Kanye West's 100 Best Outfits

Image via Complex Original

WHEN: 2004

Kanye brought the heat for his first Complex cover. Nobody else in hip-hop was doing full-on prep swag like him and he actually made it look good.

WHEN: 2007

You might have been one of those people to hate on those infamous "shutter" shades that Kanye rocked in his video for "Stronger" or you could have been one of those people that attempted to wear them on the street(you fool). Either way there is no denying the effect they had on street-style, and also, style you could buy on the street, there was not one street vendor in any city in the US that didn't have them in every color imaginable, the streets are always watching. 

WHEN: 2008

Everyone goes through phases, and as they do, so does their style. Moving away from all the logos and bright colors was a natural progression for Kanye, wearing mostly muted colors, and a trucker hat to break up the monotony. Here he's rocking one of our favorite colorways of the first Yeezys, which you can still get on eBay if you've got the bank. 

WHEN: 2012

For all of you who thought the bowtie was dead, Kanye laughs in your face. For his boy Kobe's Nike commercial, he masterfully pulls off a velvet bowtie and jacket combination by French fashion brand Lanvin, and pairs them with Kobe's kicks, you might not be able to get away with wearing the same thing, but that's what makes his execution so special, learn from the master. 

WHEN: 2012

What would you wear to a fashion show, if you need help, follow Kanye's lead. During London Fashion Week, Ye rocked his favorite brand, Balmain's denim jacket and light-wash moto jeans, and to kick it up a notch, he threw on a bright-pastel knit sweater by Acne. This is a perfect example of how and why you don't need to match to look great, you just need to have the right amount of money to buy the same cool things. 

WHEN: 2012

Kanye is no stranger to taking risks with his music, and the same goes for his style. You have to be really secure to rock a leopard bomber jacket, but he does it with ease. For a recent appearance with his G.O.O.D Music signee 2 Chainz, Ye rocked a coveted leopard jacket from Givenchy's FW'11 collection. They didn't produce many, so you know Kanye had to be one of the few special people to own it. 

WHEN: 2007

Its great to see someone's style evolution from their early start to see just how far they have come. Check out Kanye's on one of his first magazine covers, his early sartorial choices included a Fila Sport windbreaker and over sized Marc Jacobs sunglasses, its a far cry from his current ballin in Balmain. 

WHEN: 2011

When you go to the airport, this is how you should look...and if you don't, you should fix that. Here Ye rocks a vintage Polo Ralph Lauren Varsity Jacket, Dior Homme waxed coated jeans, Balmain studded belt, and Jordans, keeping it mostly all luxe, but it still is relatable, and above all he turned every head at LAX. 

WHEN: 2011

When you are somewhere where the weather is amazing every day like in Cannes, France, you too would likely wear all white like Kanye. He keeps it all the way tonal with a white tuxedo blazer, white tee, and pants, and pairs it with a simple pair of sneakers from Creative Recreations Italian Collection. 

WHEN: 2011

You know you are a boss when you can call on a designer to custom-make all of your clothing for your short film, and Kanye did just that by enlisting New York designer, Phillip Lim, to create all of his personal looks. So, don't expect to be able to find these pieces...anywhere. 

WHEN: 2011

Operation Occupy Wall Street, while looking better than everyone else was a huge success for Kanye. When he showed up to the Financial District in New York City to support the movement in his plaid Givenchy button-down shirt, he also simultaneously caused the shirt to sell out in stores, and all of the online shops that carried it. This guys got influence both politically and in the fashion game. 

WHEN: 2012

Yeezy has a way of making normal gear look super dope. Here, a vintage Guns n' Roses tee gets help from a slim varsity jacket, layered chains, and Yeezy IIs.

WHEN: 2008

Kanye's visit to Conan was part of the 808s & Heartbreak publicity circuit, but he deviated from the all-gray suit and paired the tweed jacket with a bright green shirt, striped socks, and a pair of his Louis Vuitton Dons. The Lego heart stayed, of course.

