Kanye West has more-than-successfully transitioned from a behind-the-boards producer to a controversial yet highly-sought after rapper, and his wardrobe has gone through a noticeably more couture-centric makeover as well. Now nearing his sixth studio album, "Yeezus," the Louis Vuitton Don has traded in the polo shirts and bowties for grey t-shirts and leather. Take a look at West's fashion evolution over the years and tell us in the comments section below which of his outfits were a hit and which were a miss.
Throwing up the diamond hand-sign for Roc-A-Fella records in 2003, Kanye West sports an oversized getup. Looking disheveled, it's obvious he hasn't entered the celebrity limelight.
On the video set for "College Dropout" in 2004, Kanye appears sullen in a Ralph Lauren Polo sweater. The preppy Macy's fit was an upgrade from the previous style.
Posing with his signature "Dropout Bear", West adds some flair in a rugby sweater, Polo dress shirt and bling. The backpack, most likely a Louis Vuitton manpack, became a signature accessory during the Dropout era.
Kanye awkwardly faces press at the 4th Annual BET awards in 2004. His lavender sweater tucked into ill-fitting khakis does nothing for the baby-paunch -- and is that corduroy? West's sterile, prepster look is uninspired and beyond his age.
Getting a tad flashier with the argyle, West reveals his pastels at the 2004 Billboard Music Awards. West, who in a few years redefines the relationship between visibility and sunglasses, sports an understated pair here.
West's love for ornamentation and detail comes across in the hair, but unfortunately not the suit. Wearing something a tad fitted is flattering, but the all-white leisure suit is too reminiscent of a KC& Jo-Jo video.
West transforms from Diddy in the 90's to the Saturday Night Fever prom king. Although oddly haphazard, the attention to accessories and more precise tailoring becomes apparent.
At the 2006 Grammy Award's Kanye's swagger goes a step too far. With so much leather, gold and man-chest medallions, did West forget that he's NOT a drug lord from the 1970's?
But despite the ludicrous nature of West's Grammy outfit on the carpet, he came out a winner. Minimizing the red carpet's guido valentine for a Dick Tracey pastel situation, Kanye wide-stances with his winnings.
The 2006 Grammy's thrust Kanye into the limelight as a questionable fashionisto. At the 2006 Brit awards, Kanye mixes jeans and trainers with a Sgt. Pepper's band jacket, white shades and golden girls.
At this Fendi launch party in Tokyo in 2006, Kanye brands his head with the double-F logo. Associating himself consistently with brands such as Louis Vuitton and most recently Phillip Lim becomes more important to West. Although, pulling a Lil' Kim a la Vuitton seems a little extreme even for Tokyo.
West moves from looking like a dapper pimp to a comfortable hipster in this sweater combo. The white pants are still not tailored, but fitting a tad tighter.
At the 2007 Annual Songwriters Hall of Fame and ceremony, West oddly combines a refined British gentleman with hangover brunch in this jeans and blazer mash-up.
In October of 2007, West and his ex-fiancee Alexis Phifer attend the Christian Dior show during Fashion week in Paris. West layers well in this blazer and button-down with high-top trainers. Glasses become a consistent accoutrement to West's wardrobe.
At the BET Hip-Hop awards in 2007, West is looking rather hippstery in red pants, a tailored khaki jacket and Louis Vuitton scarf. His tinted aviators add a nice touch to the outfit.
At the 50th Annual Grammy Awards in 2008, Kanye's iconic slatted glasses featured in his collaboration hit "Stronger", go viral. Available in any mall or street corner across the country, Kanye invents a fashion meme destroying visibility.
At the Thakoon presentation in the fall of 2008, West wears a gray tweed suit with tortoiseshell specs. The neatly buttoned shirt combined with a hint at suspenders and boating shoes is a flattering outfit. This new "distinguished professor" look sporadically appears again.
Once West became a bona fide fashion maven (he collaborated with Louis Vuitton on a line of sneakers around this time), he fluctuates between classy streetwear and formal attire. Kanye never produced his personal line, Pastelle, but we did get to see this throw-back jacket during the 2008 American Music Awards.
At Flaunt Magazine's 10th Anniversary party in late 2008, West goes Black Tie formal in a tux with an oversized bow-tie and a Louis Vuitton gray mink scarf.
Kanye West flew into Paris for the Louis Vuitton show during fashion week to see the debut of his sneaker collaboration with LV. Here, West stands with his "fashion idol" designer Marc Jacobs in a well matching outfit with a proud-mullet/fauxhawk 'do.
