Whatever Happened to Worst Dressed Lists?

But did they?

Will anyone be brave enough to say that a beloved TV actor or an internationally beloved pop star dresses like a basic bitch? (Not it!) I loved Robin Givhan’s recent essay about how the MAGA movement hijacked style in DC, but part of the reason I think they look bad is because of the desecration the current administration is doing to democracy and society.

So the question still remains: If nobody looks terrible, does anybody look fabulous?

I knew who to call to tell it like it is. Law Roach, the self-described “image architect” best known for his longtime collaboration with Zendaya, has also become famous for his blunt TV commentary. I’ve watched him read contestants for filth on no fewer than three separate shows: RuPaul’s Drag Race, HBO’s voguing competition Legendary, and the most recent edition of Project Runway.

I got him on the phone and asked if he’d be willing to make a worst dressed list for me. “Don’t think I would ever answer that, Derek Blasberg,” he said, drawing out my full name so I understood the absurdity of my request.

Why not? “If I was to say that, I would not only be shitting on the person wearing the dress, I would be shitting on the person who put that person in the dress,” he said. “There should be some type of honor among thieves. I don’t think stylists should get on public platforms and disrespect the work of other stylists.”

If worst dressed lists are too mean for one of the most outspoken stylists in fashion, how exactly did we get here?

Roach takes me back to Mr. Blackwell. Born Richard Sylvan Selzer in Brooklyn in 1922, he had been an actor and fashion designer before launching his annual 10 worst dressed women list in 1960. For nearly half a century (he died in 2008 at the age of 86), Mr. Blackwell issued an annual state of the union on celebrity fashion disasters. He didn’t merely dislike an outfit; he composed insults about it. His victims became “couture casualties,” and his pronouncements were picked up by newspapers and television programs around the world. Eventually, being Blackwell-ed became something of an honor. He could be vicious. He could be wrong. But most importantly, he knew what he was looking at.

Then came Joan Rivers. Beginning in the 1990s, Rivers’s “Who are you wearing?” became nearly as important as “Who will win?” on Hollywood’s red carpets. She was outrageous, occasionally offensive, frequently merciless—and very, very funny. “She created our jobs!” Roach told me. “People didn’t have stylists until Joan would start asking people what are they wearing? She made it count. I always say that I wouldn’t have a job if it wasn’t for Joan Rivers.”

And therein lies one of the ironies. Rivers helped create the celebrity stylist, and the celebrity stylist made worst dressed critiques more complicated. Today, when an actor steps onto a red carpet, we aren’t necessarily looking at something she wandered into a store and bought herself. We’re looking at the work of a stylist, designer, tailor, publicist, jeweler, glam team, and, increasingly, a contractual relationship with a fashion house. (And if they’re really lucky, a jewelry contract—that’s who pays the big bucks.) Roach pointed out that sometimes the dress we see wasn’t even the dress the stylist wanted: Maybe the alterations went wrong. Maybe another look got stuck in customs. Maybe FedEx didn’t arrive. Maybe the client simply felt better in this one.

More recently, of course, came the internet. The worst dressed list didn’t disappear. It metastasized.

Now, everyone with a strong Wi-Fi connection is an armchair version of Mr. Blackwell, or Joan Rivers in front of an at-home green screen. Every red carpet is instantly dissected on TikTok, Instagram, X, and whatever platform was just invented while I was writing this sentence. (What is Bluesky again?)

Roach had a particularly biting observation about what replaced the old system: “Criticism has become the new way to build community.”

That one stopped me. Entire online communities are now built around shared dislike: a celebrity, a designer, a stylist, a trend, a nepo baby, a red-carpet look. The algorithm, which has never been accused of encouraging nuance, rewards outrage. The meaner the take, the more engagement it gets. Traditional fashion media may have backed away from harsh sartorial criticism, but the internet certainly hasn’t. In fact, it’s much better at it. (And by better, I mean worse.)

Which is another reason Roach isn’t feeling a worst dressed list. The internet democratized fashion criticism, but it didn’t democratize expertise. He believes unpopular opinions should exist—they should just come from people who know what they’re talking about. “These lists and these things should be curated by people who actually have some insight in the industry,” Roach said. “People who have proven that they have some sense of taste and some credibility.”

Of course, insiders have their own problem: They want to remain insiders. “You need people to do these lists [who are] not trying to get invited to the fashion show,” Roach said. Touché! The influencer wants the invitation. The editor needs access. The stylist needs the dress. The celebrity has the contract. The magazine wants the celebrity. The fashion house needs everybody. And suddenly—miraculously!—everyone looks fabulous.

Which brings us back to those participation trophies. “I don’t think that everybody should get a medal for showing up,” Roach said. He remembers when a Vogue best dressed roundup after an event might include 10 people. “Now if 85 people are at the event, all 85 people are on the list. I’m like, ‘When did we get to that point?’”

Let’s be clear: I’m not campaigning for a return to an era when women were body-shamed or publicly humiliated for choosing the wrong evening gown. The old worst dressed lists could be cruel, sexist, culturally ignorant, and spectacularly misguided. Not to mention, many of yesterday’s supposed disasters are today’s landmarks. Björk’s swan dress? Celine Dion’s backwards Dior tuxedo? Fashion history has a funny way of vindicating the people brave enough to look ridiculous.