Though Kendrick Lamar may emphasize the divide between himself and Drake’s OVO camp on his seismic diss track “Not Like Us,” both sides find common ground in at least one area: headwear. During his Super Bowl LIX Halftime Show, Kung Fu Kenny rocked a black backwards New Era 59Fifty fitted cap, embellished with a Rahaminov diamond brooch. And while joining Drake on his Australia tour to promote their new collab album $ome $exy $ongs 4 U, PartyNextDoor has been taking the stage in a black backwards fitted of his own. Even in war, style apparently knows no allegiance.
Lately, the backwards New Era fitted has been inescapable, like it’s 2003 all over again—spotted on everyone from Billie Eilish at the Grammys to a perplexed-looking Jason Kidd during his presser with Rob Pelinka after the Luka Doncic trade. The flipped-around early-aughts staple appears to be making a full-blown comeback.
“I think we're seeing quite a resurgence of the look,” says LA-based celeb stylist Mike Comrie, who works with Ty Dolla $ign and Charlie Puth. “I'm just seeing it pop up in the overall landscape. You're getting a lot of younger kids who don't necessarily fit the mold of hip-hop style or sports wearing backwards fitted hats these days.”
While Ken Griffey Jr. made the look his signature in the early ’90s, Comrie pins the turn of the millennium as the peak backwards fitted era, when Limp Bizkit frontman Fred Durst took a style simmering in skate parks and underground hip-hop and rolled it into the mainstream via relentless MTV exposure. “I wasn't a fan, but you couldn't escape the cultural pull of Fred Durst and the backwards red hat,” Comrie says, noting he wore one himself.
The look faded by the 2010s. Rappers like Jay-Z, Big Sean, and Tyler, The Creator shifted to snapbacks—worn frontwards, mainly—before slouchy dad hats took over in the middle of the decade thanks to stars like Bryson Tiller and Travis Scott.
“Around 2016, people would look at you like you were insane if you were wearing a fitted,” says Toronto-based TikTok creator Tresor Gray. “I got roasted whenever I tried. It just looked super dated.”
The 28-year-old recently made a viral TikTok satirizing the trend’s rise, fall, and resurrection. In it, he’s lauded for his green backwards fitted in 2007, but dragged for it in 2015, with people asking if he’s “auditioning for the G-Unit reunion tour.” Fast-forward to today, and he’s being gassed once again for the very same hat: “That fitted is so fire, bro.”
He first noticed the look creeping back around the pandemic. “I was against it at first. I was like, yo, there’s no way I'm wearing fitteds again. I already got rid of all mine. It’s over,” he says. But resistance was futile. “Now I’m like, you know what? It actually does look a little fly. Let me tap back in.”
Some credit the fitted cap’s resurgence to Hat Club’s “pink bottom” movement, spearheaded by lead designer Justin Farnham. The trend exploded during the pandemic, but its roots go back to May 2019. At the time, Farnham was managing Hat Club’s NoHo store when his friend, rapper Darius “Frosty Preme” Drumright, asked him to create a Yankees cap with a light pink undervisor to honor his late mother, who had passed away from breast cancer, and a 1996 World Series patch, nodding to his birth year.
After getting approval from New Era, they made a limited run of the hat “just meant for the homies.” But it caught fire fast. When Hat Club NoHo dropped a pink bottom collection in October 2019, customers lined up around the block to get their hands on one. Farnham followed up with several iterations—including the Watermelon, a forest green crown with a red undervisor—each selling out just as fast online.
“All of a sudden, people started treating them kind of like sneakers,” Farnham says, adding that fitted sales have increased “1,000%” in the past few years. Celebs now frequent his NoHo shop, from David Beckham to Justin Bieber—the latter recently copping a Phillies cap in the off-white and dark green Panna Cotta colorway. “We went from a small warehouse in Arizona to one that’s as big as a Costco,” he says. “There’s tons of workers and hats to the ceiling.”
Custom fitteds have since become something of a cottage industry, says Leon Chen, a cap designer for Pro Image Sports Colorado. His company is one of several putting their own spin on the classic style. Brands like Alice Hollywood, Yohji Yamamoto, and Styll have been rolling out creative interpretations as well, with flourishes like pins and dog ears.
“The job of hat designer wasn’t a thing before. The pandemic really jump-started the craze. There was a captive audience and a lot of hat content being made at that time,” says Chen, who launched his own hat-centric YouTube show, Views From the Vault. “People were just buying hats online like crazy.”
But what of the tendency to flip it and reverse it? Chen says he’s clocked more celebs, from Bad Bunny to Bieber, wearing backwards fitteds as of late. While fitteds have been bubbling up for a minute, he believes rocking it back-to-front is a relatively new phenomenon. And an old one too. “It was always kind of a sign of being a rebel in the ’90s. That Kriss Kross era,” he says, referencing the hip-hop duo that committed style mutiny with their inverted clothes.
There’s always been an air of insubordination to the flipped-back 59Fifty, says Josh Roter, co-owner of Toronto’s In Vintage We Trust. When Griffey Jr. wore his Seattle Mariners cap backwards at the 1993 Home Run Derby, it was a visual act of defiance against the clean-cut, uniform expectations of pro sports.
“He made what was traditionally a team sport about himself. That was a big faux pas in the world of baseball, because it was all about the logo on the front of your hat, not the number on the back of your jersey,” he says. “And on top of that, the fact that he wasn't a white guy doing that, in the ’90s, was probably seen by the powers that be as a big no-no.”
Roter has noticed a surge in Yankees fitted sales, attributing it to the Y2K fashion revival. While Spike Lee was the first to don a red Yankees cap after requesting the colorway from New Era in 1996, Roter believes younger customers are more likely drawing inspiration from Fred Durst—the most "digestible and overt" figure from that era. The aggro icon is also the reference point most likely to get people to take a look around their fits.
“Young people are trying to get a reaction, and they know Fred Durst—and wearing a red cap backwards—will get a certain type of reaction,” Roter says. “And just the idea of wearing a hat backwards means that you're counter—like, you're against the grain.”
Comrie, the stylist, believes the backwards fitted reflects a growing "fuck the system" mindset fueled by, well, everything going on. “Kendrick's Super Bowl performance was centered on themes of rebellion and protests and recognizing divisions. I think the backwards hat is symbolic of that, whether or not (it was intentional),” he says. “It embodies where a lot of our culture is mentally at this time. I think a lot of us are feeling like things aren't going the way that we would like them to be going. There’s a general desire to just go against the status quo.”
So, the reversed fitted may well be the first flicker before the revolution catches fire. Who knows! Either that, or it’s just a sick way to sport a hat that looks good on many people.
“If you’re wearing a snapback but your forehead is big, it looks kinda weird with it showing in the middle hole. And dad hats just look bad if your head isn’t slim enough,” says Gray. “But if you don't like your head shape or your hairline, the best hat to wear is a backwards fitted.”