Three days after the Louis Vuitton show, West appears front-row at Lanvin wearing a dapper red jacket and brown riding-gloves with matching aviators and fauxhawk. His combination of materials and colors (see pink accent in lapel) is refined yet energetic.
At the 51st Annual Grammy Awards in 2009, West wears gloves, a sequined jacket and a fully-buttoned shirt reminiscent of a Michael Jackson outfit, during his performance.
Bringing back the nod to professor-prep, Kanye sports this letter jacket next to girlfriend model Amber Rose during the Kai Kuhne Fall 2009 after party during Mercedes-Benz Fashion Week.
Riffing off of his 2008 Thakoon suit, Kanye wears a neatly tailored outfit during London Fashion Week in Feburary, 2009. The bright accents from his mini bow-tie and camel-colored shoes are lovely with the blue/gray palette.
Model Amber Rose influenced Kanye's fashion choices, specifically in the realm of matching outfits. Here West and Rose attend the Vivienne Westwood Red Label show as part of London Fashion Week in matching denim and black getups.
And then there was the 2009 VMA debacle, where Kanye departed from his dapper appearance to portray a bad-ass motorcycle thug with a bottle of Hennessy. This leather shirt and jeans combo was a strange choice for a fashion maven (though not as strange as stealing the mic from Taylor Swift during the show).
Kanye appeared on PETA'S worst offenders list in 2009. We can understand why, after seeing this massive fur coat matching with Amber Rose at the Louis Vuitton show during Paris Fashion Week in early 2010.
In this picture of Kanye with LeBron James during his NBA announcement in July 2010, West mixes a casual T-shirt with a large-lapelled sports jacket. Looking like he supports the Miami decision a la wardrobe choice, Kanye is both primped and relaxed.
Kanye West earned his crown as the King of Bling at New York's Yankee Stadium on September 15, 2010, wearing a gold shirt, a red Givenchy suit and a necklace that would rival any of Cleopatra's.
The rapper-cum-designer rocks a casual and cool look as he bows to the applause of a few hundred fashion-industry professionals after the Dw by Kanye West show during Paris Fashion Week on October 1, 2011.
Appearing to have stepped out of a beautiful dark twisted fantasy, Kanye -- dressed in a dapper, customized tuxedo jacket and black leather pants -- strikes a pose with Mark Fast at a dinner hosted by the Canadian designer on February 7, 2012 in London.
Meow! Rocking a leopard-print Givenchy jacket, West looks purrfectly sharp with rapper 2 Chainz as they visit 106 & Park Studio in New York City on April 9, 2012.
Yeezy and his recent love interest, Kim Kardashian, wear matching black leather pants as they indulge in some ice cream while shopping at Kirna Zabete and Louis Vuitton stores in SoHo, NYC.
The self-proclaimed "Louis Vuitton Don" lives up to that debonair title by wearing a sharply tailored black suit and bowtie at the "Schiaparelli And Prada: Impossible Conversations" Costume Institute Gala at the Metropolitan Museum of Art on May 7, 2012 in New York City.
Drenched in an unfussy, chic ensemble, Kanye and Kim Kardashian (aka "Kimye"), along with Jay-Z, attend the debut of 'Ye's sort film "Cruel Summer" in Cannes, France on May 23, 2012.
Kanye West arrives at the Christian Dior Spring / Summer 2013 show as part of Paris Fashion Week on September 28, 2012 in Paris, France.
Kanye West attends the Maison Martin Margiela with H&M global launch event at 5 Beekman on October 23, 2012 in New York City.
Ye' attends a cocktail party at NYC's Versace Boutique wearing his own Air Yeezys on October 24, 2012.
Kanye West brought out his signature leather kilt out of his closet for his performance Sandy Benefit Concert in New York. 'Ye was first seen wearing the kilt during his and Jay-Z's 'Watch the Throne.'
Kanye West is one to surprise. During his three consecutive "7 Screen Experience" shows at Atlantic City's Revel Resort in December 2012, 'Ye wore eccentric head gear such as a crystal Maison Martin Margiela mask.
Kanye West roams NYC's Soho with his girlfriend, Kim Kardashian, both rocking leather, on April 23, 2013.
Kanye West keeps it dapper when attending the 2013 Costume Institute Gala - PUNK: Chaos to Couture at Metropolitan Museum of Art with his boo on his side on May 6, 2013.