Breaking Down Kanye West's Most Iconic Looks

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Breaking Down Kanye West's Most Iconic Looks
Paris Fashion Week



3/31/2021 2:15 PM

I will always love Kanye West...but I get it, and believe me being a super fan for the past 20 years has not been the easiest hat to wear in social circles (especially ones where art is a nonissue). For the last two, man’s been having a rough go: he’s on the bad end of his divorce with the most powerful non-politician in America (fight me), his music has lost its relevance for the first time ever, and the buzz words “Failed Presidential Attempt” make it seem like Kanye assassinated his own career.

To top it off, last week it was revealed that he’s ya only worth $1.6 billion and not his self inflated $6.6 billion. But if you’re a real Kanye fan you know that all of this is besides the point. For too long people have sit around debating the merits of Kanye's art vs his outsized ego and public antics and that is exactly what he wants. But before Kanye’s foot in fashion totally capsized his musical output, there was a time when Kanye West was the most important artist in music, talented at using controversy and image to service his transformations. Anything Kanye did in fashion or in the press was just him being in total control of his art. In other words, it’s not just an album with this guy, it’s literally a whole reinvention. Looks yes, but also through media communication, live performance, interview topics, even his outbursts are on brand with his projects…he’s the David Bowie of rap. Or maybe he’s John Lennon, brash, rude, brilliant, outspoken, wildly creative (...and probably on meds all day), But while Lennon used activism as his parallel channel, Kanye used textiles to connect his art to another medium.

It’s clear to see why this man thinks everything revolves around him; it's because his entire brand rests on his back. Kanye makes the beats, coordinates the look, raps the lyrics, designs his tour sets and merch, and does a tonne of press every time he has a project out. His fashion line is gargantuan. That ladies and gentlemen is a renaissance man. So in celebration of Kanye’s name popping up in the news as it does, a few of us at SMACK got the peanut gallery together to talk about the man, the rapper, the fashion icon, Kanye West and his most famous, weirdest, and best moments in fashion. Yeezys were notably not included as these were a commodified product and not a symbol of his music.

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“The Stunner Shades”


Designer: Alain Mikli

Lyric: “I feel the pressure under more scrutiny, and what I do? Act more stupidly.”

Ian: Would you get pulled over for distracted driving with those things on?

Blake: This is the dumbest piece. Glasses without lenses were one thing, but glasses with blinding shutters? High fashion's out-of-touch tendency to blatantly cast practicality to the wind. A great way to alienate vast swaths of the population. Sure, it's a statement, but a pyrrhic victory at best.

Kate: I am my own MUSE

Aaron: Horrendous but iconic nonetheless. it really fit the sound though. He's super good at finding a look to match his persona and music.

Bianca: True, so damn prolific and pervasive, even though there was basically zero practical value. This might be like Kanye's most iconic fashion moment/trend/statement

Ian: I remember in highschool everyone who went to Glow in the Dark (and believe me it was about half the grade) showed up the following day with them and thinking to myself that maybe 15 isn’t too young to try drugs after all.

The Feel Like Pablo Line


Designer: Kanye West

Lyric: “I feel like Pablo when I’m workin’ on my shoes, I feel like Pablo when I see me on the news. I feel like Pablo when I’m workin’ on my house, tell ‘em party’s in here, we don’t need to go out.”

Blake: We are still in this era - mid-Zeitgeist Wheelie Pop - and so I cannot comment. To aptly quote the "zeitgeist" coiner, G. F. W. Hegel, "The owl of Minerva takes flight only when shadows gather."

Aaron: Reminds me of everything else about Life of Pablo: simple, low effort, likely rushed...and I love it. The Pablo Escobar to Picasso parallel is kind of whatever, kind of felt like he was scrolling google images while Narcos was on.

Kate: Kasual Kanye is fire. I’d worship this look any day.

Ian: “minimalist rich guy who is at the point in his career where he can wear whatever the fuck he wants and people will praise him for his keen eye for ‘fashion.’” and/or “a BMX rider who smokes weed and hangs out under viaducts on weekends.”

Kate: Bless Up - color and vibe on point. 

Nate: If I recall correctly, this shit was offered as merch on tour. Around Yeezus, it seemed like he got really good at commodifying his merch as they would sell out crazy fast online, people were flipping shirts, etc.

Yeezus Tour Masks


Designer: Maison Martin Margiela

Lyric: “Yeezy season approachin’ fuck whatever y’all been hearin’. Fuck whatever y’all been wearin, a monster about to come alive again.”

Aaron: Like everything Kanye does, people were initially mad that he didn’t show his face at concerts as if he’s any more expressive than the bouncers around his stage. Yeezus is far from Kanye’s best in my opinion, but as a “Kanye phase” it’s likely his most cohesive. The vision was so clear from the marketing, to the outfits, to the music, to the Zane Lowe interview to the TV performances.. All the while he came out looking like some rock star bad guy. All of this obviously culminates in the infamous Yeezus tour which depending on who you ask was either the greatest concert of all time or the greatest show that never happened.

