Album(s): The College Dropout (2004), Late Registration (2005), Graduation (2007)

While Kanye West first emerged in the late-‘90s and early-2000s as a producer—first for emerging Chicago artists and, later, as an in-house producer for Roc-A-Fella Records—he had always wanted to be a rapper. West had even lobbied his mother, Donda, to book studio time for him at the age of 13.

So, even as West helped craft Jay-Z’s iconic Blueprint in 2001, he wanted Roc-A-Fella to sign him as an artist, rather than as a producer. The label didn’t see Kanye as a rapper and begrudgingly gave him an artist deal to keep him from defecting to a competitor. Still, Roc-A-Fella remained unconvinced about his ability to put out a successful album. After getting into a serious car accident in 2002, West recorded “Through The Wire”, which ultimately paved the way for his first album, The College Dropout.

Predictably, the shift from being behind the boards to being behind the mic led to an increasingly public profile for Kanye. Before The College Dropout dropped, West was voicing his desire to be “the best-dressed rapper in the game,” while proudly proclaiming that, “he really liked clothes.” Interestingly, he did so while wearing a pair of adidas Superstars.

There’s always been an interesting relationship between rappers and fashion, with new, crisp, expensive clothes equated with wealth, success and swagger—that inimitable, impossible-to-define but all-important detail.

In some cases that amounted to outright braggadocio—never wearing the same pair of Air Force 1s twice, for example. Naturally, Kanye approached it differently.

Those he had been producing beats for were wearing billowing denim, the latest Nike sneakers, and sportswear—be it in the form of fitted caps, varsity jackets or jerseys. Kanye, on the other hand, announced himself to the world as a rapper while wearing Polo—from the iconic Polo Bear to polos to dress shirts—argyle sweaters, rugbys, and backpacks. His 2004 appearance on Sessions@AOL alongside Twista perfectly underscores the difference in Kanye’s fashion sensibilities and those of his contemporaries. Even his more formal outfits bucked trends in terms of what rappers were wearing. Kanye was comfortable in pink velvet jackets, turtlenecks, designer frames and slim cuts.

What Kanye was pioneering was prep-rap—an aesthetic that was latter embraced by Pharrell Williams in the late 2000s and early 2010s. One could even argue that Kanye’s prep look helped spawn the generation of prep-adjacent college rappers that emerged in the five-to-10 years after College Dropout and Late Registration. Nike took note of Kanye’s unique style as early as College Dropout, offering West a unique size 12 Air Max 180 that featured color blocking, leopard print on the rear and the Dropout Bear on the tongue.

It was a harbinger of things to come.

Rumor has it that the seeds for Pastelle were first planted circa 2006, and the Nike Air Max 180 likely galvanized Kanye in his belief that his unique aesthetic was something he could not only market but repackage and sell to the masses in the form of clothing and sneakers. Quietly, he began assembling a team of creatives—led Virgil Abloh, Don “Don C” Crawley, Willo Perron, and Matt George—who would further Kanye’s vision for Pastelle.

In 2006 and 2007, as Kanye was preparing to release Graduation, his style slowly shifted. In the year between Late Registration and Graduation, he dressed as a mogul might, with a particular affinity for white jackets and half-buttoned shirts. This may have been one of the rare instances where Kanye was trying to emulate one of his contemporaries—Diddy—rather than follow his own path.

On the whole, though it was part of a bigger shift that saw Kanye’s personal style evolve to align with an increasingly big profile and persona. His chains got bigger—as did the designer logos on his T-shirts. West’s presence was growing, too, something reflected in a limited-edition Dropout Bear-branded Bapesta collaboration that many collectors consider to be an ultimate Kanye West grail—high praise considering his now-prolific output.

As an album, Graduation had a more club-ready feel, especially on tracks like “Stronger”. Aesthetically, Kanye embraced this, with the subsequent “Glow In The Dark Tour”of 2008, and opting for club culture-inspired pieces as promotion for the album ramped up. He’d wear Takashi Murakami x Louis Vuitton accessories, multicolored BAPE and bold graphic pieces.

