In the early 2000s, at the outset of his career, Ye (formerly known as Kanye West) announced his plans to be the best dressed rapper in hip-hop — and he spent the next 20 years proving that point. This aesthetic journey began with a kaleidoscopic flurry of colorful Ralph Lauren and Lacoste polos, popped collars, jean jackets and striped sweaters; Yeezy found countless ways to get fits off, blending mainstream drip with his own personalized touches as he became a global superstar. 

While Ye’s fashion quest is still underway, the release of jeen-yuhs: A Kanye Trilogy made us want to revisit Yeezy’s inimitable Y2K style. Peep the breakdown below. 

Polo rugby

In the early going of his career, Ye differentiated himself from other rappers by embracing prep in an era of throwback jerseys. One staple of Y2K Yeezy drip was his Ralph Lauren polo rugby, which he rocks at various points in jeen-yuhs. He has referenced the brand in a bunch of lyrics, too, rapping, “Ralph Lauren was boring before I wore him,” on Rhymefest’s 2006 song “Brand New.” 

Popped collar

Another staple from Ye’s College Dropout era was the popped collar. Whether he was rocking a sweater or a blazer, Yeezy collar-popped that bottom layer’s collar in all its flamboyant, early ’00s glory. 

Bucket hat

Although he wasn’t always rocking one, on the day Ye signed to Roc-A-Fella Records — and at various other points during the era — he was wearing a bucket hat. Naturally, this accessory was phased out of his closet as time passed, but it was definitely a look for the moment. 

Movie tees

At the end of the day, Ye’s kind of a nerd, and a big part of his appeal when he first broke out was that he made geekdom more acceptable in the mainstream hip-hop space. You can see part of his nerdy nature in this shot of him rocking a Blade Runner T-shirt. Back in 2020, he tweeted out a video of 2017’s Blade Runner 2049, revealing himself as a big fan of the franchise, saying: “I WATCH BLADERUNNER ON REPEAT.” Ye can also be spotted wearing a Taxi Driver tee while holding thighs down on a mixing board in jeen-yuhs. 

Rare Adidas 

Ye was a big Adidas fan long before he teamed up with them to release a shoe. Here, he rocks the Adidas Marathon TR during a special photo shoot. He pairs the kicks with a crispy black tee and his Roc-A-Fella chain in hand, crystallizing a solid fit in the Ye fashion continuum. 

Lacoste polos 

In the early 2000s, Ye dove into his Lacoste bag, rocking a variety of different colored polos over the years. You can see him rock a red one and an orange one at different points in jeen-yuhs, wearing them with either a bucket hat or a snapback.

Preppy sweaters

In the early 2000s, Ye was in full backpack rapper mode and that meant rocking an array of preppy attire, with cozy sweaters like this one being a hallmark of Yeezy’s prep phase. 

Beanies 

If you watched the video for Cam’ron’s “Get ’Em Girls,” or if you saw him freestyle on BET’s Rap City, you know that early Ye was big on beanies. 

Roc-A-Fella chain 

After signing to Roc-A-Fella Records, Ye wore the Roc-A-Fella chain like a badge of honor. By 2007 or 2008, he was arguably bigger than the label itself, so you didn’t see it as much, but in the early ’00s, this was an essential part of Yeezy drip — a sign that he’d made his rap star dreams come true. 

Polo Bear T-shirts

Another example of Ye’s polo infatuation, this Polo Bear tee, as well as other shirts like it, were a staple of Yeezy Y2K fashion. Casual yet coated in the subtle whimsy of a cartoon bear, the look is emblematic of an artist who swerves between high fashion and surreality in all his work. Pairing playfulness with style, Ye straddled the line between street fashion and prep and, in the process, helped redefine both in a way that only he could. This was Ye in the early ’00s — the era of Fly2K.