WHEN: 2012

Kanye has really kicked it up a notch in his most recent sartorial endeavors. In this picture, he's rocking a blue bomber jacket, black Balenciaga pants, and yellow Balenciaga sneakers. And even though nothing is the same color, he looks great. Plus, the best accessory is the chick to his left.

WHEN: 2011

Kanye's denim shirt had a Western vibe, which surprisingly went well with black denim and Yeezys. A clean outfit that we def needed to put on this list. You know a man can dress well if his style looks awesome whether he's wearing just three items or layering with 15. 

WHEN: 2011

In the earlier leg of the Watch The Throne Tour, Kanye was seen rockign this custom Givenchy-esque t-shirt, which quickly became a coveted item on the internet. Shortly after Givenchy's designer Riccardo Tischi created tour looks for both Kanye and Jay-Z, making fashion and music history. 

WHEN: 2011

Kanye goes through style phases and in late 2011, his uniform consisted of coated denim, a plaid shirt (sometimes tied around the waist—shouts to Kurt Cobain), a plain tee, accessorized with simple gold chains and a pair of Jordans. He brought it back to basics yet he still looked like the coolest guy in the room.

WHEN: 2007

This shot was probably the first indiciation that "shutter shades" would become a thing... and we all know the man responsible.

WHEN: 2011

The Balmain red leather jacket is the statement piece that has our eBay alert on, still, and the Balmain hoodie, Cartier shades, and leather pants are all great pieces on their own. But it's amazing how all these expensive pieces thrown together can look so laid-back. It's probably the occult and heavy metal-inspired brand, Actual Pain's hat that gives it that casual edge. His outfit's so good that we barely even noticed Keri Hilson and Vanessa Hudgens next to him.

WHEN: 2010

Denim on denim, Comme des Garcons, Ato kicks, and Amber Rose...all rappers these days have appropriated at least one of those things. Ha!

WHEN: 2010

The Louboutin Rollerboy Spike slippers, leather pants, and velvet sportcoat still couldn't take our eyes off the fact that Amber Rose was pretty much naked underneath that coat. It was still cool though.

WHEN: 2008

The first Air Yeezy wasn't released until April of 2009, so it caused a riot every time Kanye wore his first Nike design before that date. Here, Kanye rocks a fresh outfit to match the Zen Gray/Charcoal colorway of his shoe, while designing his other other shoe for Louis Vuitton. 

WHEN: 2009

Kanye still wears this Levi's Trucker Jacket to this day, proof that some pieces of clothing are still as timeless as ever, even if you switch up your style.

WHEN: 2010

During Kanye's "Rosewood Movement," he pared down his flashiness and opted for a Don Draper austerity in his style. This visit to the Twitter headquarters almost makes him look like a CEO rather than a rapper.

WHEN: 2010

Part "Miami Vice" part "Opening Ceremony designing Kenzo" this neon look managed to not come off as overdone thanks to the khaki pants.

WHEN: 2010

Kanye takes the washed jeans and sportcoat look and switches it up with a cadet jacket for a welcome take on a look he would grow to detest on his twitter.

WHEN: 2010

The red suit, the Horus chain, and a leopard print shirt define a certain time in Kanye's style — when he finally learned that anything he did would be deemed fashionable.

WHEN: 2010

The good thing about this look is that it's something Kanye would wear anyway, but the fact that it just happens to be head-to-toe Bathing Ape shows how he really just has certain items he likes, and strives to get the best versions of them possible. That's true style right there.

WHEN: 2009

Still killing it in the varsity jackets, this is probably one of the more accessible looks Kanye rocked that looks good on pretty much any guy.

WHEN: 2009

This screencap from Keri Hilson's "Knock You Down" video gave us a peek at the Black/Pink Air Yeezys, combine that with his mullet, and that already earns this a spot.

