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Kanye West is a polarizing figure. There’s no doubt the rapper has talent, but his mammoth ego, childish tantrums and profound lack of self-awareness have played significant roles in swaying people’s opinion of him. Whether you think he’s an artistic genius or an attention-ravaged tyrant, most can agree that, despite his antics in the media, the guy has consistently proven to triumph in the style department.

Since he first entered the limelight, the outspoken Chicago emcee has made some of the boldest and most influential sartorial choices ever to grace the hip-hop world. Ever the style icon, Kanye’s recent endeavors in fashion have not only been controversial, they’ve literally been an undying and ubiquitous topic of conversation everywhere; with everyone from sneakerheads to high fashion’s uppermost pantheon weighing in on all things YEEZY related.

So while we’re excited to see the artist return to his music roots with the release of his impending album WAVES, not to mention the presentation of YEEZY Season 3, we’ve decided to embark on a journey through ‘Ye’s sartorial time machine to select 20 of his best style moments. And trust me, it was no easy undertaking.

Margiela Man

Back in 2013, Kanye teamed up with storied Belgian fashion house Maison Martin Margiela to craft a range of hauntingly stunning outfits for the rapper’s Yeezus tour. Produced in the label’s Parisian atelier, the custom-made pieces were based on garments found in Margiela’s archives, including an embroidered, elongated bomber jacket, a blanket coat, printed trousers, a series of the brand’s trademark crystal-encrusted face masks and an exclusive pair of high-top sneakers.

“We didn’t pay attention to what is being said about him in the press, we just focused on what could be done with him,” a representative from MMM told Vogue. “We have wanted to work with Kanye West for a very long time, ever since he became a close friend of the Maison; supporting us a lot and coming to our shows. We like his music and the vision he had for the tour.”

PETA Enemy #1

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Sorry PETA, but we’re going to have to back Kanye’s cause this time around. Wearing what quite possibly could be a slaughtered petting zoo, ‘Ye strolled up to his homie Riccardo Tisci’s Fall/Winter 2014 Givenchy show in a getup that would surely give Cruella De Vil a run for her money.

Who Let The Dogs Out

After releasing their collaborated LP Watch The Throne back in 2011, Kanye and Jay Z were christened as purveyors of a new, so-called “luxury rap” era, which blurred the line between hip-hop and high fashion like never before. Long an admirer of Givenchy’s lauded creative mastermind Riccardo Tisci – the duo called upon the designer to conjure up the album’s cover art – there was a time where it seemed that Yeezy couldn’t be seen sporting something that wasn’t by the French fashion label.

Rest assured, there are countless looks to choose from the rapper’s “Yeevonchy” phase, but our favorite goes to this murdered-out number featuring an audacious rottweiler graphic tee.

Polo Player

Getty Images / Scott Gries

Is that Kanye…smiling? It appears so. For a minute I thought I was hallucinating. Perhaps you can recall a time when Kanye, a fresh-faced emcee from Chicago, first emerged onto the scene back in 2004. He was young, talented, had a moderately-sized ego and was really, really into Polo Ralph Lauren, like we see here when he appeared on the now defunct MTV show TRL. Though we’d be a bit overzealous if we completely credited Kanye for Polo’s comeback, he certainly played a pivotal role in bringing the iconic American label back into the minds of the youth.

Gender Bender

Getty Images / Kevin Winter

One of Kanye’s most celebrated sartorial traits is his ability to take risks, like he did here when he performed at Coachella in 2011 wearing a hyper low-cut, fairly androgynous diaphanous blouse from French label Céline’s SS11 collection. Styled with a pair of Balmain jeans, the emcee ignited a media frenzy with editors and commenters both praising and criticizing this bold fashion choice.

‘Tron’ Don

After releasing Graduation in 2007, Kanye’s “Glow in the Dark” tour was coming into fruition. During this time, the rapper’s go-to accessory were these now-iconic shutter shades, which he first popularized after wearing them in the music video for “Stronger.”

Yeezy later brought the video to life when he performed at the 50th Grammy Awards in 2008 in a Tron-esque getup complete with a light-up, LED jacket and sunglasses. Sure, wearing Venetian blinds as sunglasses looked cool on Kanye at the time, but now, the only time you can spot them are on fist-pumping juice heads who frequent EDM festivals.

Rick’s Disciple

Even just a casual stroll along the Parisian streets offers a goldmine opportunity for paparazzi. Looking thrilled as always, Kanye, who’s been a bellwether in making Rick Owens a recurring fixation among the hip-hop community and streetwear aficionados, was frequently spotted wearing this long parka coat from the designer’s DRKSHDW FW13 collection back in 2013, as well as those visvim FBT fringe kicks. If I had $2,035 to blow on a coat, I’d probably flaunt it as much as possible, too.

High Street, On Fleek

Getty Images / Jamie McCarthy

H&M/designer collaborations are already subject to hype, but throw an endorsement from Kanye in the mix, and prepare to see resale prices soar off your computer screen on eBay. When he took the stage at the Victoria’s Secret Fashion Show back in 2011, ‘Ye was seen rocking this gaudy, tropical leopard print-sleeved bomber from Versace’s H&M-collaborated line, a pair of Nike Air Yeezy 2s and leather trousers.

