For millennials everywhere, two of the most glamorous and terrifying fashionistas of the 2000s were the hosts of TLC’s What Not to Wear, Stacy London and Clinton Kelly. London’s Cruella streak of white hair, Kelly’s herringbone suits — the polish! The fabulousness! The way they would cackle over a hapless victim’s mom jeans and dated ’80s perm before literally throwing their whole wardrobe in the garbage — well, the meanest eighth-grader you know would have to work hard to be that scary.
What was most compelling of all about London and Kelly, though, was the idea that they could actually tell you what not to wear: that there were real, rigid rules to fashion, and you could learn them, if you paid close enough attention. You could learn to wear what was appropriate for your age, your profession, your physique; to draw attention away from the largest part of your body and toward the smallest; to put together a sensible blazer with a business casual wrap dress, no matter the occasion.
What Not to Wear ended in 2013 after 10 years on the air, and Kelly and London have both since distanced themselves from the brand. Last summer, however, they announced that they would be reuniting to host a new show on Amazon Prime, one far removed from the peak of 2000s body shaming: Wear Whatever the F You Want.
“The world has changed a lot since the run of ‘What Not to Wear’, and, thankfully, so have we. These days, we have zero interest in telling people what to do, based on society’s norms — because there are no more norms!” they said in a press release. “It’s time to celebrate individual style, not prescribe it.”
Somehow, the ethos London and Kelly were trying to broadcast for their new show has become the prevailing attitude in the style advice world now. Celebrating individual style, rather than prescribing it, is the new imperative. The phrase that people — or at least the thousands of influencers who have supplanted fashion’s usual gatekeepers over the last 20 years — usually use is “finding your personal style,” and they seed it liberally in the titles of TikToks and YouTube videos and Instagram reels. As in: “Outfits I wore before I found my personal style,” “Ted talk on personal style,” “How to find your personal style.”
It felt as inaccessible as the idea that I could theoretically make a mid-career pivot to acting and win an Oscar.
I first started seeing the phrase everywhere around 2021, just as we were emerging from pandemic lockdowns, and it felt like stumbling across a mystical and arcane concept: that my personal style existed somewhere out there, independent of my conscious mind, and all I had to do was get in touch with the tools I needed to find it.
Fashion-wise, I am what the kids would call a normie. I am rarely sloppy, but I frequently feel that my clothes could look better. Imagining that I could have a sense of my own style so precise and specific that I could describe it with words, could know at a glance if an article of clothing belonged to it — well, it felt as inaccessible as the idea that I could theoretically make a mid-career pivot to acting and win an Oscar. Sure, it’s technically physically possible, but what are the odds?
Nonetheless, I was intrigued. The discussion about finding your personal style comes with such intriguing promises. The TikTok influencers and YouTube vloggers say discovering yours will save you from falling victim to trends and the accusations of basicness that come with them. It will save you from wasting your money on clothes that you don’t like, or from contributing to the mountains of lightly used textiles that clog landfills. It’s an idea that I find profoundly seductive — and, because it is so seductive, I also find myself profoundly suspicious of it.
When did we all get so obsessed with personal style, anyway?
At the outset of this decade, as fast fashion and TikTok converged, the trend cycle started to move very fast indeed. An abbreviated list of the styles that have risen and fallen and perhaps risen again in the last few years: pleated skirts, mini skirts, midi skirts; cardigans, ladyjackets, puffer jackets, trench coats; prairie dresses, maxi dresses, shift dresses; high-waisted pants, low-rise jeans, barrel cuts, boot cuts, flared trousers; tucked-in sweaters, crop tops, bralettes; lug-soled loafers, knee-high boots, platform shoes, gladiator sandals, etc., etc.
Part of the reason the idea of finding your personal style gained such currency is that it presents an antidote to this impossibly frenetic cycle. “It bubbled up first for me on TikTok and social media,” says Rachel Tashjian, fashion critic for the Washington Post. “People would say, ‘Okay, I’m getting really fed up with all of these micro trends.’ The reaction to that is to say, ‘Don’t follow these trends, but instead find your personal style.’”
One of those making the argument that it’s both more personally fulfilling and sustainable to get off the trend treadmill is Alyssa Beltempo, a slow fashion stylist and YouTube content creator. “When you know what you love, it’s a lot harder to be swayed by what’s new and what’s trending,” Beltempo says. What she means is that when you have a sense of taste divorced from the trend of the hour, you will be less tempted to buy a $20 polyester ruched milkmaid dress from Shein the next time cottagecore fashion blows up on TikTok, wear it once, and then throw it out.
