And that's a good thing.
If you were a rebellious teen in the late '90s and early 2000s, black jeans, spikey belts, trucker caps, and your favorite emo band tees are all too familiar (we know the pictures are out there). But while you were busy jamming American Football's album in blacked-out Chuck Taylors and over-padded skate shoes and hanging with your friends at Hot Topic and Spencer's Gifts, Raf Simons was channeling youth culture into his label, slowly but surely spinning it into one of the most influential menswear brands of the past 20 years. These black and red canvas sneakers, made in collaboration with Adidas, balance nostalgia for that specific era of "screw you mom!" style with Simons' high-fashion taste level.
You could wear these sneakers with some other Raf Simons pieces, from his grail-level fishtail parkas to his just-released oversized sweaters, but the GQ-est move would be to rock 'em with the thing that first got Raf attention in the '90s—a slim black suit. You'll still feel the nostalgia while showing the world you're all grown up (and that, okay, you're sorry for yelling at your mom).
$330, available at saksfifthavenue.com