Prince exuded style everywhere he went. He began pushing the boundaries of what masculinity looked like from his very first record cover, and didn't stop until his dying day.
There is no denying that Canadian musician Grimes is one of the most stylish and unique music stars of today.
Janelle Monáe -
One of the 21st-century's most consistent icons of music and fashion, Janelle Monáe has challenged social norms throughout her career.
The Icelandic alien queen known as Björk stands in a league all her own.
David Bowie -
Few rock stars influenced fashion as much as David Bowie.
Siouxsie Sioux -
It's impossible to overstate Siouxsie Sioux's influence on music and fashion.
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.
Debbie Harry -
The American darling of new wave, Debbie Harry and her band Blondie were instrumental in the genesis of the musical genre and aesthetic that took a generation by storm.
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.
Stevie Wonder -
The prolific pioneer of a wide range of genres, from funk to soul to pop, is just as well known for his iconic braids-and-sunglasses look as he is for his contributions to music.
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.
James Brown -
Mr. Dynamite himself, James Brown was known as the "hardest working man in show business," and was also one of the best dressed.
Elvis Costello -
Elvis Costello has always walked the fine and stylish line between sleek and street smart.