Sunglasses became a central tenet of Kanye’s style at this time—remember shutter shades from “Stronger” and the aforementioned “Glow In The Dark Tour”?—and in 2007, he approached the recently-launched eyewear brand Retrosuperfuture, of which he was a big fan. West and Retrosuperfuture founder Daniel Beckerman would go to have a mutually beneficial relationship, with the former giving Retrosuperfuture incredible visibility, while the latter became one of West’s consiglieri for the enigmatic Pastelle project.

Album(s): 808s & Heartbreak (2008)

808s & Heartbreak is one of Kanye’s more divisive albums. Released in November 2008, shortly after the Graduation-heavy “Glow In The Dark Tour” drew to a close, 808s & Heartbreak represents a massive break from so-called collegiate Kanye. His sound is brooding, introspective and heavily auto-tuned—as was the trend at the time (ultimately one he helped set across the industry). Inarguably, it was different and, arguably, it paved the way for the kind of rap that Drake became a superstar making. 808s & Heartbreak was the result of creative experimentation and while West was experimenting musically, he was also beginning to experiment more seriously with fashion.

Towards the tail end of the “Glow In The Dark Tour”, in the fall of 2008, Kanye began talking about Pastelle more openly, penning blog posts about it on the now-defunct “KanYeUniverseCity”, and wearing samples to the American Music Awards and the Dior Homme Spring/Summer 2009 runway show. Pastelle was the apple of West’s creative eye; he’d spend hours tinkering with designs and his dispatched creatives—which included the aforementioned creative roster, but also a young Kim Jones—would send him various ideas and designs for new pieces. Pastelle was supposed to be available for purchase in early-2009, but it’s well-known today that Pastelle would never see the light of day. Complex’s Karizza Sanchez has documented what could have been and what kept Pastelle from becoming reality in incredible detail. Suffice to say, though, that as Kanye was preparing to release 808s & Heartbreak, there was incredible hype for Pastelle, which was positioned to be an elevated streetwear brand.

This, despite the fact that Kanye was back to experimenting with a more classic menswear look as 808s & Heartbreak released. In retrospect, the suits, sharp buttoned-up dress shirts, scarves and Louis Vuitton backpacks were early hints of what was to come with the Rosewood Movement. Sure, the polos may have been BAPE, but the overarching aesthetic was a unique blend of prep, Scandinavian minimalism and dandyism.

Throughout 2008, Kanye’s style oscillated between that unique breed of minimalist tailoring and elevated streetwear, something which was reflected in West’s non-Pastelle fashion projects. On the heels of the aforementioned limited-edition Air Max 180, 2009 saw Nike tap Kanye West for what was, at the time, the first ever signature shoe given to a non-athlete. The Nike Air Yeezy, which released during Spring/Summer 2009, was designed throughout 2007 and 2008 by West, Nike creative director Mark Smith and Nathan VanHook. An instant sell-out, the shoes were available in three colorways—Blink, Zen Grey, and Net Tan—and quickly became one of the most coveted sneakers in the resale market.

Nothing better illustrates Kanye’s duality in that specific moment than the fact that while working on the Air Yeezy, he was designing a footwear collection with Louis Vuitton, too. One foot in the luxury world, one foot in streetwear.

Kanye’s affinity for Louis Vuitton was, by 2009, well-documented. As early as 2004, West was referring to himself as the “Louis Vuitton Don” and had worn the Parisian house’s monogram and damier pattern on numerous occasions. In June 2008, he announced that he was working with Louis Vuitton, then under the creative directorship of Marc Jacobs. In October, he claimed the design process was advancing well and that the shoes were looking good. "Who do you know with two thumbs and their own Louis shoe?", Kanye asked in early 2009, with the shoes stacked on the table behind him. One year after the original announcement, in July, 2009, the six shoe collection finally released.

Predictably, the Don, Jasper and Hudson did well, commercially. In the decade-plus since, they have become among the most sought-after shoes on the resale market, with some models fetching up to $20,000.

