In an era of ultrafast fashion and rinse-and-repeat trends that all sort of feel the same, there seems to be a shortage of true personal style. The kind of distinct wardrobe that feels original and inspired. Something fresh.
Not that it's easy to find one's sense of style. How do I want to dress? It's a surprisingly complicated question. Internet micro-trends might seem like cheat codes, but TikTok’s-core du jour often says more about your algorithm than anything specific to you. Even when you do manage to develop a fashion identity, it’s always subject to change; life events—motherhood, a career pivot, a loss—can sever your connection to clothes and require a re-thinking of how you dress. And just like that, you're muddling through fashion influencer feeds and newsletters and trying to figure it all out again.
Which is why we've asked some of the most authentically dressed women we know to share their own personal style journeys. They span generations and professions. But they all have powerful points of view on how to define and create your own personal style.
Finding your style really starts in your mom's closet as a kid...
Taylen Biggs, 11, content creator
Her style in three words: Confident, me, and a boss.
On the youthful joy of fashion: A lot of people think that fashion is just for adults, but that's not true. Finding your style really starts in your mom's closet as a kid; you go in, grab your mom's heels, and walk around the house with her heels on—do, do, do, do! Then, you go into her makeup and try on her eyeshadow and lipsticks.
I was that kid. I don't really remember it because I was a baby, but I played around with my mom’s stuff and started [exploring fashion] just by having fun. I've been really into accessories all my life; I'm all about earrings and necklaces, and shoes are my everything. Ever since I was little, I’ve been really into bright colors. Playing around [with clothes] was how my style started, and I’m still having fun with it.
A memorable moment in her style journey: I got really into red carpet fashion during Covid, and I remember seeing Billy Porter’s red carpet look at the 2020 Golden Globes. He wore this white look with a jacket that had a train entirely made of feathers and looked like a swan. I almost had a heart attack. It was so exciting. [Porter’s look] helped me see that fashion is art and can transform into anything you want to be. I was really able to tap into my style after that.
An outfit that transformed: When I went to the Elisabetta Franchi Spring 2024 show in Milan, I wore this gold sparkly custom ‘fit with a beautiful cape attached to the back. I felt really good about myself in it because I love structured pieces—there's something about high shoulders that just really speaks to me. I was there for business and I felt powerful—like I was a fashion superhero.
How she'd style a white T-shirt: I styled a classic white tee when I was the red carpet host for the Chiefs’ Super Bowl Ring Ceremony in June. The white tee was my canvas, and I wore gold sparkly pants that gave cheerleader-confetti vibes. Then I added this really beautiful Balmain blazer with statement buttons and high shoulders. The blazer was everything.
It's important that my fashion be reflective of my feistiness and indifference.
Jasmine Crockett, 43, civil rights attorney and US congresswoman
What she thinks about when getting dressed: I try to be mindful of what the day will look like scheduling-wise—and hopefully dress better than others.
How her job influences her style: Figuring out what a younger congresswoman looks and dresses like has been the most interesting part of my style journey. For people to credentialize what you say as a professional, they expect you to look a certain way. It’s important that you dress for success, as they say. So, how do I define myself so I look like what people perceive to be a congresswoman, but also so I don't look like I'm 70?
I don't want to wear the same things that older congresswomen wear. It's important that my fashion be reflective of my feistiness and indifference. I love to wear a plain suit but jazz it up. I’ve started wearing more brooches, rings, and accessories to bring a little bit more life to my outfits. That’s as feisty and bold as you're going to get in the House.
A recent fashion lesson: Even though black is my favorite color, I've started exploring more bright colors. That was something the older members [of Congress] told me. 'You’ve got to wear more colors because your constituents want to see you.' If you end up in scenarios like the State of the Union, for instance, [wearing colors] makes it easier for your constituents to find you.
A style non-negotiable: The most important part about your wardrobe is making sure the items fit well. You need to make sure that you're really comfortable with the fit of your clothes because everything else kind of falls in line after that. The better they fit, the more confident you'll be, and the better you'll wear it.
When I was in New York recently, I had to do a press appearance that I hadn't anticipated when I started my travels, so I didn't have a suit with me. But I knew I could go to Banana Republic because the fit of their jackets and pants works best for me and is the closest to a tailored fit I could get right off the rack. I ignored all the big designer stores in New York and went straight to Banana Republic.
