
Style
The 50 Most Stylish Musicians Of The Last 50 Years
From the Stones to the Smiths to Biggie Smalls.
BY sean sullivan | Jul 24, 2018 | Fashion

Musicians may get famous for their, well, music, but their senses of style are another iconic part of their personas and performances. Here, a look back at some of the most stylish music men of the past 50 years. They do not disappoint.
From: Esquire US

Bryan Ferry
Again with the polka-dot scarf — a bit silkier, but all smooth.
Getty Images

David Bowie
"Don't fight the urge to tone down your look as you grow."
Getty Images

Interpol
A killer suit selection will always land you on a "best-dressed" list. That and an album as audibly stylish as Turn on the Bright Lights.
Getty Images

The Beastie Boys
Take a walk down to your local sneakerhead store and take a look around at the Beastie Boys.
Getty Images

Brandon Flowers
The Killers lead singer gave bartenders the panache, from 2007 to present, to refer to themselves as "mixologists."
Getty Images

Serge Gainsbourg
The original enfant terrible.
Getty Images

The Velvet Underground
Because Lou Reed, that's why.
Getty Images

Chet Baker
Master of the white t-shirt.
Getty Images

George Harrison
Now that is a look.
Getty Images

Andre 3000
"Anybody can wear crazy clothes and anybody can wear classic clothes. Balancing the two can be an art."
Lorenzo Bringheli

The Smiths
Even without Morrissey.
Stephen Wright/Getty

Mick Jagger
Sex, drugs, rock 'n' roll, and polka-dot scarves.
Contrasto

Bob Marley
M-65 jackets, Adidas track suits, chinos: The man was hard not to love.
Getty Images

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!"
Getty Images

Miles Davis
Miles Davis.
Getty Images

Bo Diddley
"I was out to destroy the audience. I wanted to destroy 'em, just make the toughest dude in the crowd pat his foot. I'd find a groove to get 'em by watching feet, and once I got one guy moving, I'd start working on the dude sitting next to him."
Getty Images

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."
Getty Images

Run DMC
Kangol hat, track suit, white-and-black Superstars. Game over. Nothing was ever the same.
Getty Images

Tom Waits
See left.
Getty Images

Pete Doherty
If for no other reason than his unwavering endorsement of headwear.
Getty Images

Jack White
Red-and-white, black-on-black, hand-on-guitar: The man looks damn good doing what he does.
Getty Images

Jay-Z
"The king of what? The king of styyyle." —Style Wars
Getty Images

Elvis Costello
Gave members of the A/V club the right to wear Coke-bottle glasses, forever.
Getty Images

Marvin Gaye
There is so much style on the cover of What's Going On that it hurts.
Getty Images

The Specials
Take a look at the first family of ska — all skinny ties and stingy brims — before trying on that pork-pie hat this summer. No one has done it right since.
Getty Images

Bob Dylan
Blood on the Tracks, Blonde on Blonde, suede and stripes: The man can do no wrong.
Getty Images

Keith Richards
This man is wearing a leopard jacket.
Getty Images

Elvis Presley
The King was comfortable in stripes-over-stripes. Automatic pass.
Getty Images

Biggie Smalls
Because you may have not been wearing a Coogi sweater or a Jacob the Jeweler watch to sixth-period study hall, but Biggie definitely put that swagger in your step through those headphones.
Getty Images

Gregory Isaacs
The original cool ruler.
Getty Images

Johnny Rotten
Who else could make a striped mohair sweater a punk thing?
Express/Getty

David Bryne
The big-shouldered jackets didn't come until later. And it was the '80s. Everyone was doing it. It was just... around.
Michael Ochs Archives/Getty

Mos Def
Never saw a bold pattern that scared him.
Andrew Kent/Getty

Ray Charles
"I never wanted to be famous. I only wanted to be great."
Gamma-Rapho/Getty

Jarvis Cocker
Pulp's master of Britpop wore suits when he didn't have to. Now everyone has to.
Mick Hutson/Getty

Morrissey
That hair, man. That hair.
Patti Ouderkirk/WireImage

Jim James
Because they all wear the long hair and the beard these days, but thank god the My Morning Jacket frontman is making them wear tailored suits again, too.
C Flanigan/Getty

Daft Punk
Because helmets.
Eric Charbonneau/WireImage

Albert Hammond Jr.
The Strokes guitarist helped usher back in the age of the skinny suit. Tailors across New York licked their chops.
J. Shearer/Getty

Johnny Cash
The original man in black, and the only one.
Michael Ochs Archives/Getty

Ian Curtis
Joy Division's master of Manchester post-punk did the dark trench right. Really right.
Kevin Cummins/Getty

Bruce Springsteen
The master of Jersey rebel style does everything right, one faded leather jacket at a time.
Michael Ochs Archives/Getty

U.S. Royalty
These up-and-comers bring a hint of history — and a healthy dose of style — to the Beltway...
Aaron Stern

Eric Clapton
...and this is where they got it from.
Jan Persson/Getty

Jimi Hendrix
No one did psychedelic better, onstage or off.
Bruce Fleming/Getty

The Band
Robbie Robertson: "When we were working with Bob Dylan and we moved to Woodstock, everybody referred to us as the band. He called us the band, our friends called us the band, our neighbors called us the band."
Richard Manuel: "We started out with The Crackers. We tried to call ourselves The Honkies. Everybody kind of backed off from that. It was too straight. So we decided just to call ourselves... The Band."