However, it’s not just the commercial success and resale mania that make Kanye’s 2009 Louis Vuitton collaboration noteworthy. Of course, it set the stage for his own future interest in working with the likes of Fendi and A.P.C. It was also truly trailblazing. Pharrell had previously collaborated with Louis Vuitton—but it was on a range of accessories. Outside of that, luxury fashion houses had traditionally turned to visual artists—like Takashi Murakami, a Marc Jacobs favorite—for collaborations. Kanye played a vital role in making collaborations between establishment luxury fashion and creative cultural figures possible. Many have argued that without Kanye, Virgil Abloh wouldn’t be at Louis Vuitton, which is very likely true—not just because of the personal connection, but because of the cultural shift that Kanye helped start.

No overview of Kanye’s experimental years—and his foray into the “capital-F” fashion world—would be complete without mentioning that Tommy Ton photo. In January, 2009, Kanye attended the Comme des Garçons runway show, alongside Chris Julian, Taz Arnold, Fonzworth Bentley, Don C, and Virgil Abloh. Canadian street style photographer Tommy Ton captured their unique looks, which fit more with West’s Graduation-era clubwear-meets-prepwear look than his more refined 808s & Heartbreak style: Goyard trunk, his Louis Vuitton sneakers, a Black Watch tartan coat, raw denim jeans—and that’s just Kanye.“This was actually before street style had become such a phenomenon and you could really see how much Kanye loved fashion and clothes,” Ton explained to Vogue.

Such was Kanye’s love for fashion and commitment to make it in the industry that, even with a Louis Vuitton forwear collection and signature Nike sneaker to his name, he arranged to intern for Fendi in 2009. In a 2013 interview with Zane Lowe, West claims that it was he and Virgil Abloh who introduced the idea of leather jogging pants while at Fendi, a trend that would eventually take hold in 2011-2012. More importantly, though, it was at Fendi that industry power brokers first took note of West and Abloh—another example of how West’s fashion focus around the turn of the decade is still impactful.

Album(s): My Beautiful Dark Twisted Fantasy (2010)

Released in 2010, My Beautiful Dark Twisted Fantasy is widely considered to be Kanye West’s magnum opus—proof to critics and fans and himself that he could create a perfect album. While Kanye had a number of non-musical projects in previous years—the Louis Vuitton collaboration, Pastelle, the Air Yeezy—he was laser-focused on My Beautiful Dark Twisted Fantasy in 2010.

Still, West’s personal style evolved around the time he was working on My Beautiful Dark Twisted Fantasy—and while it reflected the sound of the album, it was more a function of his behavior. When he infamously interrupted Taylor Swift at the VMAs, in 2009, he was wearing Balmain biker denim and a shortsleeved leather shirt; it was a fitting outfit for the occasion, something which gave off a carefree, luxurious, bad boy vibe. From that point on, though, Kanye—and his entourage—made a conscious effort to mature their image.

The minimalist tailoring that Kanye had experimented with in 2008, for 808s & Heartbreak, was the jumping off point for what came to be known as the “Rosewood Movement.” In a broader sense, Kanye made an effort to clean up his image, by being less confrontational, avoiding cursing, and, stylistically, by favoring designer tailoring.

While the red shawl lapel tuxedo that he wore when debuting “Runaway” at the 2010 VMAs is what people tend to remember, or the white smoking jacket from the “Runaway” short film, the entire My Beautiful Dark Twisted Fantasy year saw Kanye wearing scoop neck T-shirts under sports jackets. He’d wear turquoise blazers to the studio and appeared in i-D in outfits fit for power lunches on a yacht docked off Cannes. Of course, in true Kanyesian form, there was a counterweight to that: a few months before the VMAs and the i-D spread, he had performed at the BET Awards in a red shawl lapel suit—sans shirt and with the addition of a comedically massive gold chain.

Is it a coincidence that classic menswear and tailoring enjoyed a renaissance among younger men in the years that followed? Possibly. But it’s also likely to be a function of Kanye’s popularity and influence at the time. Consider that even Pusha-T—a fan of baggy streetwear if ever there was one—took to the stage in a pink smoking jacket for the 2010 “Runaway” performance.