WHEN: 2011

This Kanye outfit was a game changer. First of all, he's wearing his custom Balmain leather jacket (the one that says YEEZI on the back) with the patch on the front (similar to the custom Balmain patches he stuck on his white tees in the "Otis" video) which is already awesome on its own. AND at the same time, he's putting everyone onto Alexander Wang T-shirts, which pairs well with perfectly destroyed denim (which we didn't even think was possible, but obviously it is), PLUS he's still keeping it real with classic Air Jordan 1s. 

WHEN: 2009

This L.A. get-up shows how Kanye was starting to balance the casual style of his past with a more fashion-forward look, like a military shirt with epaulets. Plus, note the New Balance sneakers. 'Ye is always on something that other rappers are not.

WHEN: 2009

Kanye's iconic mullet was often accented with clean suits and bright woven shirts. This VH1 performance is a great example.

WHEN: 2009

This outfit happens to be from the same day Kanye shot the infamous "Martin Louis The King, Jr." video during Paris Fashion Week. That particular style era (which resulted in a lot of priceless quotables) was one of our favorites of his—super aspirational with a "don't give a fuck" attitude.

WHEN: 2008

Kanye made bubble vests look cool and this denim one in particular looked dope against a printed crewneck.

WHEN: 2009

Even when he was already known as a fashion plate, Kanye still knew how to keep it street. Case in point? These wheat Timberland boots.

WHEN: 2007

We can't remember the last time we saw 'Ye in a tee or varsity that baggy. But he still does rock similar stuff, albeit nowadays the T-shirts are Balmain and the varsity jackets are Versace for H&M.

WHEN: 2009

Yeezy and Amber Rose often stepped out in style, and these coordinating pastel pieces are no exception. He was still on his prep steez in 2009, just a little more refined than before with a collegiate cardigan and his favorite pair of New Balances.

WHEN: 2009

Way to match your accessories Kanye. Whether it's the red scarf and red kicks, or the fact that he brought it full circle with the Takashi Murakami Louis Vuitton bag, here's where the luxury rapper was starting to find his swagger.

WHEN: 2009

The Air Yeezys got plenty of shine on the feet of their designer, and he paired them with anything and everything — including a denim vest.

WHEN: 2010

When Kanye goes black tie, he is probably wearing velvet slippers and a well-cut tuxedo, because he knows what he's doing.

WHEN: 2003

When 'Ye donned this Astro's throwback jersey it was at the height of vintage jersey pandemonium, every rapper was trying to get their hands on one, but 'Ye crushed it by rocking this one, it's extremely rare, making it even more of a style statement. 

WHEN: 2009

During this show at London Fashion Week Kanye showed he could be as dandy as any other British gent. While the pants, shirt, and blazer are conservative, it's his colorful accessories that make this outfit pop.

WHEN: 2009

Points to Kanye for being on bowties before they were over, extra points for the pink G-Shock, and bonus points for the grayed-out varsity jacket.

WHEN: 2008

Kanye killing it in nerd glasses, green pants, and a Y-3 hoodie.

WHEN: 2004

Before you could spot him head-to-toe in Lanvin and Balmain, Yeezy was actually a model for LRG. Don't worry, he still looked fresh then, too.

WHEN: 2008

Kanye shows some support for Pharrell by rocking Billionaire Boys Club, and keeping it fresh with some Aqua 8 Jordans at LAX. That's flying in style.

WHEN: 2008

Was Yeezy the one to bring denim jackets back? He kept it casual in the American classic during the Louis V fashion show in Paris, but that scarf out the pocket really swagged the outfit out.

WHEN: 2008

We learned how to layer from 'Ye. He wore Keffiyeh scarves in the Graduation-era just like the rest of us, and just like the rest of us he let it go pretty fast. Before we got PC though, the mismatching patterns of the scarf and patchwork shirt looked awesome.

