Album Era: The College Dropout

In early 2004, Kanye was best known as a producer. In fact, when he took to the stage at Richmond Convention Center in January of 2004, his debut album, The College Dropout, hadn’t dropped yet. At the time, Kanye was putting the finishing touches not on the album, which would officially debut in February, but on the rollout, doing promotional appearances and filming videos. When he appeared at Richmond Convention Center, for Roc-A-Fella’s Weekend Jump Off, he had apparently been filming clips earlier in the day.

But we digress.

What Kanye wore on that day was emblematic of the producer-turned-rapper, who was framing his debut album—and, really, his debut triumvirate—through the lens of a collegiate journey: a Polo Ralph Lauren intarsia knit Polo Bear sweater, with a gold Roc-A-Fella chain and a matching watch. Kanye’s love for Polo is by now well-documented, but, at the time, it set the stage for the prep-adjacent Kanye that took the hip-hop world by storm in the mid-aughts.

Album Era: The College Dropout / Late Registration

It would be a little disingenuous to say that early 2005 was exclusively part of either The College Dropout or Late Registration eras. At the time of the 2005 Grammys, Kanye was between those two albums, basking in the after-glow of *The College Dropout’s success and preparing to release Late Registration. Kanye took home Grammys for Best Rap Song and Best Rap Album, in addition to performing “Jesus Walks” and being nominated a whopping ten times in 2005.

Quite famously, he took to the stage in an all-white suit to accept his awards, but it was what he wore to a pre-Grammy brunch that’s worth highlighting.

At the Artist Empowerment Coalition, Kanye did his best Cam’ron impression, rocking an all-pink ensemble composed of a velvety suit with strong lapels—à la Tom Ford, as CR Fashion Book pointed out—,a matching turtleneck and tinted sunglasses. It was a departure from Kanye’s more unruly takes on tailoring—his penchant for wearing his shirts untucked or undone with an aloof necktie—or more casual getups. More interesting, perhaps, is that it underscores Kanye’s long standing love of monochromatic looks.

Album Era: Late Registration

Kanye’s next big ‘fit saw the aviator silhouette he wore to the pre-Grammy brunch return, albeit with a more classic, non-pink tint. By the time the VH1 Hip-Hop Honors rolled around in September 2005, Late Registration had dropped and Kanye, now one of the biggest names in hip-hop, took to the stage to perform—twice, actually.

For one of those performances, Kanye donned the aforementioned glasses, with an untucked white shirt layered under a brown and beige argyle sweater with pink accents, courtesy of Fred Perry. As with the Polo Bear sweater, the argyle was a nod to the edgy prep vibe that Kanye leaned heavily into when promoting his first three albums. But the mix of colors—brown and pink—would also become synonymous with so-called Old Kanye. Not only had Kanye worn pink before (see above), but that combination would feature in his footwear collaboration with Louis Vuitton, as well as on his Bapestas and, later, on Air Yeezys.

Album Era: 808s & Heartbreak

After Kanye’s third album, Graduation, he dabbled in clubwear for the bulk of his 2008 “Glow In The Dark Tour” and most of that year’s award shows—big sunglasses, fox tails, hoodies with LEDs. But as he was ramping up to release 808s & Heartbreak, he began to lean more heavily into polished, formal tailoring, sowing the first seeds of what would become the Rosewood Movement.

808s & Heartbreak’s brooding, yet minimalist, sound was influenced by Kanye’s life in the late-aughts: the passing of his mother, his split with fiancée Alexis Phifer, and his first real struggles with the spotlight that his fame brought.

The signature 808s & Heartbreak look was arguably coined at Thakoon’s Spring/Summer 2009 Runway Show, in September 2008, just a few months before Kanye’s most divisive album was released. The grey suit, with a faint check, suspenders, buttoned up shirt—worn sans tie—and glasses would become Kanye’s go-to look for 808s & Heartbreak, most notably for the press shots that circulated and during some performances. At the Thakoon show, he wore boat shoes, which, again, would influence his collaboration with Louis Vuitton a year later.

