2016 can be marked as the year that ASAP Rocky completed his ascension from streetwear star to bona fide high fashion habitué. With the help of consistently killer front row style—see his Gucci Resort 2017 look—and his appointment as the new face of Dior Homme, Rocky became the “Fashion Killa” that he rapped about years ago. What’s been truly great about Rocky’s rise is a few things that have remained true; he hasn’t turned his back on any of the hallmarks that made him him. Rocky is still very Harlem jiggy, as evidenced by the floor-length mink he rocked at the Yeezy Season Three presentation. With his nostalgic Guess Jeans collaboration, he’s shown that he hasn’t forgotten the great streetwear brands of his youth. And no one can rock a classic ’90s style moment quite like him: white t-shirt tucked into light blue jeans, casually cinched with a belt, and topped with a black sport coat. Rocky is the rarest of style dudes; a man who can naturally embody the past and present with the ease of a furry Gucci mule. —Deidre Dyer
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