Album(s): Watch The Throne (2011)

On the heels of My Beautiful Dark Twisted Fantasy, Kanye teamed up with Jay-Z for Watch The Throne, one of the most celebrated duet albums in recent memory. If My Beautiful Dark Twisted Fantasy was temporally aligned with the Rosewood Movement, then Watch The Throne saw Kanye emerge as a veritable fashion industry icon. In fact, 2011 may have been Kanye’s most prolific year in terms of influencing men’s fashion.

For one, it ushered in an era of close collaboration with then-Givenchy creative director Riccardo Tisci, who designed the Watch The Throne cover art, as well as a number of the tour merchandise pieces. It also marked a shift that saw Kanye move away from more traditional luxury menswear items—suits, monogrammed backpacks—and brands towards more fashion-forward pieces and labels.

It was on Watch The Throne that Kanye followed up references to Louis Vuitton and Gucci with a Margiela name drop; while the brand was well-known in 2011, it was not one that many rappers were referencing. Tisci had a particularly outsized influence on West, dressing him in a number of his Givenchy pieces, from leather pants and kilts to the now iconic Rottweiler-emblazoned T-shirts.

In that regard, Kanye’s influence is impossible to deny. Yes, Tisci may have been the one providing some of the pieces that Kanye wore, but it was Kanye that helped make them it items. Without Kanye, would Tisci’s Rottweiler design be as famous as it is today? Doubtful.

Undoubtedly, it was Kanye who paved the way for the rapprochement between hip-hop and high fashion.

Alongside Pharrell, Kanye helped normalize a bit of gender-fluidity in dressing, wearing the aforementioned kilts, but also a women’s blouse from Phoebe Philo-era Céline while performing at Coachella in 2011—arguably his most famous outfit. Here was the most popular rapper in the world wearing tight leather pants, plaid shirts and brands like Balmain, Maison Margiela and… Versace x H&M. Odd as that last one may be, it fit, aesthetically, with 2011 Kanye and all of the other brands and pieces that he was wearing.

Album(s): Yeezus (2013)

By 2013, Kanye was ready to release his next solo album, Yeezus, and he had gone even further down the fashion rabbit-hole. Visvim, far from a mainstream luxury brand, was among West’s more tame choices. He had traded mainstream designer sneakers for obscure Vans x WTAPS Sk8-His that were still sitting on shelves—but promptly sold out after paparazzi snaps emerged.

His Yeezus merch, designed with an important assist from Jerry Lorenzo and Wes Lang, was incredibly popular—but also incredibly controversial because of its use of the Confederate flag. Like Yeezus’ sound, the merch was confrontational and loud—obnoxious, even. Kanye, for his part, was increasingly dressing for confrontation, with designer garments inspired by military surplus. His color palette—once vibrant—now hinged on olive drab, grey and black; he wore bomber jackets, military parkas and heavily distressed denim. On stage, Kanye routinely wore head-to-toe Maison Martin Margiela, from bejewelled masks to oversized parkas to various iterations of the German Army Trainer.

It was a look that few—if any—in the mainstream understood.

But this being Kanye, he found a way to distill that almost chaotic military-inspired aesthetic into something more commercial through a 2013 collaboration with Jean Touitou’s Parisian label A.P.C. It offered a taste of what a finished Kanye West-designed clothing collection might resemble—and how it would perform (spoiler: incredibly well).

It wouldn’t be a stretch to argue that Kanye’s Yeezus-era look helped lay the foundation for the boom in archive culture. After all, many of the T-shirts riffed on vintage concert merchandise—something which Jerry Lorenzo also capitalized on with Fear of God—while the military-esque Margiela stage pieces and A.P.C. collection are aesthetically similar to many of the Helmut Lang and Raf Simons pieces that were central to many of the early online archive communities.

But let’s rewind to 2011, between Watch The Throne and Yeezus, for a second.

