From ‘College Dropout’ to ‘Donda’: A Look at Kanye West's Style Evolution

Image via Complex Original

When: 2004

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 sunglasses

By 2005, Kanye had commercial and critical success with The College Dropout and more money. 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

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

When: 2008

Key Pieces: Fitted grey suit, red heart pendant, Pastelle varsity jacket

With 808s & Heartbreak, Kanye took on a very specific look: grey suit, oversized sunglasses, red heart pendant, and a mullet. It was a more pared down look and a departure from the sometimes loud, streetwear looks he previously wore. When he wasn’t wearing the grey suit with a crisp white shirt, he donned closely cut denim jackets and trench coats, tuxedos with bowties, cumberbunds, and bomber jackets—during this era he was working on his line Pastelle, which never saw the light of day, but Kanye did wear the royal blue varsity jacket to an event and it’s now a grail. At this point, Kanye had worked with Marc Jacobs on a sneaker, but he still felt like he had something to prove to the fashion industry. This was also the time period when Kanye showed up to Paris Fashion Week with his friends and collaborators Virgil Abloh, Don C, Taz Arnold, Chris Julian, and Fonzworth Bentley. They couldn’t get the shows, but they went anyway. This moment was memorialized by street style photographer Tommy Ton and ended up being featured on an episode of South Park. Around this time is also when Kanye released his first sneaker, Air Yeezy, with Nike. He was inching his way into the fashion and sneaker space and setting a blueprint for those that came after him.—Aria Hughes

When: 2010

Key Pieces: That red Phillip Lim suit, a gold Horus chain, finely tailored suits to represent the Rosewood movement, and that beautiful Celine blouse

Kanye West has put on plenty of memorable outfits in his lifetime. It could be argued that few (if any) are as memorable as the bright red suit he wore to premiere “Runaway” to close out the 2010 MTV VMAs. It wasn’t just the suit though. It was the plethora of gold chains around his neck. It was the all-red Louis Vuitton Dons on his feet. It was the MPC drum machine positioned on a white pillar at the center of the stage. It was a big performance that set the tone for the rest My Beautiful Dark Twisted Fantasy chapter. The all-red ensembles would make appearances again with other accessories like a gigantic gold Horus chain in subsequent performances. The red and gold color palette even carried over to the album cover designed by George Condo. 

Kanye didn’t only wear a red suit following the album’s release. He also wore the now-famous Givenchy rottweiler T-shirt that would help propel him into his Watch the Throne era of leather kilts and all-black ensembles, python skin snapbacks by Don C, and of course he wore that amazing Celine blouse on stage at Coachella in 2011. We also can’t mention the MBDTF era without showing love to the Rosewood movement. The tailored black suits and bow ties became a uniform that Ye championed leading up to the album’s release. The mentality included behaviors like, “not cursing loud in public, pulling out chairs for your lady, opening up doors.” If you were going to behave like a sophisticated gentleman, you needed to dress the part too. “That’s Dior Homme, not Dior, homie.”—Mike DeStefano

When: 2013

Key Pieces: Yeezus merch, bomber jackets, distressed denim, and diamond-encrusted Margiela masks

You know all that artist merch that comes out nowadays? It’s safe to say that the success of Kanye West’s Yeezus tour merch were the catalyst for that. Artist Wes Lang, known for his work with heavy metal legends Metallica, created the artwork on the T-shirts that included skeletons kneeling in prayer or dressed like the Grim Reaper. The merch line also provided the infamous olive green bomber with a Confederate flag on the sleeve that aged rather terribly. The classic military jacket, sans flag, did become a hot commodity around the time in large part to Kanye’s influence though. Kanye matched the rebellious sound of the album by introducing things like distressed denim and droopy, faded T-shirts to his wardrobe around this time. 

On stage for the Yeezus tour, he provided fans with another signature look by performing in diamond-covered face covering made by Maison Margiela. He was setting footwear trends during the Yeezus era too. No, it wasn’t all of his Adidas Yeezys yet. Instead he had people coveting expensive designer shoes like the Balenciaga Arena and Visvim FBT. Sooner or later, his entire grunge aesthetic was populating fast fashion stores like H&M and PacSun. The latter even stocked its own exclusive Yeezus merch at the time. The phrase “cultural reset” is incredibly cliche, but if you look at the direction that fashion took in the years that followed, it isn’t entirely untrue in this case.—Mike DeStefano

When: 2016

Key Pieces: TLOP merch, Adidas Yeezys, Adidas track pants, and earth-toned sportswear

Aside from his trendsetting and ever changing wardrobe, it was always clear that Kanye West wanted to design too. Throughout his career there were independent attempts, namely an anticipated Pastelle brand that never made it to market and a critically panned DW by Kanye West women’s runway show at Paris Fashion Week in 2011. His collaborative work with Louis Vuitton, Nike, and Adidas was celebrated and coveted. But by 2016, it seemed like Kanye had finally found his footing as a designer with his Yeezy clothing line. Drapey, earth-toned sportswear became its signature with pieces like roomy T-shirts, bombers, and women’s bodysuits dominating the first two collections. Yeezy Season 3 was the real spectacle though. Kanye packed Madison Square Garden on a February afternoon in 2011 to experience his latest work. For the non-traditional show format models stood on large cubes at the center of the arena. Among them, Young Thug sitting in a bright yellow fur-lined coat, and a then-relatively unknown Lil Yachty in a red sweater to match his braids. Oh, Kanye debuted his new album The Life of Pablo and jumped around in excitement with friends like Kid Cudi and Travis Scott too. 

