The Rise of the Streetwear Pussy Posse

Last fall, a new set of style muses began to capture the imagination of the celebrity gossip machine. “Feeling the Jonah Chill?” read a headline on the Daily Mail in late December. “Nothing was stopping Jonah Hill from getting his newly toned legs out as he enjoyed a sport of Christmas shopping in the big Apple.” Hill was carrying a white Supreme shopping bag, and the Mail pointed out his “dove gray fitted coat, paired with a red hoodie,” his “navy baseball cap” (which read “Jerry Garcia,” aka the deceased leader of the official cult band of menswear), and his “black plimsoll shoes and matching socks” (an Adidas sock sneaker—currently on the feet of nearly every employee at Dover Street Market).

This kind of coverage has become a tabloid habit: Hill hits the streets, and his outfit makes it news. Writing in the breathless style that makes outfit descriptions sound like phone sex murmurs, the Daily Mail wrote in January of his sweater, by the British skateboarding brand Palace: “He sported an electric blue T-shirt underneath [h]is warm jacket, with black-and-white writing outlined in vibrant stripes.” In late March, the Mail praised his “black and white color block sweater” and “monochrome theme”; earlier this month, they congratulated him for “his striking new hairdo” (a buzzcut) and “[keeping] his look ultra casual in sport black shorts.” (Not everyone is a fan: the British men’s site LadBible called a coat Hill wore in mid-April for an outing with Michael Cera “one hell of an ugly coat” but said Cera “looked slightly cooler.”)

Hill is an established menswear icon: he is the subject of an Instagram “fit watch” à la Shia LeBeouf, and the hosts of the menswear podcast Failing Upwards even hosted a Jonah Hill Day party in Williamsburg during fashion week last September. But suddenly, the brands and trends that seemed to appeal to a niche set are getting a major tabloid cosign.

Hill isn't the only one pushing the look. In late February, Justin Theroux announced his divorce from Jennifer Aniston, and the gossip sites began covering him—and his outfits—in much the same way. In March, the Daily Mail captioned a photo of Theroux and Aubrey Plaza on a maybe-maybe-not date: “Something to say: Justin's top had a political statement emblazoned on the back and Aubrey had a sticker stuck to her back as they pounded the streets together.” It was a Supreme sweatshirt, a “grail” (or super-covetable item) from the first collection the brand released after the Carlyle Group valued it at $1 billion dollars that read: “illlegal business controls America.” In early April, Just Jared even made a news item out of Theroux’s streetwear shopping habits: “Justin Theroux Shops at Supreme in New York City!”

In mid-April, People reported something monumental: Theroux “was spotted out in a dark blue tank top showing off his toned and tanned arms on Saturday as the temperature climbed for the day. He paired the breezy top with his signature sunglasses and black jeans with boots. The 46-year-old actor was also seen with his trust[ed] bike as he joined his friends. One of those friends was actor Jonah Hill, who wore a bright tie-dye t-shirt for the outing.”

It was announced last August that Theroux would guest star in the Netflix series Maniac, of which Hill, along with Emma Stone, is the star, but this deep hang felt more like a significant partnership, in part because they appeared to be on Howard Street, aka Clout Alley, aka the epicenter of streetwear flexing. You could almost see the text from Theroux to Hill flash before your eyes: “Let’s link and build at The Smile To Go, fam.”

It was the official arrival of the streetwear pussy posse.

The pussy posse, of course, is the name Hollywood gave Leonardo DiCaprio and his club-hopping inner circle, revealed in a 1998 New York magazine story that attempted to chase the actor down as he partied his way through Manhattan. “They’re all about seeing the girls,” a photographer told reporter Nancy Jo Sales of DiCaprio and his friends.

But the new guard is all about seeing the grails. Supreme, Palace, Grateful Dead t-shirts, Prada overcoats, vintage tees that could have come off the racks at Procell. Garments we all know—but because our friends wear them, not because they typically appear on the male celebrities paparazzi chase (you don’t see Brad Pitt repping Palace; you can’t imagine Ryan Gosling DM'ing Online Ceramics). It’s a GQ editor’s dream wardrobe, or the kind of thing the hottest but not remotely famous guy at Cha Cha Matcha is wearing. He’s grabbing an iced latte on his way to see the new Wales Bonner collection at Totokaelo (where I saw Theroux the weekend before his divorce was announced; I’d wondered why he looked so glum even though he was clutching a Supreme bag).

Also in their crew: Harmony Korine (who was named by Sales as a member of the original pussy posse—the godfather!), photographer Jeff Henrikson, aka Jeff Henny, and…The Row designer Ashley Olsen! Rather than slinking through New York in pursuit of the next party, the next woman, the next bad decision, they’re getting iced coffee at Gasoline Alley in Noho, meeting up on Clout Alley, shopping at Marni, blasting cigs after SoulCycle, riding the fixie to Whole Foods. (Admittedly, Theroux still seems to be chasing girls, too.) Downtown New York is their Disneyland, except instead of skipping the line at the club in jeans and a t-shirt, they’re skipping the line at Supreme in an Adidas x Palace soccer jersey.

(We should note that Hill also hangs with DiCaprio, his Wolf of Wall Street co-star, but Hill is too young, and more importantly, too well-dressed, to be a member of the original pussy posse.)

But since when do we care what male movie stars wear? Aren’t they supposed to be, like, trying to dress like Steve McQueen or in a velvet tuxedo only? Celebrity theory always says that the truly famous move to New York to be “normal people”—you can walk around relatively unbothered. (Whether that’s really true is unclear; presumably Hill doesn’t enjoy the paparazzi breathing heavy whenever he “bundles up as he walks his precious pooch.”) As a source told People in February of Theroux, “He’s just doing his thing. He eats at the same time, goes to the same places, hangs with the same people.” Theroux may be a bonafide Hollywood insider with two pythons for arms, but “his thing” includes wearing the same clothing that our rich “cool guy” friends are wearing. The streetwear pussy posse suggests you can dress your way into feeling like a normal guy.

Similarly, in addition to his Normal Cool Guy outings, Hill joined Instagram in March, filling his feed with endearingly normal-sounding stuff. Theroux’s Instagram is mostly puppies and beanies, but Hill's reads like one of your friends won the lottery: he’s referring to the Proenza boys as “the GOATS”; he’s remembering A Tribe Called Quest’s Phife Dog; he’s very excited to be directing for the first time; and he’s feeling super blessed to be a part of Korine’s upcoming film The Beach Bum, which stars Matthew McConaughey and Snoop Dogg. In the comments, Hill thanks Heidi Bivens, Korine’s long-time costume designer, whose costumes for the film have already become iconic on Twitter and Instagram, because they’re like a turned-up-to-eleven version of the look the streetwear pussy posse pulls from, a kind of Biebercore psychedelica. (Bivens, you may recall, was the woman Theroux dated just before he got together with Aniston. But they wouldn’t be our bros without a little bro drama.)

Stars, we always want to believe, are just like us. They aren’t, of course, but now, they look like they want to be.