A$AP Rocky tracks time with fashion. “I remember years by outfits,” he says. “When you tell me [what I had on], I remember.” Vogue put one of our May cover stars—and esteemed 2025 Met Gala co-chairs—to the test with the latest installment of Life in Looks.

Fashion has always been central to the rapper’s identity. Long before Rocky and Rihanna graced the Met steps or announced her first pregnancy with a fashion-filled paparazzi shoot, they united for his “Fashion Killa” music video. “I just hit up the flyest chick that I knew,” Rocky says of casting his now-partner in the video. “I’ve got the perfect song. It’s called ‘Fashion Killa’—I’m basically talking about you; I drop your name in it.” Even though it was 2013—more than six years before they would become a couple—Rocky maintains that there was always that spark. “She knew she was my boo back then too,” he says.

Rihanna wasn’t the only major name attached to the “Fashion Killa” video: Virgil Abloh directed the project. “Working with Virgil was easy. We were kindred spirits,” Rocky says. “I think that him being in the position he was in, it was inevitable for him to do great things.” The late designer was just one member of the fashion community Rocky counts as a friend. Others include Alessandro Michele and Jonathan Anderson. “I pick his brain from time to time whenever I get to speak to him,” he says of the latter.

Not every outfit in his extensive repertoire may be a hit with his fans. “I ain’t gonna lie, they roasted me on the internet for this,” he says of the yellow Balenciaga puffer vest he wore in Milan in 2017. “This outfit was kinda fire if you think about it…Nah, I was wilin’,” he says. “That’s my Flavor Flav era right there, you know what I’m saying? It was tacky but fly.”

But when the risks work, they work. “This was a daring fashion statement. I chose to embrace being a grandma’s boy,” Rocky says of his babushka era, where he would wear floral Gucci scarves around his head like a grandmother. “I’m a firm believer that you can’t use clothes as masculinity anymore. Those lines are blurred as well, so I like to play with that. And I thought it was unfair that guys couldn’t wear a silk scarf on their head with glasses,” he says.