WHEN: 2008

If heartbreak gives us the ability to dress like this, then sign us up. The 808s signature gray tweed combined with the chambray oxford was already fresh, but adding the Black Cement IIIs in there? He straight killed it.

WHEN: 2008

Kanye's uniform of a varsity jacket + distressed denim + sick sneakers was an untouchable combo. An outfit like this seems so simple now, but he outshined his stylish dinner companions (Jay-Z and Aziz) easily that night.

WHEN: 2009

Surprisingly, the dope varsity jacket that Kanye was seen wearing in early 2009 is an actual letterman jacket from Kamiakin high school. If only Kanye put our high school on the map, we would have ranked this outfit higher. 

WHEN: 2008

One of our favorite Pastelle designs, this tiger jacket had all of Kanye's fans fiending for one just like it. The jacket alone would have made any outfit awesome, but the 7s he threw in there makes it even better.

WHEN: 2009

This iconic photo by Tommy Ton became the basis for the "Fishsticks" episode of South Park. Gay fish jokes aside, this was the marked beginning of Kanye's foray into the world of high fashion.

WHEN: 2008

This was one of the few times Kanye rocked a beard, but nevermind the facial hair, dude is wearing Visvim shoes! The Japanese brand with a cult-following didn't really pop-off with cool guys before 2010 so this blue outfit is one for the books...the books of Kanye's trendsetting moments.

WHEN: 2010

Kanye West is no stranger to the black tie look, but the air tie is killing it... only to be overshadowed by the boobs on his slippers. Swerve!

WHEN: 2008

Kanye made Moncler bubble jackets and vests hot in The States. No Americans were on this before he was, and it's surely because Europeans weren't rocking this shit with Jordans. 

WHEN: 2008

This photo from the Graduation era shows how Kanye really started a movement with his signature style: streetwear, plus at least one designer piece. The BBC hat and Bape flannel kill even harder with the addition of Gucci moccasins. 

WHEN: 2008

The original combiner of streetwear and high-end, Kanye continued to look cooler than everyone else by wearing a BBC/Ice Cream sweater with his Yeezys and a luxe Louis Vuitton Damier backpack.

WHEN: 2006

It seems Kanye had an affinity for red long before his iconic appearance at the VMAs. Here, he coordinates colors with Pharrell, who's also since stepped up his style dramatically.

WHEN: 2008

This outfit was killer. Of course, you can't be at a N.E.R.D. show without Billionaire Boys Club on, and Kanye repped Pharrell's brand aptly with his BBC hat. He was still on Ato Matsumoto shoes in '08 and pulled the whole look together with a crazy Bape camo cape. Definitely a refined streetwear look that only Yeezy can pull off.

WHEN: 2008

Kanye wore what we considered the weirdest shit and made it look cool. And all of a sudden, looking like a modern-day urban gladiator was awesome. 

WHEN: 2010

Hardly any other rapper could make leather pants look this dope. Couple it with the black/cement 3s, jean jacket, and Tupac-style bandanna, and you've got a kit that's fire.

WHEN: 2008

Kanye performed his Daft Punk-sampled hit, "Stronger" at the 50th Grammy Awards and wore the light-up jacket from the track's music video. He even paired it up with the shutter shades he made so popular in 2008. This is definitely one of his most memorable looks to date.

WHEN: 2008

This is an outfit that defines the hypebeast of the late aughts. When guys wear varsity jackets, chinos, and Jordans now, it's just because they've finally caught up with Kanye from back in '08. He made Aqua 8s and G-Shock watches look better than anyone.

WHEN: 2007

Rappers who take risks with clothes tend to be fans of Jeremy Scott. Kanye then, and A$AP Rocky now. Kanye showed up at NYFW with the designer wearing classics like a striped sweater, washed jeans, and Jordan 3s, but upped the ante with the fat Gucci link chain.