Body-positive stylist Dacy Gillespie, who runs the popular fashion substack Unflattering, theorizes that the movement toward body positivity itself has played a role in the social shift that has people reexamining what they want from their clothes. If we’re able to put on our clothes without demanding they make us look as thin as possible, Gillespie argues, many new possibilities open up before us.
“I see that a lot of people are thinking more about self-expression versus what’s ‘flattering’ or what we should wear,” Beltempo says. “Both worlds do still exist, but there’s definitely been a shift.”
Or maybe there’s a more pragmatic explanation for the big shift in how we talk about clothes: the rise of stretchy fabrics like Lycra and Spandex.
“It’s almost as dramatic as when they got rid of corsets.”
David Kibbe, personal stylist behind Kibbe image identities
“In the old days, the silhouette was structured outside the body,” says David Kibbe, the personal stylist behind the hugely internet-famous phenomenon of Kibbe image identities. “A silhouette usually came from Paris, and it would change about once a decade” — hence the iconic ’40s shoulder pads and ’50s nipped-in waists.
Then came the ’80s, when new technology began to make it possible for fabric to stretch around the natural form of the body, rather than build new shapes on top of it. Today, nearly all clothes are made from lightweight and stretchy fabric, and the silhouette is no longer swapped out once a decade by Parisian designers. Instead, it’s the product of the way an individual piece of clothing drapes around an individual body. “That changes everything,” Kibbe says. “It’s almost as dramatic as when they got rid of corsets.”
Now, says Tashjian, fashion designers who used to issue edicts on what people should wear are beginning to talk about their work as being in service to the creative vision of the consumer.
“I was really shocked to hear designers backstage talking about, ‘It’s really not about what I’m creating. It’s about giving these things to women, and they can put them together in interesting ways,’” Tashjian says. “We’re used to thinking of designers as dictators.”
Changes in fabric technology made it possible for consumers to think about clothes in new ways, focusing on their own desires instead of the choices of a designer. Social media made it possible to talk about those thoughts in large groups. A growing progressive ethos of environmentalism and body positivity made it ever-more attractive to cultivate your own style. Now, it’s all that seems to matter when it comes to clothes.
The warring philosophies of style
When I first started paying attention to the idea of personal style, it was toward the end of the Covid lockdowns. I wasn’t entirely sure how I wanted to dress, but when I looked at my old closet full of prim business casual dresses I thought: “Not this.”
I wanted to know what looked good on my body. I wanted to not care if I looked thin. I wanted to feel fresh and modern. I wanted to not get bogged down in trends. I wanted lots of clothes that were new and exciting. I wanted to not spend my money on fast fashion. I wanted to answer to no one, and I wanted someone to explain clearly to me how everyone was dressing these days so that I would know what the benchmark was.
Like many people who like clothes, rules, and esoteric theory, I found what felt like a possible answer to my impossible problem with Kibbe styling, invented by Kibbe and immortalized by his first book Metamorphosis in 1987.
Over the past 10 years, the Kibbe system has become the organizing principle for a thriving internet subculture with subreddits and Facebook groups and TikTok videos — to no one’s surprise as much as Kibbe himself, who says he found out about his fan base when one of his clients told him he should search his name on Facebook. Now, it’s popular enough that Kibbe has released an updated and revised take on his system, David Kibbe’s Power of Style.
Kibbe’s system has a quasi-mystical allure partially because it’s so befuddling to figure out; it’s a little like diving deep into astrology. It contains ten image archetypes, and you sort yourself into them based on the way fabric drapes around your body. If it falls in straight, vertical folds, you are Dramatic; if it skims over you in lush, round curves, you are Romantic; if you fall somewhere in between, there’s a different type out there for you. Each type, in turn, gets recommended a different style vibe based on Old Hollywood archetypes. Regal Dramatics are supposed to look best in structured tailoring, like Lauren Bacall, whereas dreamy Romantics are supposed to look best in soft-edged, flowing clothes, like Marilyn Monroe.
Kibbe also sorts his clients into color seasons to figure out which colors look best on them — warm vs. cool, soft vs. bright. By the time his process is finished, the theory goes, you know exactly what shapes and colors flatter you, and you can ignore everything that doesn’t. In a marketplace thrown into hyperdrive by fast fashion, that’s an attractive idea.
