With the arrival of Netflix’s ‘jeen-yuhs’ documentary about Kanye West, we decided to take a look

back at his style evoution from ‘College Dropout’ to now.

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, or industrial Red Wing boots mixed with Yeezy Gap

Round 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.

Even as emerging rappers become this generation’s new style icons, Kanye’s influence on how

people dress doesn’t go away.

To celebrate the release of Netflix’s three-part documentary, jeen-yuhs, 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.

‘The College Dropout’

Key Pieces: Rugby polos with a popped collar, blazers, Louis Vuitton backpack, Polo bear sweaters

Kanye West knew from the start that his style would play a huge part in his persona. And with a debut album titled The College Dropout, he dressed accordingly. Kanye presented himself as a preppy-leaning backpack rapper with a penchant for Polo, which was greatly influenced by Chicago’s ​​Reggieknow, a well-dressed Lo-head and illustrator graffiti who threw Dam Dare parties and dressed unlike most of his peers at the time. Kanye wore popped collars, bright colors, pink polos, corduroy blazers, rare sneakers, and an actual Louis Vuitton backpack. Polo has always been a staple within Black culture, and the backpack rapper look wasn’t an entirely new concept, but Kanye’s preppy style was different from how his peers dressed in the early 2000s (oversized T-shirts, baggy jeans, matching denim sets). And it resonated with fans, who not only embraced his music but his style, too.—Aria Hughes

When: 2005

Key Pieces: 70’s style suits and tuxedos, aviator sunglassesBy 2005, Kanye had commercial and critical success with The College Dropout and more money.

When: 2007
Key Pieces: Loud designer and streetwear pieces, shutter shades, keffiyeh neck scarves, and Takashi Murakami Jesus pieces

Now if we turn the clock back to the Graduation era, this was when Kanye West started dabbling in high fashion. We started seeing Kanye West brush shoulders with designers like Karl Lagerfeld and Marc Jacobs at Paris Fashion Week. A transitional period for Kanye, this was an era when he began shelving the preppy vintage Polo fits to wear more contemporary streetwear and luxury pieces. He traded the pink Ralph Lauren polo for pieces like a Comme des Garcons x Fred Perry shirt along with his Takashi Murakami-designed Jesus piece and Louis Vuitton “Millionaire” sunglasses. Then, Kanye would switch it up and wear some more outrageous pieces, like that infamous “Dead Serious” LRG hoodie. But when you remember that Kanye was hanging out with eccentric style icons like Taz Arnold during this period, it’s not surprising that he came up with some of his most unique fits around this time. Who would have thought that the ridiculous accessories that Kanye wore during this moment would become full blown trends that took over the world? He really had everyone wearing “Shutter Shade” sunglasses, for example. And anyone who has ever worn a pair knows damn well it’s nearly impossible to even see where you’re walking when wearing those. But really, wearing them made you feel like you were ready to bust through some drywall like Ye did in the music video for “Stronger.” The Gradutation-era of Kanye West was also filled with neon colors and futuristic looks, like that LED embellished band jacket he wore when he performed with Daft Punk at the Grammy Awards. Although some style trends he pioneered during this time didn’t age well, like Kanye’s high-fashion takes on keffiyeh neck scarves, this moment of Kanye’s style was still undeniably influential.—Lei Takanashi

He was still playing in the college/academia theme, hence the name of his second album, Late Registration, but he was no longer the emerging backpack rapper. Kanye’s style got more refined and 70’s influenced, which aligned with his music that sampled soul songs from that era. He started wearing well tailored tuxedos and suits styled with button down shirts that revealed his chest, knits layered over collared shirts, and oversized aviator sunglasses—the 70’s comes through in a big way for his “Touch the Sky” video, where he dons thick sideburns, a pink collared shirt and white tuxedo pants. We also see it at the 2006 Grammys, when Kanye wears a lavender tuxedo with white satin lapels. By this time, Kanye hasn’t ventured into designing product, but that would come shortly after.—Aria Hughes