Album Era: My Beautiful Dark Twisted Fantasy

If you were to pick one album from Kanye West’s career, you’d pick My Beautiful Dark Twisted Fantasy, an objectively perfect album. And if you were to pick one song from the album, you’d pick “Runaway”—arguably perfect, too. If you were to pick one performance from the turn of the decade, you’d pick… well, actually, Kanye is a serially great performer, so perhaps you’d pick Coachella, but his performance of “Runaway” at the 2010 VMAs would certainly be on the shortlist.

The year prior, Kanye infamously interrupted Taylor Swift at the VMAs, which ended up kickstarting his efforts to polish his image, taking the 808s & Heartbreak aesthetic and turning it into the Rosewood Movement. Long story short: the 2010 VMAs were a big moment for Kanye, both professionally and personally. Oh, and he and Amber Rose had split only a few months prior to his performance.

He didn’t disappoint. The performance is remembered as a Kanye masterstroke, putting his showmanship and aesthetic sensibilities at the fore, with his red shawl collar tuxedo, black scoop neck T-shirt, gold chains and a pair of his Louis Vuitton Dons in, you guessed it, red. Like with the beige brown and pink argyle sweater from the VH1 Hip-Hop Honors, the red would foreshadow a future Air Yeezy 2 colorway.

Album Era: My Beautiful Dark Twisted Fantasy / Watch The Throne

Kanye’s dalliance with the runway coincided with the birth of the Watch The Throne project. Yes he had attended runway shows and released a collaboration with Louis Vuitton—not to mention the whole Pastelle project—before, but Watch The Throne saw Kanye take a further step into the fashion world. His friendship with Riccardo Tisci—who designed the album art for Watch The Throne, as well as some of the merch—saw him spend a considerable amount of time decked out in Givenchy.

One such instance? Taking a front row seat at Givenchy’s Fall/Winter 2011 show, where he sported Tisci’s now-famous Rottweiler-emblazoned T-shirt with black leather pants, black high top sneakers and a black bomber jacket. Not only did this offer the blueprint for Kanye’s relationship with the fashion world, but it’s arguably what allowed the Rottweiler design to become as famous as it did.

One could even argue that few—if any—‘Ye outfits were more influential than this one, in the grand scheme of things.

Album Era: My Beautiful Dark Twisted Fantasy / Watch The Throne

What’s the greatest Kanye outfit of all time? Easy. It’s what he wore on-stage when performing at Coachella, in the spring of 2011, just before Watch The Throne dropped—a performance The Hollywood Reporter dubbed one of the greatest hip-hop sets of all-time.

West’s red suit—from the 2010 VMAs—returned for part of the show, albeit without the scoop neck tee underneath. But you likely already know that’s not the outfit we’re referring to. No, what we’re talking about is, of course, the Phoebe Philo-era Céline Spring/Summer 2011 blouse, paired with faded denim, and worn gratuitously unbuttoned.

The blouse itself is a beautiful garment, but the way that Kanye wore it gave it new energy. But, what really turned heads at the time—keep in mind this was a decade ago—was that it was ostensibly a women’s piece. As people point out at the time, though, it’s not like you’d be able to tell just by looking at the shirt. But, still, it marked an important step for Kanye stylistically—and offered a hint that he wasn’t afraid of challenging gender norms in fashion, which would be cemented when he took to the stage in a leather kilt during the Watch The Throne Tour.

Today the Céline blouse in question is rightfully considered a collector’s item, fetching five figures on the second-hand market.

Album Era: Watch The Throne

While it may seem from his lyrics and sartorial choices at the time that Kanye had become a capital-F fashion-only kind of guy, he proved that he was also a man of the people when he took to the stage at the 2011 Victoria’s Secret Fashion Show wearing Versace x H&M. Performing with Jay-Z, the other half of Watch The Throne, Kanye wore the now-iconic Versace x H&M bomber jacket, a pair of leather pants and the Black/Pink colorway of his Nike Air Yeezy 2.

