah Okay.
Marge Yeah, that—that—
Annah I like—
Marge Would be my, my suggestion. I love a good wide-leg pant, especially in the—
Liz Hmm.
Marge Summer.
Liz Yeah.
Marge It’s so flowy, and I’m really loving the muscle tee options these days.
Annah Wide-leg linen.
Marge Ooh, baby.
Liz Yeah.
Maloree Yes.
Liz That would be fantastic. Or, like, even as Maloree was saying, with the maxi skirt having some pattern, like, a wide-leg pant is a fun way—and I’m not saying it’s right for this occasion necessarily—but it’s, like, a great way to bring in some, like, bold pattern too that you might not, like, want to wear up against your face, but that can be incorporated with the pants.
Annah Sorry, Marge, I didn’t—I didn’t mean to interrupt you.
Liz Please.
Marge No, not at all. I think—I think these are great options. I—I wonder, let’s see. I wonder if there’s—are there any other comments around dressing—
Liz Yeah, other—
Marge Or sort of who you are today versus who you were then? Any wisdom you would like from the group or anything else sort of you wanna touch on? I can cut this part out if we need to, but—
Annah Let me see. Any wisdom. I guess maybe this is more for—for Liz and Marge, since you guys have—have kind of been where I—me and Maloree are. What kind of got you back into feeling like, like, I really like that, that looks great, like, to finding your style again?
Liz That’s a great question.
Annah I feel like I’m sort of getting that back. And I think that just is kind of, like, the nature of being early 30s, is, like, you’re—you, like, lose yourself there for a little bit, but then you find yourself again. And for me, I’m, like, really starting—I’m, like, finding my middle school self again for some reason. I don’t—
Marge Yes.
Annah Know. I don’t know if that’s, like, a normal 30-year-old thing, but, like, everything that—like, in my early 20s or even teens, where I pushed away everything that I was in middle school, when I—I feel like middle school is who you truly are. And—
Liz Mm-hmm.
Annah I’d be like, no, that’s so cringe. I ne—I never liked Twilight. What? People like Twilight?
Maloree Okay.
Annah And now I’m just, like, fully back into—like, I’m, like, fully back into my middle school mode and re-re-getting reacquainted with her, and realizing that all the things that I thought were cringe are actually cool and who I am, and embracing the cringe, I—
Liz Damn straight.
Annah Guess.
Maloree My midnight Twilight premieres as a badge of honor now, because I was there.
Liz Oh my God. Amazing.
Marge Guys, I used—
Annah I was at the Twilight premiere too, as well.
Liz Oh my God, stop.
Marge I used to watch Twilight every night, bootleg, on my computer to fall asleep for, like, months.
Liz I gotta look at both of you.
Annah I have, like—it’s a core memory. That was the—the Twilight premiere, midnight premiere, the first one. That was the best movie theater experience I have ever had in my life.
Maloree Mm-hmm.
Annah If we—
Marge Wow.
Annah Can just go on a quick tangent.
Liz Always, always.
Marge Always. Yep, always.
Annah So I had been, like, obsessed with the books in middle school. And then I forget when the first one came out. I feel like I was in eighth grade when the movie came out. But I just remember that movie theater being completely filled with every girl from my middle school. And when Robert Pattinson came on the screen for the first time, it was just utter chaos, screaming. It was like he was—like, it was like Beatlemania or something.
Marge Oh my God.
Annah And I thought—
Liz It’s amazing.
Annah This was, like, the best movie I had ever seen. I went and saw it twice. And—
Maloree And now you—
Liz I mean, what do you mean thought? It is.
Maloree Watch it, and it’s like, what the hell was this?
Annah But now I—I love it in a different way because I’m kind of just, like, laughing at who I used to be and just how ridiculous—
Maloree Mm-hmm.
Annah That was. But I—yeah, but there was a time when that—that—that part of me, I pushed it away and I was like, that’s so embarrassing, that’s so cringe that I was into that kind of thing. And now I’m—I’m fully embracing it again, and that’s where you find joy. You gotta—you gotta reconnect with your middle schooler.
