18. Wiz Khalifa
Styled by adept creative influencer Ian Connor for a period of 2015, Wiz Khalifa nurtured a rock star aesthetic while living a similarly rock star life. Venturing on the worldwide Boys of Zummer tour with alternative icons Fall Out Boy, Wiz could usually be seen and smelled backstage or on the tour bus donning a Supreme piece or multiple. The lanky and tall grammy nominated rapper normally paired the classy streetwear with some ripped designer denim and his favorited Chuck Taylors. Wiz championed the tucked in shirt vibe for a while and his influence on the masses was tangibly realized. The edgy artist is known to throw on a high end mix of items coming from brands like Dries van Noten, Saint Laurent and Acne pairing the products with streetwear grounded accessories and garments such as the Supreme S logo six panel cap, Babylon hat and Bianca Chandon lover tee.