In addition to performing with Jay-Z, Kanye also performed “Stronger”, which he had been scheduled to perform at the Victoria’s Secret Fashion Show in 2007, before his mother passed away, leading to the cancellation of the performance.

Already arguably the standout piece from the collection, Kanye’s wearing of the Versace x H&M bomber turned the piece into a piece of hip-hop fashion lore, sending the resale price closer to $1000 than the original retail price.

Album Era: Yeezus

It was after Watch The Throne, as Kanye was beginning to work on Yeezus and beginning his relationship with Kim Kardashian, that he started spending a considerable amount of time in Paris—foreshadowed by a certain track on Watch The Throne and studio sessions in Parisian hotel rooms.

From a fashion standpoint, one could argue that this phase of Kanye’s career was the most interesting.

Case in point: showing up to the Céline Spring/Summer 2014 show—and later stepping out of his classic matte black Porsche Panamera, matte black MacBook Pro under his arm—wearing a long Rick Owens DRKSHDW parka, with a tie-dye T-shirt layered underneath, a turquoise beaded necklace, distressed denim and Visvim Shaman-Folk FBTs. Not only did it portend the dark, drapey aesthetic that would come to define the Yeezus era, but it also marked an interesting development in terms of Kanye’s—and hip-hop writ large—rapprochement with the fashion world, swapping classic luxe brands like Gucci and Louis Vuitton for more directional labels like DRKSHDW, Margiela, or Visvim.

Album Era: Yeezus

This segues quite nicely into what Kanye wore during the Yeezus Tour, held throughout both 2013 and 2014. From a personal standpoint, the Yeezus Tour marked the beginning of a chaotic part of Kanye’s life. From the off, the tour encountered obstacles, after a car crash damaged stage elements beyond repair, causing significant delays and cancellations of some tour stops. Kanye also spent considerable time during each show ranting about various topics, ranging from the death of his mother to the demise of his partnership with Nike.

On the other hand, Yeezus arguably marked the peak of Kanye’s creativity. It was during this time that his desire for more creative freedom put him at odds with Nike. It was also during this era that he started working with A.P.C. And that’s to say nothing of the immensely popular—and controversial—Yeezus merch designed with the help of Jerry Lorenzo.

The standout, though, was what Kanye took to the stage in throughout the Yeezus Tour: an array of outfits designed in collaboration with Maison Margiela that were eery, dark and ethereal. Of course what people best remember from them are the series of face masks, especially the crystal covered iteration worn during the Atlantic City show. Many of these outfits were famously documented by street style photographer-turned-designer Tommy Ton.

Album Era: The Life of Pablo

In case it wasn’t yet obvious, Kanye has a penchant for showing up in style when it comes to awards shows—especially those where he’s giving a performance. In 2015, Kanye was on a bit of a musical hiatus. He and Kim Kardashian had married a little under a year before the 2015 Grammys, and the years between Yeezus and The Life of Pablo marked the period when Kanye and adidas entered into their fruitful partnership. Knowing how much Kanye cared about creating a footwear and fashion empire, it wasn’t a surprise to see his music take a back seat.

Kanye used the Grammys stage to show off the new Yeezy Boost 750, which released throughout February 2015, at retailers across the world. He also took to the stage in a burgundy velvety sweat suit, which many mistakenly assumed was from his upcoming Yeezy Season 1, set to be shown a few days later. It wasn’t though, it was Haider Ackermann. It did, however, offer a glimpse at the blueprint that Kanye was going to emulate for Yeezy: ultra-luxe casualwear.

While The Life of Pablo was still a ways away, both the on-stage sound, “Only One” and the look are decidedly part of the The Life Of Pablo era.

Album Era: The Life of Pablo

Half a decade before Drake was Toosie Sliding in it, Kanye was establishing the blueprint for rappers wearing Raf Simons’ Riot Riot Riot bomber jacket.

