It seems that with the release of every new Kanye West album, a new era of his personal style is also born. It’s crazy to think that nearly 20 years after he dropped his debut album, The College Dropout, Kanye is still defining today’s fashion zeitgeist. Admit it, you definitely picked up a pair of shutter shades back in the late Aughts after you saw Yeezy wearing a pair of them. And don’t even act like you never wanted to wear that Givenchy Rottweiler T-shirt he wore during the Watch The Throne tour or his iconic The Life of Pablo merch. Whether it’s Polo Bear sweaters, Maison Margiela face masks, Yeezy Adidas sneakers, and now oversized puffy Yeezy Gap jackets, Kanye’s style has never stopped evolving. And his eclectic tastes for high fashion and streetwear has led to major collaborations with Adidas, Nike, Louis Vuitton, and now Gap. And even as emerging rappers become this generation’s new style icons, Kanye’s influence on how people dress doesn’t go away. Just look at how he got Travis Scott to wear those crazy face masks he’s been using to hide his face recently. 

To celebrate the upcoming release of Donda, we tracked the evolution of Kanye West’s style—from his preppy College Dropout fits to the avant-garde pieces he wore throughout the Yeezy era.