It was in September, 2011, that Kanye staged his first runway show, for an eponymous label’s Spring/Summer 2012 show. While the collection was widely panned and didn’t amount to much in the long term, it represents, in hindsight, an important stage in West’s fashion education. With Pastelle, he didn’t go beyond ideation. Then, he immersed himself further, with Fendi, Louis Vuitton, A.P.C. and Nike. With his eponymous line, he was one step closer to launching a brand that, in his eyes, did his vision justice, but he wasn’t quite there yet.

Yet he felt he was.

On the heels of the hugely successful two-part Nike Air Yeezy II release, that spanned 2012 and 2013, Kanye publicly declared that he was being unfairly treated by Nike. He wanted to do more, but Nike wouldn’t let him. He wanted royalties from the shoes, but Nike wouldn’t give them to him. So he left.

Shortly after, he took to a stage in Herzogenaurach and announced that he would be partnering with adidas. 18 months later, in February 2015, the first Yeezy Boost 750 was released, with the low-top Yeezy Boost 350 releasing in June of that year. adidas gave West the creative control and financial support he craved for his grandiose vision and, in exchange, he gave them an incredible platform. When he took the stage at the Billboard Music Awards, in 2015, wearing a triple white pair of Ultra Boosts, he helped launch the silhouette and the tech that would help adidas temporarily catch up with—and even overtake in terms of immediate cultural clout—Nike. Such was his influence on demand for all things Boost that shoes which were readily available before that performance, became almost impossible to come by.

Album(s): The Life of Pablo (2016)

Kanye’s burgeoning relationship with adidas acts as a bit of a buffer between “old” Kanye and the one we’ve known over the last half-decade—a distinction he, himself, opined on with “I Love Kanye”, off The Life of Pablo.

While Kanye toned down his style a bit on the heels of the Yeezus tour, he appeared to find the foundation for a lasting aesthetic—not just for himself, but for his Yeezy brand. The toned down color palette that Kanye had sported on his 2014 tour became a staple of his outfits from 2015 onwards, and he often stuck to monotone looks. If the clothes he had worn in 2013 and 2014 were rife with references to combat and confrontation, then those he wore—and designed—in 2015 and beyond seemed drawn for a post-conflict world.

When Kanye showed up to the 2015 Grammys and performed in a burgundy velour sweatsuit with his Yeezy 750s—he changed into a tuxedo after his performance and before mock-interrupting Beck—many wondered whether it was from his upcoming Yeezy Season 1, which was set to be shown a few days later. It wasn’t. It was Haider Ackermann, a designer West had worn as early as 2013 and was quite fond of. In the early Yeezy/post-Yeezus days, much of West’s wardrobe was Ackermann. The Colombian-born French designer was revered within the fashion industry—tipped, at various points in the late-2000s and early-2010s to take over for John Galliano at Dior, Martin Margiela at his eponymous Maison and Karl Lagerfeld at Chanel—but West’s affinity for his work catapulted the designer’s then-nascent menswear offering to new popularity.

His creations represented a sort of ultra-luxe, elevated evolution of what West had been wearing previously. They also appeared to be the blueprint for what West was striving to make with Yeezy.

From the very first presentation for Yeezy Season 1, in 2015, the brand’s overarching aesthetic has been a mix of Yeezus-era Kanye and Haider Ackermann-clad Kanye. Fans and critics alike likened the first garments to apocalypse wear and, frankly, the collection wouldn’t have looked out of place had it been used for The Matrix.

Yeezy, hasn’t actually evolved much aesthetically. Yes, the pieces have changed, and many of the garments have become increasingly technical; but the underlying aesthetic remains rooted in a seemingly dystopian vision for the future. On the whole, it fit with West’s personal aesthetic, and, in the latter stages of 2015 and throughout 2016, his outfits became a mixture of Haider Ackermann, military surplus and Yeezy—often paired with the latest Yeezy sneakers or military-style boots. The result is a fashion-forward take on many streetwear and sportswear staples: loose-fitting T-shirts and sweatpants, baggy jackets, vests and color-coordinated layering.