How she'd style a white T-shirt: The first thing I think of is jeans and a blazer—and a cute spiked heel, like these amazing black and spiky Steve Maddens I have. I would probably make sure that I put on something else spiky in my jewelry, like a bracelet, and also mix in a little bit of softness, potentially with pearls.
A lot of the internet is designed to make us feel hyper-self-conscious, so doing away with, 'Who am I? What is my style?' can take your focus off of yourself and lead you to more interesting places.
Tavi Gevinson, 28, writer and actor
How she'd describe her style as a teen: When I was a kid, fashion was like arts and crafts to me. [My outfits] were like collages, and my clothes were images that I liked combining in interesting ways. I didn't have any sense of whether clothing technically fit or not; it was more about the idea of what I was wearing. My actual appearance was so beside the point because I was too young to have much vanity around how I looked, thankfully.
I would give myself prompts; one week, I would try to dress as a different planet every day; the next, as different book characters. Because Rookie [an online magazine for teenagers created by Gevinson] was so inspired by Sassy Magazine and Riot grrrl, I also enjoyed dressing like I was going to a basement show all the time.
And now: At this moment, I see whatever in my closet excites me or gives me a visceral, eye-candy response, and go where my instincts take me. I try not to overthink it now.
How her style is still evolving: The era of fashion when I first became interested in it as a kid still looms really large in my mind—Prada, Miu Miu, and Marc Jacobs from 2008 to 2010. But I'm trying to find the relationship between the cute, really feminine stuff I loved when I was younger and now being 28 and, like, What do I get to wear now that I felt too young for as a kid? I'm figuring out how to keep that childlike part of me alive but also not look like I'm 12 because I want to enjoy being in my late twenties.
It’s all pretty basic, being a woman and growing up stuff. And this is why I love clothes: you form different associations, attachments, and memories to different symbols, colors, or whatever, and then you're refashioning your relationships to all those things over time.
On micro-trends: I don't really care about authenticity when it comes to style. At this point in our civilization, it would be hard to be a purist about where someone’s fashion impulses come from. [An internet micro-trend] can be a story you tell about yourself, which sometimes helps you discover another part of yourself. But all these labels and crazy sub-sub-subcategories—cottage-core, or whatever—are sites where you, your style, and other expressions of personal identity meet the world. But it's not where you begin or end.
A lot of the internet is designed to make us feel hyper-self-conscious, so doing away with, Who am I? What is my style? can take your focus off of yourself and lead you to more interesting places. It's kind of like, if you're thinking really hard about your writing voice, you're not focused on the thing you're writing about.
How she'd style a white T-shirt: I like a white T-shirt with a skirt that really draws attention to itself and some very simple sneakers, like Adidas Sambas.
Age will not affect your love for fashion.
Dr. Qui Huilan, 70, retired doctor
On her son being her style muse: I don’t understand fashion. Because I was a doctor and was busy in the hospital most of the time, I didn’t have the time [to get into fashion]. My son, who was an art major, started buying art magazines when he was in middle school, and I would read them at home. I liked the beautiful pictures—the clothes, the models. I got into fashion because of him and started posting my outfits on social media in 2022.
Actually, most of my clothes are from my son. Looking at my Instagram, you can tell that most of what I wear are men’s clothes. I can't give an accurate answer on what my favorite item of his to wear is because I am a greedy person, and I think every piece of clothing in my son's wardrobe is very beautiful.
How she transitioned from a minimalist to a maximalist: When I was young, I dressed more conventionally, usually concisely and comfortably. After all, my work required me to wear a white coat every day, so that’s what I wore most of the time. Now that I am retired, I prefer a combination of various colors.
The benefit of discovering fashion later in life: Age will not affect your love for fashion. I want to encourage everyone to try new experiences as they get older because I believe their beautiful energy and passion should continue to pass on…
Before the age of 70, I only cared about my patients as a doctor, but I have experienced such a fantastic journey since [retiring]. Friends from all over the world praise me and leave comments on my Instagram. I’ve met and talked with Mrs. Prada. I traveled to Europe for the first time to walk the runway for my favorite brand, Miu Miu. Who would have thought that at 70 I would be standing there on the runway? It was also my first time walking the runway, and I think I did a pretty good job. Didn’t I?