And we can’t forget the TLOP merch that came along with it. The maroon long sleeve with infrared lettering that Ye wore to the Yeezy Season 3 show and airbrush-inspired tribute to his mother Donda and Robert Kardashian are probably the most memorable at this point. They were far from the only items, though. Pop-ups across the country were selling variations on the Old English-lettered “I Feel Like…” merch. It eventually trickled into mall stores and became overkill, but it was another testament to Kanye’s massive influence. Throughout the run, Kanye was usually seen rocking it himself, which only made it more coveted. The designer pieces were still in the mix sometimes, but for the most part you could expect to see him in sweatpants, black hoodies, TLOP merch, and an endless rotation of his Adidas Yeezy sneakers. It was an easily inimitable uniform. And plenty of his fans followed suit.—Mike DeStefano

When: 2018 

Key Pieces: Dad hats, trippy streetwear, and basics

One of the most difficult moments of Kanye West’s career came right around the release of Ye. After Kanye West was hospitalized due to a psychiatric emergency, the rapper began spending more time between his quiet homes in Calabasas, California and Cody, Wyoming. This was when we saw Kanye reel back a little and wear calmer garments. Pieces like Brain Dead T-shirts or sweatpants with comfy Yeezy Adidas sneakers. He frequently wre dad hats with nothing but a simple button-up shirt or a zip-up hoodie. When Kanye did show up to large public events, like Virgil Abloh’s first Louis Vuitton show or the release party for Ye, he brightened up his fits with bold graphic long sleeves that featured unique art with a DIY aesthetic. But even in the winter, when folks really start dressing, Kanye kept it minimal. He would come out wearing something like a shearling Yeezy coat with just a basic black sweatshirt, jeans, and a pair of white sneakers. Although Kanye didn’t exactly wear his most memorable outfits during this period, and is likely more remembered for donning a red MAGA hat than anything, he managed to still develop a style that was uniquely his own.—Lei Takanashi

When: 2020

Key Pieces: Robes, tunics, workwear, denim, and blue Yeezy Gap “Perfect” hoodies. 

Now ignoring that ridiculous ‘Vision 2020’ merch and his faith-based campaign to run for POTUS, Kanye West’s style during this era was mostly calm and collected to say the least. During his Jesus Is King performances, Kanye wore dyed oversized T-shirts that looked more like tunics a monk would wear at some monastery in the mountains. And at his performances for the opera that accompanied Jesus Is King, titled Mary, we even saw Kanye take his religious-inspired looks to a whole new level by painting his face silver and donning a long silver robe. This was definitely another odd period for Ye when it comes to the evolution of his style. Perhaps one of the strangest looks he put on during this time was a natural extension of the Alyx chest packs he used to wear, since he suddenly held a presidential campaign rally while in a bulletproof vest. But nevertheless, some of Kanye’s more memorable looks from this time included outfits that showed his deep appreciation for denim and workwear. For example, Kanye showed up to the 2020 Met Gala wearing Dickie’s from head to toe and also frequently wore denim from Tremaine Emory’s Denim Tears x Levi’s collaboration. He also began teasing the Yeezy Gap line by frequently donning a blue “Perfect” hoodie, which may have no pockets but somehow always looked good on Kanye.—Lei Takanashi

When: 2021

Key Pieces: Custom face masks, Yeezy Gap Round Jackets, and Balenciaga Crocs

One of the best parts of any Kanye West album rollout is seeing the wardrobe that will come along with it. For his most recent project Donda, he once again created a new signature style that fans will always be able to connect to the album. One of the standout items this time around: his face masks. It’s clear he loved the Margiela masks from his Yeezus tour because he has decided to revisit the concept. Some of them have been full face coverings with imagery like growling panthers similar to the one he was spotted in at the Balenciaga Fall 2021 couture show earlier this month. Other iterations have featured eye openings and were crafted using repurposed vintage T-shirts. Yeezy designer Greg Ross is reportedly behind the creation. His Yeezy Gap creations have take center stage as well. During the first Donda listening session in Atlanta, he wandered around a desolate Mercedes-Benz Stadium floor in a bright red version of the puffy Round Jacket. The blue and black colorways were spotted on him during a handful of appearances too. But his increased work with Demna’s Balenciaga may be the major development from the Donda era. Not only did the Georgian designer help craft the imagery of second and third Donda listening sessions and design merch for both events, Ye became an unofficial ambassador for the brand along the way. Spiked jackets, dad caps covered in white flames, and leather jackets were all highlighted in Ye’s stealthy all-black attire. And who could forget his signature pair of Balenciaga x Crocs boots that he seemed to not be able to take off. The partnership culminated in the announcement of an official Ye x Demna partnership, Yeezy Gap Engineered By Balenciaga, back in January. With Donda 2 reportedly around the corner, don’t expect Demna’s influence on Ye’s aesthetic to fade any time soon either. —Mike DeStefano