Again, in the spring of 2015, ’Ye was between Yeezus and The Life of Pablo, working on new music, but devoting a considerable amount of his attention to his fashion interests. And, as we saw during the Yeezus Tour, that meant that Kanye was pushing the boundaries of rap-adjacent fashion beyond the classic monogram brands.

Here he was, attending the Dries Van Noten Fall/Winter 2015 show—a designer that’s celebrated in the fashion world but, let’s be honest, not exactly a household name—wearing an archival Raf Simons bomber, decked out in woodland camouflage and adorned with David Bowie and Bauhaus patches, with a sage green hoodie underneath, simple black denim and chocolate brown Yeezy 950s.

The Riot Riot Riot bomber was already revered in archival circles, but there’s no doubt that Kanye’s co-sign added a few thousand to the resale prices it would eventually fetch—famously selling for $47,000 on Grailed a few years ago (with the bomber serving as a regular addition in our roundups of the most high-profile, expensive sales year-after-year).

Album Era: Ye

By August of 2018, when 2 Chainz married his longtime partner Kesha Ward, Kanye had not only released The Life of Pablo, but also Ye, the secretive project crafted in Wyoming, where he had retreated to after being hospitalized for a “psychiatric emergency” during the Saint Pablo Tour. He had also grown the Yeezy brand into a force to be reckoned with in the fashion-meets-streetwear realm.

Going bare-chested in a sage-ish cream-colored Louis Vuitton double-breasted suit was already a bold choice, but pairing that with similarly-colored socks and Yeezy slides was definitely a choice, as they say. But we’re buying the lede here, what people really talked about was that Kanye’s slides looked as though they were two or three or four sizes too small, with his heel perched precariously over the edge. It sparked a debate, with Kanye, himself, weighing in and declaring that he was wearing his sandals, “the Japanese way.”

Regardless, we can report it was a momentous ‘fit.

Album Era: Jesus Is King

By 2019, Kanye’s religious rebirth was in full swing and he was working on Jesus Is King. Ironically, the Met Gala’s 2018 theme was rooted in religion, which would have suited 2019 ’Ye. 2019’s theme, however, was Camp.

Kanye did not disappoint, turning up to one of the most over-the-top fashion events in… a $50 Dickies Eisenhower Jacket, a pair of black pants and Yeezy Season 4 combat boots. Turning up to one of the most over-the-top fashion events in Dickies—a colossal flex, but also incredibly on point for the theme. Plus, the juxtaposition of him standing next to a Thierry Mugler-clad Kim Kardashian was striking. It also may have marked the beginning of the end for KimYe, the first crack in the armor of their celebrity marriage—who can say for sure?

Zooming out, though, the 2019 Met Gala is similar to the 2011 Victoria’s Secret Fashion Show in that it showed a more populist side of Kanye’s fashion sense. While workwear is something that’s effectively outside the cycle of what’s trending (or not), it’s clear that Kanye’s choice to wear Dickies from head to toe was going to help spur the sales of one of America’s hardest-working (and, financially, most practical) pieces of clothing.

Album Era: Jesus Is King

The Oscars were one of the last big events before COVID-19 struck. Jesus Is King had dropped to mixed reviews and one had the feeling that Kanye was now less of a rapper and more of a producer—both in terms of music and fashion.

When Kanye showed up to Vanity Fair’s Oscars after party, it wasn’t necessarily a shock to see him decked out in black leather. After all, he was someone who had helped popularize leather pants in the early-to-mid 2010s. He wore an all-Dunhill ensemble, composed of the single button double-breasted jacket —though also referred to as a wrap blazer—and matching pants, with sand suede boots.

Wait—Kanye in Dunhill? Dunhill, the very traditional British menswear brand? Yup. Apparently he became enamored with that particular Dunhill silhouette on the set of his GQ cover shoot and specifically requested the version he wore to the Oscars after party.

The lesson is that there are always brands outside one’s comfort zone that are worth taking a look at—you never know what you’ll find.