How she'd style a white T-shirt: I will write the slogan "wondullful." Yes, the middle is "dull"—it is really just a dull white T-shirt—but it looks "wonderful."
Style comes from that thing inside you that makes you feel confident. It doesn't matter what you're wearing, really.
Caroline Vreeland, 37, singer, actor, model, and "most importantly" mother
How being a mom changed (or not) her style: Oftentimes, I dress like two different people. I'm the mom in Montreal who wears flip-flops for six months in the summer and Uggs for six months in the winter. Then, I'm this glamor-puss who jets off to these amazing jobs in Europe, works with a stylist, wears these crazy things, and lives this flamboyant side to my character.
It feeds my soul to be able to be both women at the same time. That glamorous girl is still here, but I have a higher purpose now. Fashion is such an elite world; you always have to know the coolest people and get into the coolest places. But now the coolest place is the floor of my living room with my kids. I don't feel the need to please anyone because the real thing that matters to me is back home.
On confidence being crucial: I don't know what I'm doing at all with [fashion], but the one thing I know is that I have confidence. Style comes from that thing inside you that makes you feel confident. It doesn't matter what you're wearing, really. Azzedine Alaia said, 'I make clothes; women make fashion.' Alber Elbaz said a similar thing: 'A good dress disappears when a woman wears it.' There's this nugget, this fire, inside you, and that's really what comes across when the outfit is working.
That sense of confidence isn’t easy to get. You can’t just go out and find that self-love. It takes a lot of inward work to get to that point, and I wouldn't say I am anywhere close to nirvana. But now that I’m older, I don't really care what anyone has to say about what I wear. I'm more comfortable in my skin and can wear what I want and still feel great in it. I literally will wear Crocs and my husband's sweatpants and walk into the daycare center like the hottest bitch you've ever seen.
How her great-grandmother and renowned fashion editor Diana Vreeland inspired her: [She] really believed in showing people that their flaws were the coolest thing about them. She did Barbra Streisand's [March 1966] Vogue cover and wanted the nose. She loved Mick Jagger's lips [in the 1964 Vogue portrait by David Bailey]. She showed that what you think is the weird thing about you—the thing that is different—is what you should honor and highlight because it's uniquely you, and that's the sexiest part.
For me, that's my boobs. I know it sounds like, 'Boo-hoo, you have a nice rack!' But I know what it's like when you don't fit into what everyone else can wear. I realized that, okay, I am in the fashion industry and have this difference, but instead of letting it work against me, I can trailblaze it. I can show girls that you don't have to feel sloppy or messy or too big if you have a body and boobs. Big tits aren’t a deterrent for entering the fashion world.
How she'd style a white T-shirt: I would just go Americana and simple: good Levi's cutoffs and my black Adidas Sambas.
Break all the fashion rules you have ever known. Don’t care what people have to say.
Helen Van Winkle, 96, social media icon
How she'd describe her style: My personal style now is comfort with glitz. I also love tight-fitting clothes; I have a great figure for a 96-year-old. I love color and being fearless with clothes. I dress some days to feel alive. Other days I just want to wear a polka-dot robe. My bedazzled cane is always near and dear.
On the evolution of her adventurous approach to fashion: I’ve always been interested in fashion, but when I was younger, I tried to fit in too much and keep up with the times. But don’t get it twisted—I still dressed. Even though I never had much money, I always found a way to explore myself through clothes.
But with getting older, I realized more than ever how good I looked. I began to feel so empowered with putting myself out there. I’ve really had a ball, and I know I’ve helped a lot of people get out of their own way by showing that it’s never too late to transform your style. We all know how old we are physically; what matters is how we feel internally. Age doesn’t matter when you look and feel good.
Her advice for discovering your own distinct style: For someone who wants to be more playful, go to your closet and play. Try on some new things. If you don’t have anything, go to a thrift shop or boutique and buy something that’s out of your comfort zone but still resonates with you. Start small; introduce a new color or a bold print, and accessories are really a fun way to start.
Break all the fashion rules you have ever known. Don’t care what people have to say…because you look good. You have to know that first.
