
The Free Press

There’s a troubling trend afoot.
No, it’s not that a bunch of unelected coder-crats are rummaging through the file cabinets at the Pentagon. (Long live the DOGE boys!) It’s not that natural disasters are threatening our cities, or that AI is threatening our sense of a shared reality.
It’s that comedians are dressing a little too well.
Christopher Hitchens famously argued that women aren’t funny. Which is bad news for me—it’s sort of the only thing I got going. But I’ll hang this tassel to his stake in the ground: Professionally funny people should not also be fashionable people.
When I see a guy step onstage who looks like Louis CK, sweating through a T-shirt bought at Costco, pants worn so many times they’re verging on skin, I know he is going to deliver the goods. If he’s hot—which in comedy used to just mean having a visible chin—I’m skeptical.
What’s a girl who looks like Lily-Rose Depp going to make jokes about—how it sucks to have perfect bone structure? Female comedians have different rules (and yes, I make the rules). Gilda Radner was a beauty but she presented like a college senior studying in the library for finals. Julia Louis-Dreyfus drowned in the floral dresses and shoulder pads she wore on Seinfeld—but the wardrobe, along with her huge hair, helped define “Elaine.” It would not have landed if she’d worn athleisure to Jerry’s house. Ratty cardigans and bad shoes on a female stand-up tell the audience “go there with me.”
For people whose job is to get people to laugh, looking bad is good. It helps to come across as self-deprecating, or relatable—even after you’ve become a superstar.
30 Rock was a send-up of the Saturday Night Live writers’ room—and they had a lot of fun with the fact that the writers were horribly dressed, verging on sexless carnies. This was true especially for Tina Fey’s character, Liz Lemon. “Lemon, the grown-up dating world is like your haircut. Sometimes, awkward triangles occur,” Jack Donaghy, played by Alec Baldwin, deadpans. Jack Donaghy, from season 3: “Nice dress. Are you going to dinner? Don’t forget your book.”
And yet the comedy-to-couture pipeline is strong, and getting stronger.
This past weekend, celebrating 50 years of SNL—an anniversary that’s gotten more attention than V-E Day—Tina Fey arrived in a Dolce & Gabbana cocktail dress and Fred Leighton jewels. She had a total of three outfit changes throughout the night. Leslie Jones worked the carpet in a slicked back ponytail and a Versace number. All the former cast members waltzed through in black tie—they looked like hedge funders at a museum benefit.
Or take the spread that Elle magazine put together with all of the women currently in the cast. The women are swathed in expensive-looking taupes, creams, and beiges—all structured jackets and nude kitten heels— deadly serious in quiet luxury. The smoldering group, which includes Heidi Gardner, Ego Nwodim, and other genuinely funny women, look less likely to deliver a punch line than the news that the tumor’s malignant. They seem like they’re about to scream at a waiter, rather than crack you up.
Pete Davidson—who could, for years, reliably and thankfully be found in flip-flops, sweatshirts and pajama pants—is now in a new ad campaign for the brand Reformation. Gone are his goofy and colorful tattoos, and his sickly, sticky frame. Instead, Davidson, muscled up and tan, is doing a Calvin Klein pout at the camera in white undies, and in another shot scowling shirtless in cream pants.
Hannah Einbinder, the star of Hacks, hit the red carpet at this year’s Critics Choice Awards in a custom Louis Vuitton number so severe it’s architecturally significant. Bowen Yang has a penchant for Valentino and employs his own groomer.
What gives? These people are clowns. Clowns are wonderful! They are my favorite people. But clowns don’t wear Loro Piana or Brunello Cucinelli. Clowns should not have glam squads. They should not have a creative director to thank.
Chloe Fineman—who wore a 50-year-old vintage Guy Laroche couture for SNL’s 50th— told Elle she considers being “being chic and glamorous” rebellious in the comedy world. And for good reason. Fashion as an industry is the opposite of comedy—it’s fussy and obsessed with perfection. It’s serious, and up its own ass. Clothes can have a sense of humor, but they can’t actually be funny. And when funny people start playing ball with high-end brands and gushing over their favorite atelier, it comes off as elite and out of touch. Fineman looked gorgeous, but intimidatingly cold.

Besides, comedy is the rare art form where being oddly shaped and woefully, outwardly uncool is an asset. Not to be rude but: Jackie Mason, Ellen DeGeneres, Kevin Hart, Wanda Sykes, Artie Lange, Eddie Izzard, Melissa McCarthy, Rebel Wilson. To name just a few. Comedians need to look like Tim Dillon—his body defies physics, he refers to himself “as a fat,” and he told Megyn Kelly his aesthetic is “retired detective”— for me to trust them.
Not to say that comedians can never be hot. I’m happy for Tina Fey that she bought a beautiful dress and has a trainer now. No one should hold it against Sarah Silverman that she was blessed twice. But she uses her goods to elevate her shtick, not her chances of getting invited to a pre-fall runway show. Overalls, pigtails, and low-cut shirts helped bolster the slutty-wholesome thing she was playing up. Even Joan Rivers, who buried herself under gaudy jewelry and fur coats, did it to, if not intentionally for, comedic effect.
The point of the funny fashionistas seems to be: Being funny is a role I play on TV. Really, I’m a celebrity—and a hot, cool one at that. Fifty years after SNL began, I have a proposition: Make Comedians Ugly Again. Or at least, poorly dressed.