Awake NY and Gap’s new collab is a love letter to ’90s New York

As far as Angelo Baque is concerned, Gap belongs in the canon of ’90s New York street style. For the Awake NY founder and designer, his introduction to the something-for-everybody brand came before his inevitable descent into Polo, Hilfiger, and Nautica—the holy trinity of the city’s swaggering, hip-hop-inspired style in that era. “Gap was always a part of my life,” Baque says. “It was one of those staple brands. It was what you wore when you stepped out into the world.” Now, Awake NY and Gap are paying homage to that golden age with a new collaboration set to launch this week.

Before Baque became a New York streetwear lifer—growing Awake into a downtown institution after an influential stint as Supreme’s brand director—he was just a kid in Queens who learned about everything cool from his older sister. He recalls watching her put outfits together before heading out into the city’s club scene—an early education in the links between music and style, personal expression and youthful attitude. And a major part of those outfits was a specific green Gap anorak his sister loved. “I used to steal it from her, and she’d try to beat me up every time,” he says, laughing.

The collaboration leans into those memories, mixing Awake NY’s bold visual language with classic Gap items: logo hoodies, heavyweight fleece, reimagined denim, graphic T-shirts, and other accessories. There are pops of color and polka dots and plenty of sharp screenprints, and much of the gear feels just right for loud nights at the club and casual hangs on the stoop. Prices range from $18 to $268.

With younger generations now circling back to ’90s and Y2K trends—with the Gap of that era especially hot again—Baque sought to honor that aesthetic while still giving it some contemporary topspin. “I think they want something that feels real,” he says of Gen Z shoppers. “The art and the fashion that came out at that time wasn’t influenced by the internet. There was no algorithm to influence the style or the music.” While designing the collection, Baque referred back to the brand’s 2001 TV spot featuring Skratch Piklz and Shannyn Sossamon, as well as the print campaign starring Erykah Badu and her sister Nayrok from the same year.

But Gap x Awake NY offers more than a yearning for the past. It’s a love letter to a moment in New York nightlife when the clubs weren’t musically segregated yet, when the wide-ranging mix itself was the draw—and the fantastic style on display was a mere aftereffect. “Clubs didn’t just play hip-hop,” Baque says. “You had to play hip-hop, house, freestyle, reggae.” That same sensibility showed up in how people got dressed—polka dots, bold plaids, baggy jeans, chunky shoes. It didn’t always make sense on paper, but that was beside the point. Baque isn’t trying to recreate the past so much as remind us that it happened and that it mattered. Like the music, the fashion was light on rules and heavy on rhythm. The point now is keeping that rhythm alive, so the next generation can find their own way in.

The Gap x Awake NY collection launches Friday, March 27 on gap.com and at select stores.