WHEN: 2011

There's two times to pull out your stunting gear, one of them is for fashion week, the other is for fashion weekend aka All-Star Weekend. Ye pulled out all the stops in all Balmain, and J's on his feet. Here is when he debuted the Balmain "Teddy" varsity jacket which is one of the most expensive pieces from the mens line, being priced at over $4,000. 

WHEN: 2007

When Kanye was initially messing with super designer clothing, he opted for pieces with more visual cues as to what he was rocking — in this case, YSL and Gucci. Since then, he's gone to wearing pieces straight from the runway that haven't even hit stores yet.

WHEN: 2007

Kanye is killing it in those Supreme quilted blazers! No wonder his Louis Vuitton shoes came in a red colorway.

WHEN: 2007

Still on his shutter shades tip, Kanye was unfraid to start mixing his love for suits with his love for Jordans.

WHEN: 2007

Yoooo... Visvim kicks and a baller scarf? This is starting to look like the Kanye we know and love.

WHEN: 2011

The big news of the night might have been Jay-Z and Beyoncé's baby, but people were still talking about Kanye's ombré chambray ensemble. Denim on denim is usually seen as a fashion don't, but Kanye made it ok.

WHEN: 2011

A style star is born, leave it to Paris fashion week to make you want to pull the big guns out your closet. Dressing the part and staying true to his aesthetic Kanye rocks a bright red tuxedo jacket, simple T-shirt, his favorite Balmain utility pants, Givenchy shirt wrapped around his waist, and finishes it off with some Jordan's, swagger on a hundred-thousand-trillion. 

WHEN: 2007

The dark colors of this outfit mean that the leopard-printed kicks get more shine, which we're sure is how Kanye wanted it.

WHEN: 2009

When Kanye debuted his bright red Louis Vuitton sneakers, of course he had to give them as much shine as possible. How did he achieve that? Simple, by rocking them with dark suits.

WHEN: 2009

This stunning image that Scott Schuman aka The Sartorialist took in 2009 captures Kanye giving stone face in an all-black outfit that screams luxury. The only color comes from the reflective sunglasses. Badass. 

WHEN: 2008

Kanye was the musical guest on David Letterman's show in November to promote 808s & Heartbreak and he stunted in a Pastelle varsity jacket and Aqua 8s when he arrived on set. As always, he was on the raw denim trend before the masses got with it, and the camo Louis Vuitton duffel just upped the whole outfit to another level.

WHEN: 2011

When Kanye and Jay-Z hit the stage at the Victoria's Secret Fashion Show, he stunted in this Versace for H&M varsity jacket before the shit even came out. That's how big he was.

WHEN: 2010

The Rosewood Movement hit the streets strong in the summer of 2010. Kanye and his crew wore Dior Homme suits and made everyone else feel horrible about themselves for looking so bummy in comparison.

WHEN: 2008

In the summer of 2008, Scott Schuman of The Sartorialist caught Kanye wearing a perfect outfit. The gray suit jacket, white pants, and striped D-ring belt are absolutely classic, but 'Ye added his usual flair with a bright red pocket square, star-printed polo, and of course, a white G-shock. 

WHEN: 2008

Yeezy was up on brands like Jeremy Scott for adidas originals and Comme des Garcons PLAY way before anyone else in the rap game. This 2008 photo shows it.

WHEN: 2007

One word: G-Shock. This was the birth of a massive trend in streetwear.

WHEN: 2008

This red Moncler was FIRE when Kanye started wearing it. Bubble jackets never looked this good since Nas' Triple Fat Goose days.

WHEN: 2008

From a shoot that never made it to print (exclusive!!!) All MCM everything. This outfit was the result of Kanye and Taz Arnold spending more time with each other to make fashion show rounds. This was also the era of that birthed the infamous "Fish Sticks" joke, but hey, that's what makes the outfit even more memorable.

WHEN: 2004

Kanye loved to mix up pastels and bright colors in his early days. Now, it might not be considered the pinnacle of style, but this student of fashion was learning about color blocking fast.