Black Skinhead

Kanye stirred up a significant amount of controversy when he decided to slap the Confederate flag on a number of pieces from his “Yeezus” tour merchandise. But he made a pretty solid argument when responding to the umbrage brought forth by the graphic.”You know the confederate flag represented slavery in a way…that’s my abstract take on what I know about it,” said Yeezy. “So I made the song ‘New Slaves.’ So I took the Confederate flag and made it my flag. It’s my flag now. Now what are you going to do?”

But all moral qualms aside, the merch actually looked pretty banging, and this 2013 shot of Kanye strutting out of Barneys New York in Beverly Hills serves as evidence.

Professor Kanye

Scott Schuman of The Sartorialist snapped Kanye on the streets of Paris in 2008 wearing an ensemble that adhered to all rules of color coordination. The artist kept it sophisticated with a grey suit jacket and white trousers, but added just the right amount of street flair with a star-emblazoned BAPE polo, red pocket handkerchief, striped Gucci D-ring belt and white G-shock watch.

On any other person, this getup would look like a Harvard professor going through a mid-life streetwear crisis, but it’s Kanye, so naturally it made the rounds on a plethora of style blogs’ “best dressed” lists.

#CoupleGoals

Getty Images / Pascal Le Segretain

Say what you want about Kanye’s fling with Amber Rose, but personally, I’ve never seen a rapper/model couple game look so strong (sorry Kim). I mean, what couple could possibly out-fashion one of the industry’s most prolific figures? These two can, evidently, when they rolled up at Paris Fashion Week Fall/Winter 2010 looking part ratchet, part chic, all parts #win.

‘Fresh Prince’ x ‘Pretty in Pink’

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Another one from the archives, this photo, which dates back to the 2004 MTV Europe Music Awards, displays Kanye’s preppy phase at its finest. Taking style cues from both the Fresh Prince of Bel-Air‘s nerdy cousin Carlton and John Hughes’ ’80s classic Pretty in Pink, the rapper looked especially whimsical in this Pepto Bismol-colored argyle sweater getup, ornamented with his then-signature Jesus bling necklace.

“Runaway” Short Film

For his epic short film “Runaway,” cut from 2010’s self-proclaimed “masterpiece” LP My Beautiful Dark Twisted Fantasy, Kanye enlisted New York designer Phillip Lim to whip up a range of custom-made outfits, which included this slick suit ensemble.

Dad Swag

Yet again stealing the spotlight at fashion week, Yeezy was spotted looking particularly steezy in a more subdued, “clean” ensemble while en route to Louis Vuitton’s SS16 show. Staying very on trend with a pair of ripped, stone-washed denim, tan suede Chelsea boots and an oversized off-white funnel neck sweater, the rapper proved that, even at his most low-key moments, he still kills it in the style department.

Martin “Louis” King, Jr.

Not quite the biggest fan of Kanye’s Martin Luther King, Jr.-meets-Michael Jackson phase, which came to prominence late 2008-2009, but if I had to choose one outfit from that era, it would have to be this Louis Vuitton number that he wore during Paris Fashion Week back in 2009. The gloves are a bit much, and yes, it is very GQ-friendly, but overall, we approve.

Watch The Throne

Getty Images / Jonathan Leibson

Yes, that is a leather skirt styled over leather pants. While street goth has since been given a proper burial (RIP), Kanye rocked the trend unlike any other emcee in the game back in the day, especially when he was seen wearing these bespoke garms crafted by none other than Givenchy’s Riccardo Tisci for the rapper’s “Watch The Throne” tour with Jay Z, which kickstarted in 2011.

Streets to Dries

Getty Images / Pascal Le Segretain

Accompanied by one of his favorite accessories (the leather pants, not Kim), Kanye, while heading to Balmain’s SS15 show, took on the French capital in this striking Dries Van Noten gold embroidered navy coat from the label’s SS14 collection styled with a pair of sienna brown Bottega Veneta boots.

Mr. Salmon-man

Getty Images / Frank Micelotta

Yet again, the artist pulled off a look that we’re pretty sure no one else could when he attended the Artist Empowerment Coalition Pre-Grammy Brunch back in 2005. This velvety, salmon-colored smoking jacket recalls something you’d find in the form of a sofa in a highly-outdated nursing home, but somehow, and don’t ask us how he does it, it looks surprisingly fresh when worn by Kanye, especially when styled with a matching turtleneck, suede Gucci loafers and a pair of brown-tinted aviators.

STEEZY Season 1

Alas, this article would be lacking if it didn’t include at least one shout out to ‘Ye’s very own YEEZY label. When the rapper-turned-designer unveiled the first season of his adidas-collaborated line during New York Fashion Week FW15, he graced the audience with his presence wearing a very pared-back ensemble from the collection that, while simple, embodied the range’s muted, casual-chic appeal.

For more celebrity style content, be sure to follow our Weekly Juice series and also check out Rihanna’s Best Style Moments and The Evolution of Justin Bieber’s Style.

The views and opinions expressed in this piece are those of the author, and do not necessarily reflect the position of Highsnobiety as a whole.

Words by Nico Amarca
Fashion Editor, North America