Blake: I take back what I said about the asinine impracticality of high fashion. The Diamond Mask was dope and there is simply no two ways about it. I wish I could wear it all the time; in fact I am wearing the mask right now. How am I even typing this I can't even see?

Kate: This look screams America, Fuck Yeah! But also, I’m scared. 

Nate: Him and Bjork are some of the few people who don't look like a dumbass rocking a mask on stage, MF DOOM and the Residents too lol.

Bianca: Daft Punk and Slipknot can be placed in the good bin..deadmau5 goes in the 'looking like a dumbass' category. Also, I still pronounce it "dead maw 5" when typing out.

Aaron: I love when he did the 30 minute version of “Runaway” and that woman kept him telling to take off the mask and he had the autotune going and he was freestyling over piano: I need the mask because without the mask I can't express myself and he was like bitch I'm motherfucking kanye west!!! Anywho they threw her out.

“The Pink Polo”


Designer: Ralph Lauren

Lyric: “Ralph Lauren was borin’ before I wore him”

Crater: He's tried to immortalize this fit on multiple tracks. Is it as iconic as he's made it out to be? I think Cam'ron was rocking the pink mink first, dating back to '02.

<div class="tenor-gif-embed" data-postid="3558343" data-share-method="host" data-width="100%" data-aspect-ratio="1.775"><a href="">It Ain't No Ralph Tho GIF</a> from <a href="">Kanyewest GIFs</a></div><script type="text/javascript" async src=""></script>

Aaron: Honestly, I think so. Don't forget this was the bling era and Kanye very effectively used fashion as his part of his wide arsenal of techniques to set himself apart as a non-violent family values guy. Agreed, Cam'ron doing the coat was the direct inspo I think...but still are we sitting around here debating how Purple Haze paved the way for anything as brilliant as it was. The pink polo was kind of like Rubber Soul, not his best but perhaps the defining moment that would set the path for what was to come. It put him on the map.

Ian: Honestly, there haven’t been too many rappers who could pull off this look before the LVD put on a backpack. Most of that is probably Kanye’s swagger and that he oozes confidence in whatever he’s doing to the point where people got pissed off almost right away. Ok also, this will always be peak Kanye to me, if not just for the fact that he was about to lead into one of the most legendary stretches of any pop music career. It’s kinda like Lebron on the Heat winning a couple rings and then going to the Cavs four years later to immortalize himself; this would be Lebron in high school.

Jared: It may not be an iconic fashion statement, but it is an important iteration of Kanye West, the persona. It showed that he was going completely against the cultural grain, something that for better or worse, would continue throughout his career. Also it's a look that is constantly referenced in rap music post-College Dropout. The first lyric that comes to mind is from Drake's "Know Yourself": 

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Bianca: did the trend of layering multiple coloured polos with popped collars stem from this? RIP to those days. Also can I just point out Kanye is like never ever smiling and here he looks like a happy-go-lucky guy, almost could be a dad who brings everyone out for ice cream.

Ian: I’m just picturing this outfit on a whiteguy named Chad. Chad’s dad rakes 450k and whenever his son gets into fights at bars after drinking way too many tequila shots (likely getting pummelled, also do barfights still exist on zoom happy hours?) he rants on about his Dad’s said profession how his 401k is gonna be stacked by the time he’s 40 and a lawyer.

Aaron: That is probably exactly what he was going for.

The Rottweiler Tee


Designer: Ricardo Tisci

Lyric: “I made Jesus Walks I’m never going to hell. Couture level flow is never going on sale. Luxury rap, the Hermes of verses.”

Aaron: Watch the Throne was a sick album. Enjoyed the whole cocaine, hennessey and Jordan highlights aesthetic thing they were going for. Just 2010’s pre-trap excess at its climax. I mean isn’t that why they played the song 20 times? Loved hearing rumours about Kanye wanting to increase the budget and Jay quickly shooting him down. All of that to me is pretty much in this shirt which if you told me was Ed Hardy I’d probably believe it. Just remember while Jay-Z was buying Basquiats, Jeff Koons, Picassos, and George Condos, Kanye walked around with “dogs playing poker” by givenchy on an oversized tee.

Kate: Why? 

Bianca: I think mom bought me a knock off or something inspired by this in grade school.

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<p><a href="">WATCH THE THRONE MNI-DOC</a> from <a href="">Orange Culture</a> on <a href="">Vimeo</a>.</p>



Designer: Jacob & Co.

Lyric: “Some wear a suit and tie, they don’t wanna remain average, some wear a suit and tie like a chain in a straight jacket.

My chain heavy stopping that traffic, coppers harass us, the D.A. attack us want us in chains like B.A. Baracus.

Kate: Taking names and serving looks. Red is Kanye’s color. 