WHEN: 2011

Yeezy made the white tux jacket over a T-shirt and worn jeans look dope, but it was the first appearance of the Don C. snapbacks that had everyone going wild. It was the perfect accessory to cap off the "luxury meets streetwear" look that he had perfected.

WHEN: 2007

Nobody heard of Ato Matsumoto sneakers until Kanye started wearing the high-tops everywhere in 2007. Then of course, other celebrities followed suit.

WHEN: 2011

In January of last year, Kanye eliminated all his other fur coat looks off this list by wearing this here outfit. He paired the grandiosest of grandiose fur jackets with leather pants, Retro 3s, a swaggy snakeskin backpack, and a "Fuck PETA" attitude that we can only salute. Damn.

WHEN: 2006

In his early days, Kanye was super into streetwear. He even took these influences into his line Pastelle. As such, he often rocked trends like full-zip hoodies. But hey, at least his were BAPE, and he rocked them in a lookbook, no less.

WHEN: 2011

Who could forget the impact this single outfit had on fashion? His public co-sign of designer Phoebe Philo propelled this Cèline tunic and the label into the world of hip-hop. The Burkman Bros. bracelets he stacked up on his arms helped usher in a whole trend of guys layering colorful bracelets. Love it or hate it, you can't deny the impact of this summertime look.

WHEN: 2005

This outfit was huge. The tearaway Geoff McFetridge Nike Vandals had a sick design underneath the first canvas layer of the shoe which could be custom destroyed by anyone who had a pair. And not anyone had a pair.

WHEN: 2003

An O.G. streetwear look featuring a Supreme hoodie, baseball cap, gold watch, and pre-Jesus piece chain.

WHEN: 2008

This gray suit was a clean look that preceded the "Rosewood Movement," but perfectly exemplified the stark, emotional climate of 808's & Heartbreak. It was simple, clean, yet the prominent Lego heart pin was all the panache necessary.

WHEN: 2003

The College Dropout look was characterized by plenty of rugby stripe shirts. The kind that would make Yeezy say "Ralph Lauren was boring before I wore him."

WHEN: 2006

An oldie but a goodie, Kanye West's co-sign of the LRG "Dead Serious" hoodie continues to affect the aftermarket price.

WHEN: 2011

Kanye West let the dogs out. Of course he put rappers like Pusha T, Jay-Z, Swizz Beatz, and Kid Cudi on Givenchy. He co-signed the brand so hard he enlisted Creative Director Riccardo Tisci to art direct plenty of Watch The Throne, ranging from custom shirts, the album cover, and set design.

WHEN: 2008

When you think of the now-defunct Pastelle, this outfit should be the first image that comes to mind. The flashy jacket with the even flashier patchwork on the back has been on every Kanye fan's wishlist since its first appearance. Which is why the news that Kanye deaded Pastelle was even harder to take.

WHEN: 2011

When images of the customized YEEZI jacket first popped up, we weren't sure what to make of it. In retrospect, we now do know what to make of it: it's awesome. Now everyone is making their one custom leather jackets

WHEN: 2003

In this Complex shoot, Kanye was rocking a custom Dr. Romanelli Nike jacket and sick sneakers. Nobody had what he had. He's always been down to rock unconventional designers from the start.

WHEN: 2010

A year after Kanye's controversial moment with Taylor Swift, he graced the stage and redeemed himself with a stirring performance that showed guilty self-awareness and musical genius at the same time. This custom Phillip Lim suit would make multiple appearances during many My Beautiful Dark Twisted Fantasy performances, including his seminal appearance on SNL, where for the first time, the show's musical backdrop was rendered in stark white instead of the usual black.

Kanye had said that his aim was to be the next Michael Jackson. The red-on-red outfit was a definite homage to the King of Pop, and further cemented West as a true hip-hop icon.