“Personal style is hard to find,” says Vanessa Friedman, fashion director and chief fashion critic at the New York Times. “Being conscious of it opens up a whole bunch of questions that you then have to ask yourself about how you’re presenting yourself and why you’re presenting yourself that way and how you feel every morning. That takes time, and then you can start getting neurotic about whether you’re doing it wrong. So offering guidelines like seasons and shapes and all that is a way to kind of take some of the neurosis or the insecurity out of it.”
I am naturally skeptical of body typing systems, but I liked that Kibbe doesn’t seem to particularly care about making anyone look skinny. He talks a lot about “honoring” the unique attributes of each type, about making broad shoulders look broader and tall frames look taller.
Kibbe’s system has a quasi-mystical allure partially because it’s so befuddling to figure out; it’s a little like diving deep into astrology.
After I found out about the system, I spent months squinting neurotically at people’s shoulders, trying to teach myself to see the attribute Kibbe describes as “width.” Eventually, after looking back and forth enough times between my own shoulders and Carole Lombard’s, I determined that I was a Soft Natural, the same group in which Kibbe has hilariously placed such disparate figures as Jennifer Lopez, Helen Mirren, and Kamala Harris.
Finding my Kibbe type was a profoundly gratifying exercise, not least because a lot of the clothes he recommended for Soft Naturals were trending at the time. If my bias-cut slip dresses and slouchy cropped cardigans were sending a message, the message said that I was young, lived in a city, and knew what looked good on me.
Yet at the same time, I felt ambivalent about the idea of fixating on specific parts of my body, even if it was just to figure out the best ways to show them off, and on the idea of making my clothes “flattering,” which after all is still most often code for making yourself look as skinny as possible. There probably existed, I felt, some way of engaging with style that was more intellectual, purely about what you are drawn to aesthetically — so the real deprogramming could begin. The body positive and body neutral parts of the internet seemed like a good place to start.
“When I work with clients, we spend one entire hour just talking about their relationship to clothes over the course of their lives, starting with when they were young and when they got messages about what they should wear,” says Gillespie, the body positive stylist. “It’s often body related.” You could make a whole career out of teaching people to drop all the racist, misogynistic baggage we’re all carrying around with our clothes.
Even people in supposedly “ideal” bodies will probably remember being told that there were certain clothes that wouldn’t work on them. But our culture has a particularly specific slew of rules for fat people: telling them not to wear horizontal stripes that could make them look wider, or bright colors that make them stand out, or tight clothes that cling to their flesh. One of Gillespie’s goals is to help her clients learn to tune that advice out, and then figure out how to make their aesthetic dreams practical, to “translate it into something that works for them in the society that we live in.”
Gillespie points me to the example of the conventional advice for a pear-shaped person — wear fitted clothes on top that cinch the waist, and something looser and flowier on the bottom. “If you just think of that silhouette in your mind, that’s such a girly feminine silhouette. What if that’s not your vibe?” Gillespie asks. “What if you love an oversized androgynous look or something? To me that’s a really good explanation of how dressing to flatter your body could completely derail you from listening to what you actually want to wear.”
It’s for this reason that Gillespie is inherently suspicious of stylists like Kibbe. Kibbe, meanwhile, sees no point in counting the shape of your body out of the equation when you’re getting dressed, any more than he would count out the weight of the fabric.
“Everything comes down to self love and ultimately self acceptance,” Kibbe told me. “I absolutely think you should love what you wear. That’s really important.” Still, he adds, if you want to make that androgynous silhouette that you love work on your body, you have to understand the rules of how fabric interacts with your actual, physical shape. Effect relies on technique, and without it, “then that fantasy stays in your head. So I believe in integration, the inner and the outer.”
There’s a third school of thought here, however, that doesn’t just think about style as a form of art and expression, but as a form of cultural communication. Clothes come with context, and we rely on them to tell strangers things about us.
Derek Guy, a menswear blogger and social media power user, argues that having good style means understanding the cultural rules of clothing as though it is a grammar. For Guy, using systems like Kibbe’s to guide your dress choices can mean making nonsense out of your clothes’ cultural grammar, especially in the rigidly codified world of menswear. (“I don’t know anything about womenswear,” he says as a caveat.)