Thelonius Monk
He could pull off two looks — squash glasses and stingy brim hats — with extreme ease. A feat not for everyone.
Gilles Petard/Getty

Frank Sinatra
The Chairman of the Board: always proper, always drink in hand.
David Redfern/Redferns

Iggy Pop
Anyone who can make chest scars and faded Levi's a thing is alright in my book.
David Corio/Getty

John Lennon
Period.
Tom Hanley/Getty

Bryan Ferry
Again with the polka-dot scarf — a bit silkier, but all smooth.
Getty Images

David Bowie
"Don't fight the urge to tone down your look as you grow."
Getty Images

Interpol
A killer suit selection will always land you on a "best-dressed" list. That and an album as audibly stylish as Turn on the Bright Lights.
Getty Images

The Beastie Boys
Take a walk down to your local sneakerhead store and take a look around at the Beastie Boys.
Getty Images

Brandon Flowers
The Killers lead singer gave bartenders the panache, from 2007 to present, to refer to themselves as "mixologists."
Getty Images

Serge Gainsbourg
The original enfant terrible.
Getty Images

The Velvet Underground
Because Lou Reed, that's why.
Getty Images

Chet Baker
Master of the white t-shirt.
Getty Images

George Harrison
Now that is a look.
Getty Images

Andre 3000
"Anybody can wear crazy clothes and anybody can wear classic clothes. Balancing the two can be an art."
Lorenzo Bringheli

The Smiths
Even without Morrissey.
Stephen Wright/Getty

Mick Jagger
Sex, drugs, rock 'n' roll, and polka-dot scarves.
Contrasto

Bob Marley
M-65 jackets, Adidas track suits, chinos: The man was hard not to love.
Getty Images

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!"
Getty Images

Miles Davis
Miles Davis.
Getty Images

Bo Diddley
"I was out to destroy the audience. I wanted to destroy 'em, just make the toughest dude in the crowd pat his foot. I'd find a groove to get 'em by watching feet, and once I got one guy moving, I'd start working on the dude sitting next to him."
Getty Images

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."
Getty Images

Run DMC
Kangol hat, track suit, white-and-black Superstars. Game over. Nothing was ever the same.
Getty Images

Tom Waits
See left.
Getty Images

Pete Doherty
If for no other reason than his unwavering endorsement of headwear.
Getty Images

Jack White
Red-and-white, black-on-black, hand-on-guitar: The man looks damn good doing what he does.
Getty Images

Jay-Z
"The king of what? The king of styyyle." —Style Wars
Getty Images

Elvis Costello
Gave members of the A/V club the right to wear Coke-bottle glasses, forever.
Getty Images

Marvin Gaye
There is so much style on the cover of What's Going On that it hurts.
Getty Images

The Specials
Take a look at the first family of ska — all skinny ties and stingy brims — before trying on that pork-pie hat this summer. No one has done it right since.
Getty Images

Bob Dylan
Blood on the Tracks, Blonde on Blonde, suede and stripes: The man can do no wrong.
Getty Images

Keith Richards
This man is wearing a leopard jacket.
Getty Images

Elvis Presley
The King was comfortable in stripes-over-stripes. Automatic pass.
Getty Images

Biggie Smalls
Because you may have not been wearing a Coogi sweater or a Jacob the Jeweler watch to sixth-period study hall, but Biggie definitely put that swagger in your step through those headphones.
Getty Images

Gregory Isaacs
The original cool ruler.
Getty Images

Johnny Rotten
Who else could make a striped mohair sweater a punk thing?
Express/Getty

David Bryne
The big-shouldered jackets didn't come until later. And it was the '80s. Everyone was doing it. It was just... around.
Michael Ochs Archives/Getty

Mos Def
Never saw a bold pattern that scared him.
Andrew Kent/Getty

Ray Charles
"I never wanted to be famous. I only wanted to be great."
Gamma-Rapho/Getty

Jarvis Cocker
Pulp's master of Britpop wore suits when he didn't have to. Now everyone has to.
Mick Hutson/Getty

Morrissey
That hair, man. That hair.
Patti Ouderkirk/WireImage

Jim James
Because they all wear the long hair and the beard these days, but thank god the My Morning Jacket frontman is making them wear tailored suits again, too.
C Flanigan/Getty

Daft Punk
Because helmets.
Eric Charbonneau/WireImage

Albert Hammond Jr.
The Strokes guitarist helped usher back in the age of the skinny suit. Tailors across New York licked their chops.
J. Shearer/Getty

Johnny Cash
The original man in black, and the only one.
Michael Ochs Archives/Getty

Ian Curtis
Joy Division's master of Manchester post-punk did the dark trench right. Really right.
Kevin Cummins/Getty

Bruce Springsteen
The master of Jersey rebel style does everything right, one faded leather jacket at a time.
Michael Ochs Archives/Getty

U.S. Royalty
These up-and-comers bring a hint of history — and a healthy dose of style — to the Beltway...
Aaron Stern

Eric Clapton
...and this is where they got it from.
Jan Persson/Getty

Jimi Hendrix
No one did psychedelic better, onstage or off.
Bruce Fleming/Getty

The Band
Robbie Robertson: "When we were working with Bob Dylan and we moved to Woodstock, everybody referred to us as the band. He called us the band, our friends called us the band, our neighbors called us the band."
Richard Manuel: "We started out with The Crackers. We tried to call ourselves The Honkies. Everybody kind of backed off from that. It was too straight. So we decided just to call ourselves... The Band."

Thelonius Monk
He could pull off two looks — squash glasses and stingy brim hats — with extreme ease. A feat not for everyone.
Gilles Petard/Getty

Frank Sinatra
The Chairman of the Board: always proper, always drink in hand.
David Redfern/Redferns

Iggy Pop
Anyone who can make chest scars and faded Levi's a thing is alright in my book.
David Corio/Getty

John Lennon
Period.
Tom Hanley/Getty
COMMENTS