The rapper wore a pink argyle sweater and gold jewelry at the 2004 European Music Awards.
In 2004, Kanye West attended the Billboard Music Awards wearing a patterned sweater, red bomber jacket, and aviator sunglasses.
Kanye West continued his love of prep in 2004, wearing a light brown suit over a pink sweater.
In 2006, West looked cool and casual at the 2006 MTV European Music Awards in a grey zip up and grey sneakers.
In 2007, West channeled nerd chic on the red carpet, wearing a bomber jacket and crew neck sweater to the In Touch 5th Anniversary Party.
At the Los Angeles premiere of "Smokin' Aces" in 2007, the rapper once again hit the red carpet wearing sunglasses.
Kanye West has never been afraid to experiment with his style. At the 2008 American Music Award, the rapper went retro in a bright bomber jacket, printed hat, and jeans.
In 2008, Kanye West attended the 'Pineapple Express' premiere in Los Angeles sporting a bright blue jacket and his go-tos: sneakers and shades.
At the amfAR's Inaugural Milan Fashion Week event in 2009, West wore a sleek, all black ensemble, which coordinated with his then girlfriend Amber Rose.
At the 14th Annual ACE Awards in 2010, West traded in his sneakers for a classic tux.
In 2011, Kanye West posed with Carine Roitfeld at amfAR's Cinema Against AIDS Gala during the 64th Annual Cannes Film Festival in a sharp tuxedo.
Kanye West looked classic in camel-colored coach at the Maison Martin Margiela with H&M global launch event in New York City in 2012.
At the 2013 Met Gala, Kanye West looked classic, while Kim Kardashian, then pregnant with North West, wore a loud, Givenchy look.
In 2014, Kim Kardashian and Kanye West both took a more elegant route, wearing coordinating Lanvin.
Kanye mastered casual formalwear at the LACMA Art + Film Gala, wearing a white shirt, jacket, and leather pants.
In 2015, Kanye West ditched the tuxedo for a casual grey sweatsuit and his own Yeezy sneakers at the MTV Video Music Awards.
Kanye West dressed down for a casual outing with his very fashionable daugther North West in 2015.
In 2016, Kanye West wore an all-white ensemble to the 2016 MTV Video Music Awards in New York City.
At the 2016 Met Gala, Kim and Kanye took the futuristic theme seriously in custom, coordinating Balmain ensembles.
In 2016, Kanye and Kim attended the Balmain afterparty at Paris Fashion Week. For the occasion, West wore a patchwork jacket and Kardashian donned a shimmering Balmain dress.