Grimes - There is no denying that Canadian musician Grimes is one of the most stylish and unique music stars of today.
Diana Ross - The Supremes, and through her illustrious career as a solo artist, Diana Ross has always dressed her absolute best.
Leonard Cohen - As if his smooth and haunting baritone voice wasn't enough, Canadian singer-songwriter Leonard Cohen was usually the most stylish man in the room, without even trying.
Missy Elliott - A pioneer of late '90s and early 2000s hip hop, Missy Elliott set the standards for street fashion for her time. The 'Supa Dupa Fly' artist truly was, and remains, exactly that.
Bruce Springsteen - The hero of the working class, Bruce Springsteen has always dressed the part, with his ripped sleeveless shirts, denim, and his now-iconic red headband.
Erykah Badu - Erykah Badu always had a flair for grandiose, consistently rocking oversized hats and hair wraps with ease and finesse.
Elton John - One of the most legendary figures in the history of music, Elton John has never shied away from loud and bombastic looks throughout his career.
Madonna - Madonna has inspired multiple generations of people around the world with her ever-evolving kaleidoscopic looks.
Chet Baker - Chet Baker was always dressed in sleek, simple suits that defined the jazz styles of his day.
Elvis Costello - Elvis Costello has always walked the fine and stylish line between sleek and street smart.