Aaron: This is about as flamboyant as Kanye gets. He was inspired by Richard Pryor. The suit, not the chain.

Nate: Had no idea, that's awesome. Him rocking that red suit at the 2010 VMAs was sick

Aaron: Yes, seeing as it was the year after he became a pariah from the Swift thing. He showed up in a red suit and played “Runaway” on a sampler on a stage of clouds. Meanwhile, she sang some song she wrote that was boring and spiteful.


Phoebe Philo

Virgil Abloh

Kim Jones

Jeremy Scott


Oliver Rousteing

Alber Elbaz



Hedi Slimane

Kris Jenner




“The Lego Brooch”


Designer: Kanye West

Lyric: “Okay, I'm back up on my grind. You do you and I'm just gon' do mine

You do you 'cause I'm just gon' be fine. Okay, I got you out my mind”

Aaron: Get it? He had his heart broken and he pieced it back together!

Kate: I came to slay and break your heart. Damn. 

Bianca: Why does this remind me of editing on Piczo? You know? Like making the whole pic black and white with one colour standing out?

Blake: For me this is the ultimate era for Kanye's wardrobe. In 2008 I used to B-Line to school daily, back and forth through the Broadway corridor staring up at the cardstock advertisements lining the roof of the bus. I remember seeing the 808's album decal showing up one day and staying there for a whole year. I didn't listen to rap at that time and had basically no knowledge of Kanye beyond his fitted, casual tweed suit splashed with the red of his heartbreak pendant (occasionally literally on his sleeve). Soon, all the guys at school started dressing-up like him: slim-fit button-up Oxford, patterned sport jacket, skinny pants cuffed right at the ankle. It was a good look; still is. It attests to the fact that in many ways Kanye's fashion precedes his music.

Ian:  The button up to the top and the shag rug looking suit is all on point. I wish I wasn’t such a Gweilo and rock these kinda outfits.



Designer: Kanye West

Lyric: “Now if I fuck this model and she just bleached her asshole.. and I get bleach on my T-shirt

I'mma feel like an asshole.”

Bianca: you know $120 for a shirt is insane but James Perse has been doing this for a while so is it really that crazy?

Ian: Bernie Madoff just woke up from one of his daily naps in prison and is placing some calls to see if Kanye needs any help in his newest venture.

Blake: Yeezys go for a lot on StockX. A number of years back I tried to short the market and found myself in a financial tete-a-tete with sneaker heads.

Ian: I mean, come on...this is highway robbery. To my knowledge, I don’t think Kanye was the first person to slap his name to a cotton t-shirt and run a 1000% profit margin +. The description of the garment is great too. “Ribbing at the Neckline?” “Reinforced Neckline and Shoulders?” These product specs sounds like I’m online shopping for a hazmat suit. This should probably be put on the shortlist of the greatest American scams. 

Blake:  This white tee gets a bad rap but if you know where I can find a whiter tee for less money please dm me.


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The Coachella Outfit


Designer: Phoebe Philo

Lyric: The Lyor Cohen or Dior Homme that's Dior Homme not Dior homie, The crib Scarface couldn't be more Tony, You love me for me could you be more phony?


Aaron: I remember seeing this. His outfit was just bananas and it was his first show post MBDTF. He came down on line an air hangar or whatever. just wow kanye. The beginning of his like high high fashion phase, which I don’t think ever ended really. The first albums were all about bapes and Ralph and GAP and now he was referencing designers that hype beasts actually had to google.


Bianca: actually I like this -- colours, geometrics...

Ian: This feels like his attempt at embracing Middle Eastern/North African culture. What’s next? Open up a Persian rug store? 

A. Wouldn’t put it past him 

B. He’d make it work 

C. How can I invest?


Yeezus Tour Confederate Tee


Designer: Kanye West

Lyric: “Doin’ clothes you woulda thought I had help but they wasn’t satisfied unless I picked the cotton myself.”

Blake: Not only was this line of merchandise shamelessly draped in the confederate flag, but also featured tattoo-like skulls in traditional Native American headdress. Kanye couldn't get away with either but that's beside the point as this was clearly another instance of provocative fashion, made even more egregious by its mass market availability. 

As if Kanye hadn't appropriated enough, he copped the sacred layout of heavy metal tees and pushed it as expensive, cutting edge street wear.  It's not my place to gatekeep the heavy metal aesthetic, but can we at least pretend that authenticity is worth striving for?

That being said, I remember how quickly this sold out before showing up on grey market sites like StockX for beaucoup bucks.

Aaron: Do you work for StockX now or something?

Ian: Kanye being Kanye. The guy pushes boundaries and definitely knew throwing on a flag emblematic of America’s racist past was bound to stir the pot. Unfortunately for Kanye the confederate flag will never be in good taste and this is a bigger swing and miss than Carlos Gomez (follow zebra).

Aaron: at least it’s not a MAGA hat.