Why Fashion Villains in Pop Culture Reign Supreme

In the fashion world, the more diabolical the compliment, the better the outfit. Those oxblood Miu Miu kitten heels are not just gorgeous, they’re to die for. That devilishly cinched Mugler blazer is snatched to the gods. Tory Burch’s pink hoop dress is more than eye-catching; it’s a certified slay. And Zendaya’s archival robot suit? Step on my neck, please. It’s serving C-U-Next-Tuesday.

Fashion insiders talk like supervillains, and they dress like them, too. PR teams wear black at runway shows as if they’re in mourning for the uninvited. Designers send models down the catwalk in unstable stilettos that could take an eye out. As far as accessories go, fashion darlings never say no to a studded bag so sharp it could cut glass. I’d rather watch Miranda Priestly deliberate between two teal belts in purgatory for eternity than spend a single hour at Andy Sachs’s Hideous Skirt Convention. Wouldn’t you? 

Of course, this is not to condone bad behavior. Conversations in fashion around sustainability, ethical production, toxic work environments, and widespread representation are necessary and long overdue. The industry needs knights in shining armor, champions of morality, and visionaries to fix widespread issues. But it also needs critics, camp clowns, and villains. In an age when “just let people enjoy things” comments bury negative fashion opinions online, no matter how innocuous, it’s worth remembering that the best of fashion commentary (think: Cathy Horyn’s searing hot takes or @sainthoax’s diligent meme-ing) calls out absurdity, making fun when the emperor has no clothes—all feelings be damned.

We—designers, stylists, publicists, casting agents, and editors like myself—hate to love the fashion villain, but we do. Perhaps it’s because cruelty reads as honesty in an industry built on as many empty promises and crushed dreams as great works of art. Maybe, just maybe, there’s something criminal about turning art into commerce until all that’s left is a toxic hellscape of masochists and sadists (a.k.a. those who buy blister-inducing four-inch platforms made of plastic on impulse...and those who sell them).

If you’re into fashion, why would you root for the hero when the villain is better dressed? Like Diana Vreeland once said, “A little bad taste is like a nice splash of paprika,” and that’s as true of real-life fashion icons as it is of editorials and photoshoots. The industry’s most famous personalities are also its most infamous. They’re the spice that makes the stew. The straw that stirs the drink.

Someone has to tell it like it is, even if they become the villain in the process.

Take fashion PR's reigning evil queen, Kelly Cutrone. With her stints on The Hills and The City, and of course, Kell on Earth, she leaned into her villainous side as the quintessential girl boss from hell. Without her shouting, badgering, and, in some cases, bullying, would the shows have even been worth watching? I think not. 

Cutrone got stuff done. She delivered tough love fashion lessons with cut-on-the-bias precision. She spoke previously unspoken truths about the industry with her own electric mix of staunch feminism and occasional savagery. She modeled the virtues of the capsule wardrobe (head-to-toe black, lots of T-shirts). She gave us, “If you have to cry, go outside”—a phrase I’ve never been able to decide is good advice or bad—all while running a wildly successful publicity empire, People's Revolution. Fashion is nothing without a bit of chaos and some brutal honesty, and Cutrone brought both in spades. 

Someone has to tell it like it is, even if they become the villain in the process—as evidenced by the late, great Joan Rivers. Already established as the funniest person to ever live (that’s a statement of fact, not opinion), the trailblazing comedian took on a new challenge in her 60s, joining E!’s Fashion Police as an on-air critic. And critique she did, roasting celebrities, throwing shade with impunity, and dragging every ill-fitting halter and misplaced sequin. Her sartorial reign of terror was so all-encompassing that I’m convinced she’s the reason celebs took so few fashion risks on 2010s red carpets.

I miss Joan Rivers. It’s been years since an on-air host has approached red carpet commentary with anything short of universal praise. Today, authentic fashion discourse happens after the event in remote, anonymous corners of the internet. But just imagine if she were at the Met Gala. Instead of TikTokers flooding the comments section with the same tired comparisons to the Hunger Games Capitol as last year, Joan would read those tone-deaf florals to filth. And we might be better for it.

The best fashion villains are so funny they practically become heroes. Thanks to a viral Project Runway compilation video that made me “ope” out loud, Michael Kors and his no-holds-barred design challenge commentary is my new villainous obsession. He said what everyone else was secretly thinking with all the humor and dignity befitting his station. “Rigatoni Mad Max” and “toilet paper caught in a windstorm” are just a few of the Korsian phrases that have since entered my fashion lexicon. I don’t know when, how, or where, but I simply must find a way to make them catch on. If Heidi Klum is Project Runway’s red carpet representative, Nina Garcia the voice of reason, and Tim Gunn the doting governess, then Michael Kors is the show’s hilariously astute Greek chorus. 

You see, good fashion (and good fashion criticism) embraces the hater within. Truly loving clothes also means hating a lot of them. By signaling, “I love this,” whether it’s through your purchasing power, your influence, your platform, or your identity, you’re also kind of saying, “I don’t love those million other things I could’ve picked but didn’t.” And if you can make someone laugh instead of cry while you put their clothes to shame, they might just listen.

