The 16 Most Stylish Musicians of the Last 50 Years

The men, anyway, according to one of the Internet’s ultimate arbiters of cool BY SEAN SULLIVAN

 1  2

Bob Dylan
Blood on the Tracks, Blonde on Blonde,, suede and stripes: The man can do no wrong.
FIONA ADAMS/GETTY

Jack White
Red-and-white, black-on-black, hand-on-guitar: The man looks damn good doing what he does.
STEPHEN LOVEKIN/WIREIMAGE

 3  4

Bob Marley
M-65 jackets, Adidas track suits, chinos: The man was hard not to love.
MAURICE HIBBERD/GETTY

Gregory Isaacs
The original cool ruler.
EBET ROBERTS/GETTY

 5  6

Serge Gainsbourg
The original enfant terrible.
KEYSTONE-FRANCE/GETTY

Johnny Cash
The original man in black, and the only one.
MICHAEL OCHS ARCHIVES/GETTY

 7  8

David Bowie
“Don’t fight the urge to tone down your look as you grow.”
ORION PICTURES CORP/EVERETT COLLECTION

George Harrison
Now that is a look.
JUERGEN VOLLMER/GETTY

 9  10

Andre 3000
“Anybody can wear crazy clothes and anybody can wear classic clothes. Balancing the two can be an art.”
LORENZO BRINGHELI

Pete Doherty
If for no other reason than his unwavering endorsement of headwear.
TIM WHITBY/GETTY

 11  12

Marvin Gaye
There is so much style on the cover of What’s Going On that it hurts.
GETTY / ECHOES/GETTY

Keith Richards
This man is wearing a leopard jacket.
KEYSTONE-FRANCE/GET

 13  14

Mick Jagger
Sex, drugs, rock ‘n’ roll, and polka-dot scarves.
CONTRASTO

Charlie Watts
During the mid-’80s, in the middle of the night, an intoxicated Jagger phoned up Watts’s hotel room and asked, “Where’s my drummer?” Watts got up, shaved, put on a suit, tie, and freshly shined shoes, walked down the stairs, punched Jagger in the face, and said, “Don’t ever call me your drummer again. You’re my fucking singer!”
CHRISTOPHER SIMON SYKES/GETTY

 15  18

Bryan Ferry
Again with the polka-dot scarf — a bit silkier, but all smooth.
GIJSBERT HANEKROOT/GETTY

Brandon Flowers
The Killers lead singer gave bartenders the panache, from 2007 to present, to refer to themselves as “mixologists.”
VICTOR CHAVEZ/GETTY

 16  17

Run DMC
Kangol hat, track suit, white-and-black Superstars. Game over. Nothing was ever the same.
MICHAEL OCHS ARCHIVES/GETTY

The Ramones
You could line up four pairs of trashed jeans and four Schott Perfectos and any rightful music fan walking by would mouth the same thing: “Joey, Johnny, Dee Dee, and Tommy.”
MICHAEL OCHS ARCHIVES/GETTY

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