Take, for instance, the practice of men wearing gray or navy suits to the office if they work in traditional fields like law and finance. “That’s because of the legacy of British cultural practices: gray and navy were worn in the office in London to do business, and brown and olive were worn in the country for sport,” Guy says.
This practice clashes with the seasonal color system Kibbe and other color analysts use, under which gray and navy are cool-toned colors that only people with cool-toned skin should wear. I myself am a warm autumn, which means I would need to seek out olive or brown businesswear — which, according to Guy, may not “convey the seriousness of business.” (Truly news we can use in digital media, where people regularly take meetings in their sweatpants.)
“To me, all these ideas of dressing for your skin tone and body type are essentially trying to make what is cultural language seem like some type of pseudo-scientific endeavor, when it’s really culture that drives how we dress,” Guy says.
Skinny jeans and the trend paradox
Even after all that deep diving into style systems, even being careful to ignore the microtrends and TikTok core of the week, I couldn’t get away from the sense that every time I got dressed, I was still being pushed and buffeted by something outside of myself. I found a pair of skinny jeans from 2016 in the back of a drawer and could not stop staring at them, at how wrong they looked to me, how fundamentally incorrect. I could not believe I had ever worn anything so tight, so constricting around the ankles.
Yet I had worn such jeans on an almost daily basis for almost a decade and thought nothing of it. Why did they look so wrong now? Had I gotten so in touch with my own aesthetic preferences that I now realized I had never really liked them? Did they clash with the lines of my Soft Natural body? Were they speaking a cultural language I wasn’t interested in? Or was it simply that even after all that work, my sense of style was still under the control of the great cultural tide of trends?
Guy’s take is that if you understand the cultural language of your pants, you can still pull off skinny jeans just fine. He points to the model and stylist Wisdom Kaye, who has been posting videos of himself rocking the now-reviled skinny jean to social media.
“If you look at the outfits that he’s creating, what do they all rely on in terms of social language? Well, they all are relying on this rock’n’roll aesthetic,” Guy says. “So if your aesthetic inspiration is 1970s and ’80s rock ’n’ roll guys, you’re obviously not going to wear really wide leg pants, because that’s not the look. You’re going to wear skinny jeans. Side zip boots, flannels, black leather jackets. … That’s the look that was created through social history and will continue to be cool, because that’s the look of the Ramones, of Sid Vicious. The way that it goes bad is when guys start to wear skinny chinos with an office shirt.”
In contrast, Kibbe argues for paying attention to trends to a certain extent, and then interpreting them in a way that works for your image identity. “There should never be a subservience of style to trend or to fashion,” he says. “You should use those things in service of your star.” Then he added in slightly enigmatic tones, “A rosebud is very beautiful, but it is most beautiful of all when it’s in bloom.”
Gillespie, meanwhile, suggests looking at the problem of skinny jeans through the practical lens of your own life. “I will always try and encourage people to think about, if you’re feeling pressured to give your skinny jeans up: Why do you like them?” she says. “Do they serve a special function for you? For whatever reason, do you like having fabric close to your legs? Do you bike to work? Then I want you to consider all those things, and then reject the idea that says that skinny jeans look wrong, because you’re making that decision for yourself.”
On the other hand, is there anything more banal than not feeling like an individual in 2025? The vloggers and Substackers who talk about personal style all the time are full of this complaint. “It’s like it should be in a science fiction novel,” says Tashjian of the plethora of essays on this subject. “How is it that I’m reading over and over again, in some instances word for word, ‘It’s so hard to be an individual these days.’ And then you scroll a little bit: ‘It’s getting increasingly difficult to be an individual these days.’”
To be completely yourself: That is the fantasy of finding your style. To exist within the whole bizarre structure of fashion — all those billionaires deciding what you should wear, all those marketers deciding how you should feel about your one human body, all those materials that will lie next to your skin for some days and then rot forever in a landfill, all those people who will see you every day and make their assumptions about you based on how you look — and to feel that you’ve got some agency while you’re in there.
But the endless grind of capitalism has a way of turning all criticisms about our overconsumption into a new way of selling you things. If one of the weaknesses of our current fashion marketplace is that it’s hawking you trendy plastic clothes you would not otherwise want and will soon have to discard, and the way out is to get in touch with your own aesthetic desires — well, there are ways to monetize that journey, too.
I don’t know if we can ever find our individuality through our clothes. I did learn that I don’t really like crew necks, though.
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