Some fashion villains emerge only in hindsight. When clips from America’s Next Top Model recirculate on feeds today, it’s impossible not to marvel at the toxic conditions, questionable challenges, and problematic commentary that would never fly in today’s TV landscape. Thankfully, we’ve mostly moved past ritualistic hazing as entertainment and can now revel in the memes, memories, and kitsch of an unhinged TV show about fashion that was very much a product of its time. The series may have cast Janice Dickinson—"the world's first supermodel"—as the villain, but the premise has been lambasted in the years since, with bizarre photoshoots and camp catchphrases as its remnants. We were all rooting for you, Tyra!

That doesn’t mean, though, that we’ve transcended the trope. If 2024 is any indication, fashion villains will continue to rule our screens. At 68, Kris Jenner works harder than Satan, plotting and scheming to expand her family’s massive fashion/entertainment empire from her Calabasas lair. Alan Cumming recently joined the villainous ranks as host of The Traitors, a hit Peacock show in which he manipulates reality stars and sows discord from a remote Scottish castle while decked out in designer tartans and vintage Vivienne Westwood. On the brand front, Alexis Bittar’s tongue-in-cheek web series follows the villainous Margeaux and her psychologically abused staff as they encounter other fashion baddies like Cutrone herself and former Real Housewives of New York star Sonja Morgan.

Even fashion’s folk heroes—Alexis Neiers, Marie Antoinette, and Anna Delvey among them—started off as villains. (And for what it’s worth, Sofia Coppola has made movies about two out of three of them).

The fashion lore around these women offers more of an ethical quandary than a clear-cut triumph of good over evil. Did Marie Antoinette say, “Let them eat cake” and drink pearls, or was she just the wrong fashion girl for the wrong time, as portrayed in film and television? Her aesthetic legacy (Rococo, cottage-core, milkmaid dresses) influences fashion to this day, and so does her villainy. Just a few weeks ago, her image sparked vital discourse around class consciousness, influence, and the growing decadence of the Met Gala more than 200 years after her death.

Similarly, did Alexis Neiers wear six-inch Louboutins to her Bling Ring court date, as Nancy Jo claimed in Vanity Fair? Or, was she really wearing little brown Bebe shoes? The truth doesn’t matter, but her situation does encapsulate the toxic mix of fame, media scrutiny, and misogyny that dominated the Y2K years. Has Anna Delvey turned the life of a scammer into performance art? Or, is she a run-of-the-mill con artist? Hopefully, more will be revealed on that front, but at least we have those indelible choker-clad court photos for posterity. Perhaps Ms. Coppola should look into the movie rights?

And then there’s John Galliano. Like its folk anti-heroes, the fashion world can't seem to agree on his place in it. After being unanimously canceled by the global entertainment industry for making anti-Semitic remarks, Galliano embarked on a brief (some argue, too brief) apology tour and exile before taking the helm at Maison Margiela as creative director in 2014. It seemed his fate was to quietly fade into the sunset, toiling away from public view in the industry’s shady, avant-garde outskirts for all of eternity.

Instead, Galliano’s Margiela had its breakthrough moment in 2024 by embracing just what he was excommunicated for: his inner villain. At Paris Couture week in January, he sent a ramshackle group of ruffians, ne’er-do-wells, thieves, and conwomen down the runway, snarling in sadistic-looking corsetry and soot-stained 1930s Parisian streetwear. They wore bird nest wigs, merkins, and Pat McGrath porcelain doll makeup that glistened like a sinister Venetian mask. The collection captured the designer’s essence as an industry renegade and mustache-twirling weirdo like nothing before and, as such, became his most critically-acclaimed show in years. It was also by far his most popular, if you believe the social media views, likes, and shares; this low-fi video of Gwendoline Christie has 130,000 red hearts on TikTok alone, and Margiela's haunted doll makeup tutorials continue to rack up comments.

The fashion villain resonates, especially on social media. Margiela Tabis are no longer a fashion oddity, they’re a household name (and the subject of a viral dating horror story). This 2007 photo of Naomi Campbell doing community service in sky-high heels and silver couture is more powerful and arresting than any magazine photoshoot I’ve ever seen (and has the Instagram likes to prove it). Prada’s 2012 villain runway show, modeled by a supervillain-typecast group of actors, including Willem Dafoe, Tim Roth, Adrien Brody, and Gary Oldman, continues to go viral every few months (as it should!). Clad in ascots and velvet jackets that just scream, “I’m up to no good,” each actor served more unholy realness than the last. Clearly, there’s nothing like a stone-faced supervillain strutting in criminally sharp wares to capture our attention.

Villains frustrate, confuse, and disappoint, and fashion villains do so while looking damn good. They delight with camp catchphrases, satisfying our worst impulses as we watch them act out. They embody the dark side of fashion and shed light on its hard truths with a cutting sense of humor. After all, style is a cruel art of ruthless judgment calls and villainous dismissals. It’s impossible to like everything (and everyone) from brim to sole. Call it pretentious or sanctimonious, but much like our favorite villains, everyone’s a judgmental little hater sometimes. You really can’t have personal style without it.

So, it’s time to face the facts: Fashion is always in its villain era, and so are those of us who love it, for better or for worse. ‘Til death do us part.

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