Kanye’s stylistic turn played an important—if not singularly vital—role in the emergence of the athleisure movement circa 2016-2017. That’s partly tied to what he was doing with Yeezy, but, when Kanye took to the stage at the BRIT Awards in 2015, flanked by hundreds of black-clad grime figures, he didn’t just help introduce grime, as a musical style, to a North American audience, he introduced the grime aesthetic, too. He helped push the tracksuit and sneakers-heavy fashion that would become the norm for at least a few years—one which Yeezy, as a brand, was perfectly placed to capitalize on.

This era was also an explosion for Kanye West “merch”. Designed with help from Cali Thornhill-Dewitt, a series of city-to-city drops practically predates (if you really think about it) the tidal wave of musician-adjacent merch that would follow in years to come. Today, this is epitomized, as a singular example, by the slew of products dropped by Travis Scott. Beginning as a badge of insider status and blossoming into several public drops—it was almost impossible to escape Pablo-related merch—whether the wearer “Felt Like Pablo” or “Felt Like Kobe”.

That music was no longer Kanye’s focus wasn’t up for debate by the time The Life of Pablo dropped. For one, the album was a seemingly never-ending, on-again-off-again project that Kanye kept tinkering with, even after it officially released on streaming platforms in late 2016. Secondly, it was overtly tied to Kanye’s fashion ventures. “Wolves”, a song with immense potential that Kanye never quite nailed down, debuted at a fashion show. More to that point, it seemed apparent that Kanye was using his musical prowess and fame to boost his fashion endeavour, by debuting The Life of Pablo, off his laptop, alongside the Yeezy Season 3 presentation at a packed Madison Square Garden in 2016.

Album(s): Ye (2018), Jesus is King (2019)

A few months later, West was hospitalized for a “psychiatric emergency” after abruptly cancelling his tour. While he has made public appearances since then—notably at Trump Tower and the White House—West has spent much of the last three years splitting his time between Calabasas and his ranch in Cody, Wyoming.

When he has appeared in public, streetwear staples, like track pants, T-shirts, hoodies and crewnecks, have remained constants in his rotation, but rather than have a singular style for this current iteration of Kanye—as we’ve seen in the past—it seems as though he’s riffing through his accumulated aesthetics: a Virgil Abloh for Louis Vuitton suit, leather pants and jackets, a mismatched Canadian tuxedo, Carhartt, a double-breasted aqua overcoat, an olive green fishtail parka layered over a denim jacket. He even wore a full on Dickies jacket and pants to the “Oscars of Fashion”, the Met Gala, in 2019. What’s interesting is that both The Life of Pablo and Ye, released in 2018, contain the same kind of blend of his musical styles from over the years.

Still, despite West’s scaled-back public persona, penchant for controversy, and music—Ye, Jesus Is King—that’s less popular than his previous work, the Yeezy empire has grown, largely unabated. Demand for the clothes has slowed down since West first introduced Season 1, but as he showed in Paris, in March, 2020, he’s still intent on pushing the brand forward into weird, uncomfortable territory. The Yeezy empire is instead buttressed by sneaker sales—despite the fact that the shoes might not sell out as instantaneously as before, there’s no denying they’re incredibly successful commercially.

West’s pivot into the gospel scene reignited conversation (and even controversy) around his personal and political views. In terms of the artist’s personal style, this has ultimately boiled down to his “Sunday Service” series, creating merch with a biblical bent; with monochromatic, robe-like outfits an on-stage regular, its an interesting compliment to his relatively blue-collar wardrobe choices.

There’s no doubting his musical genius, just as there’s no doubting his outsized impact on trends over the last fifteen years. But clearly, his mind is elsewhere right now. Even as Yeezy continues to churn out collections—and with a 10-year partnership with Gap on the table—it’s clear that Kanye’s vision has turned towards other things. He’s posting foam construction creations, vehicles, and ideas for new living spaces.

It’s odd to look over the entirety of Kanye’s style evolution. For much of his career, there are clear links between how he was presenting and dressing himself, and how his music sounded. Now, things seem convoluted and disjointed—but so does Kanye.

The clothes have always mimicked his art—perhaps that’s still true.