Era of Prominence: Late 2008-Early 2009

Foreshadowing his later, bolder adoption of the color red, Kanye began incorporating the color into his wardrobe, usually worn with darker shades like black—save for a performance at the Z100 Jingle Ball. Perhaps the Chicagoan meant to rep the Bulls, but with custom Phillip Lim jackets and Louis Vuitton sportcoats done up in the bright color, this stage was a clear signifier that Kanye wanted to take the gap between the hip-hop and fashion worlds to a different level.