Liz There you go. Well—
Marge Yep.
Liz I think that you are saying it perfectly. You gotta re—you gotta reconnect with your middle schooler in figuring out your style, because when you were in middle school, like, you were like a sponge, right? You were so aware of everything that was around you. Whether you were afraid to take risks or not afraid to take risks, I feel like that was a time that, like, you first started establishing who you were and, like, what you liked, what you didn’t like. You had an opinion about everything.
Annah Mm-hmm.
Liz As someone who lives with one middle schooler now. And I just think—
Annah Yeah.
Liz Like, the more you can channel that, the better. And I—I think the difference is, like, don’t be so hard on yourself, because in middle school we’re so hard on ourselves. We judge ourselves about everything. And I think now is the time to do middle school, like, right, and to just, like, really lean—
Annah Yes.
Liz Into the things that you love and not be embarrassed by them. And don’t, like, spend time on the things that aren’t serving you.
Annah Agree.
Marge Yeah. Be—be who your middle school self wanted you to be before they learned, like—
Liz Thanks.
Marge About other—
Annah Yeah.
Marge Pressures, or, like, other people told them no. I—
Liz Yes.
Marge I think even, like, as a kid, like, I think too, we’ve experienced so much in the last few years that—
Liz Yeah.
Marge Whether it’s, like, work, whether it’s life, whether it’s, like, the world around us, that has put so much of, like, reality into perspective that it’s like, I got this one life. I’m gonna have a great frickin’ time.
Maloree Mm-hmm.
Marge And I’m gonna go out. I’m gonna touch grass. I’m gonna do the things that my little self wanted to do or joked about wanting to do or loved doing. And I’m gonna do it without the shame and guilt that I was sort of—felt pressure to—to evolve and change. And I think you start to hit that, like, in your 30s. And then truly every year as I get older, the less I care about how I’m perceived and the—
Liz Yeah.
Marge More I care about what I think about myself and how I feel and how I—
Liz Well—
Marge Sort of go out. And I’m like, you sort of become, like, amazed, and you’re like, wow, look at what we did. Cool. Okay. And then you realize it’s just really fun.
Annah I think I’m still—I—I think at 30 I started realizing, like, all of the different boxes that people had kind of put me in that I unknowingly—
Liz Well, I think I started by closing my, so it’s not—
Marge Yep.
Annah Started identifying with. And I think I’m just now starting—
Liz Mm. Yeah, computer walks.
Annah To come out of those boxes. I think that’s where I’m at. Is, like, why—why did I let people put—
Liz That’s right.
Annah Me in boxes before?
Maloree Yeah.
Liz Totally get that.
Marge You also have experience of meeting so many people who are older than you who, in—in your old way of—
Liz Yeah.
Marge Thinking, you think should have their life together or should know what they’re—
Annah Yeah, we go.
Marge Doing, and you realize, wait a minute. They’re also just trying their best. Okay.
Annah Yeah.
Marge Or, like, they made decisions. Like, they—they chose to dress this way or look this way and—and, you know, and—and you’re like, okay, I could do that. Sure. Nobody has it all figured out, I promise. And if they do, they’re lying. Or they’re boring.
Liz No one—
Annah Yeah.
Annah Yeah.
Marge And we’re neither of that. Yeah. Yeah. Yep, we’re neither of that. I would love to wrap us—
Liz Both.
Liz I love it.
Marge Up with some rapid-fire close questions.
Annah Okay.
Marge Okay. A trend you’re unexpectedly into.
Annah Are these for me or are these for the group? Oh God. No. Okay.
Marge Sorry. These are for you, Annah. Sorry. Rapid-fire close questions with Annah. Are there any trends that you are unexpectedly into?
