Era of Prominence: 2005-2006

Post-Late Registration, Kanye's career was shining so hard he had to shield himself from it, which may be why he opted to rock a variety of sunglasses—even when it was dark or indoors. His red carpet attire leaned toward the obnoxious than the austure—wide peaked lapels, square toed white shoes, and white dinner jackets with coordinating white-rimmed aviator shades. His performance attire was definitely more streetwear friendly, and he made an impression showing up to the Brit Awards in a Hedi Slimane-designed red cadet jacket from Dior Homme's spring 2006 collection.