Annah Hmm. I have loved the—the, like, resurgence of the ballet flat. I—I—I really loved ballet flats, again, in middle school. And now that they’re coming back, I’m like, wait, I really like these. Why did I stop wearing them? I haven’t gotten any ballet—
Liz Yes, yes.
Maloree It was the smell.
Annah Flats yet, but I’m sure I will. Love that those are coming back.
Marge The arches in my feet are crying. But yes, I love that for you. I love that.
Annah Yes. I mean, yeah, there’s no support in those shoes, but—
Liz Support’s overrated.
Marge As you get—
Annah Immediately.
Marge As you get older a little, you will start to care about the arches in your shoes. But enjoy it while it lasts. Please live your life.
Maloree Ha ha ha.
Marge Okay. Is there a current confidence piece in your closet today? A piece that you love that you put on and you’re like, hmm, yep, this is it. I—
Liz Yeah.
Marge Could go anywhere.
Annah I will say, it’s kind of a subtle flex that I—I knitted a sweater that I really love, and whenever I put it on, I’m like, I made this, and it looks so—
Marge Hell yeah.
Liz God, that’s amazing.
Annah Cool—
Maloree That—
Annah And I feel great in it every time I wear it.
Marge I love that. That’s—
Liz Love.
Marge Incredible. Let’s see. Do you have a most intimidating item to shop for right now? Anything you’re like, no way, I’m—
Annah Yeah.
Marge Not doing this right now.
Annah Intimidating. I mean, I guess a—a skirt.
Liz I mean, I guess I—
Annah I gotta get a skirt.
Marge Okay. Hopefully it’s less intimidating now.
Liz We can help.
Annah Yeah, I mean—yeah, I—I—I feel like now I’m—I’m realizing, like, with the color analysis thing, that’s more so, like, for tops. Bottoms, you can do, like, whatever, right? You can go for—
Liz Yes.
Annah The crazier color. So now I feel like—
Liz Yes.
Marge You can also—
Annah That’s kind of opened up more options for me.
Marge You can also wear whatever color you want. I’m just saying.
Liz Well—
Annah Yes, that too. That too. I’m—I’m, yes. I think I—
Marge But I love—
Annah That is another kind of box I put myself in now, is like, I can’t wear that color because it won’t look good on me. But I can’t do that. You gotta pick the colors—
Liz Right.
Annah You feel confident in.
Marge You got it. You got it. I love this last one. Something you would tell Dia & Co. customers that you need to tell yourself more often.
Annah Oh man. Somebody else have an answer to that? I feel like I have to—I feel—
Marge Yeah.
Annah Like I have to think first.
Liz Well, I think that you just, like, sort of hit it on the head. Like, the rules are sort of meant to be broken. Like, I think it’s—I think—
Annah Yes, yes, yes.
Liz It’s absolutely fine to, like, learn from quote-unquote the experts or—or whatever the rules say, but, like, you’ve gotta do what works for you. And, like, sometimes rules get in the way of living your best life. So—
Annah Yeah.
Liz Don’t be afraid to—to break the rules or establish new ones for yourself.
Annah I love it.
Marge To step out of the box.
Annah Love that.
Marge I love that. Awesome. Annah, thank you so much for joining this episode and being brave. You did a wonderful job. This is awesome. This is so good. Yay.
Annah Thank you. This was fun. I maybe—
Liz This was great, Annah. Loved it.
Annah I’ll come back again one day.
Marge You could tell us about your outfit.
Annah Yeah. I’ll do a part two, probably.
Liz Yeah, we need a picture of what you end up wearing.
Annah Okay.
Marge Awesome. Thank you for joining us, Liz, Maloree. Thank you for always being here on the—on the podcast. And if folks have an SOS, you could submit your own SOS at Dia.com slash SOS. You could also read the transcript of this episode, get some style advice, sign up for a Dia Box, you know, all the fun things. And we’ll see you on the next—
Liz Probably.
Marge Episode. Love you, bye.
Liz Love you both.
Annah Yeah.
Maloree Bye-bye.

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