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
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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
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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
1 of 50
David Bowie
"Don't fight the urge to tone down your look as you grow."
Getty Images
2 of 50
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
3 of 50
The Beastie Boys
Take a walk down to your local sneakerhead store and take a look around at the Beastie Boys.
Getty Images
4 of 50
Advertisement
Brandon Flowers
The Killers lead singer gave bartenders the panache, from 2007 to present, to refer to themselves as "mixologists."
Getty Images
5 of 50
Serge Gainsbourg
The original enfant terrible.
Getty Images
6 of 50
The Velvet Underground
Because Lou Reed, that's why.
Getty Images
7 of 50
Chet Baker
Master of the white t-shirt.
Getty Images
8 of 50
Advertisement
George Harrison
Now that is a look.
Getty Images
9 of 50
Andre 3000
"Anybody can wear crazy clothes and anybody can wear classic clothes. Balancing the two can be an art."
Lorenzo Bringheli
10 of 50
The Smiths
Even without Morrissey.
Stephen Wright/Getty
11 of 50
Mick Jagger
Sex, drugs, rock 'n' roll, and polka-dot scarves.
Contrasto
12 of 50
Advertisement
Bob Marley
M-65 jackets, Adidas track suits, chinos: The man was hard not to love.
Getty Images
13 of 50
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
14 of 50
Miles Davis
Miles Davis.
Getty Images
15 of 50
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
16 of 50
Advertisement
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
17 of 50
Run DMC
Kangol hat, track suit, white-and-black Superstars. Game over. Nothing was ever the same.
Getty Images
18 of 50
Tom Waits
See left.
Getty Images
19 of 50
Pete Doherty
If for no other reason than his unwavering endorsement of headwear.
Getty Images
20 of 50
Advertisement
Jack White
Red-and-white, black-on-black, hand-on-guitar: The man looks damn good doing what he does.
Getty Images
21 of 50
Jay-Z
"The king of what? The king of styyyle." —Style Wars
Getty Images
22 of 50
Elvis Costello
Gave members of the A/V club the right to wear Coke-bottle glasses, forever.
Getty Images
23 of 50
Marvin Gaye
There is so much style on the cover of What's Going On that it hurts.
Getty Images
24 of 50
Advertisement
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
25 of 50
Bob Dylan
Blood on the Tracks, Blonde on Blonde, suede and stripes: The man can do no wrong.
Getty Images
26 of 50
Keith Richards
This man is wearing a leopard jacket.
Getty Images
27 of 50
Elvis Presley
The King was comfortable in stripes-over-stripes. Automatic pass.
Getty Images
28 of 50
Advertisement
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
29 of 50
Gregory Isaacs
The original cool ruler.
Getty Images
30 of 50
Johnny Rotten
Who else could make a striped mohair sweater a punk thing?
Express/Getty
31 of 50
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
32 of 50
Advertisement
Mos Def
Never saw a bold pattern that scared him.
Andrew Kent/Getty
33 of 50
Ray Charles
"I never wanted to be famous. I only wanted to be great."
Gamma-Rapho/Getty
34 of 50
Jarvis Cocker
Pulp's master of Britpop wore suits when he didn't have to. Now everyone has to.
Mick Hutson/Getty
35 of 50
Morrissey
That hair, man. That hair.
Patti Ouderkirk/WireImage
36 of 50
Advertisement
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
37 of 50
Daft Punk
Because helmets.
Eric Charbonneau/WireImage
38 of 50
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
39 of 50
Johnny Cash
The original man in black, and the only one.
Michael Ochs Archives/Getty
40 of 50
Advertisement
Ian Curtis
Joy Division's master of Manchester post-punk did the dark trench right. Really right.
Kevin Cummins/Getty
41 of 50
Bruce Springsteen
The master of Jersey rebel style does everything right, one faded leather jacket at a time.
Michael Ochs Archives/Getty
42 of 50
U.S. Royalty
These up-and-comers bring a hint of history — and a healthy dose of style — to the Beltway...
Aaron Stern
43 of 50
Eric Clapton
...and this is where they got it from.
Jan Persson/Getty
44 of 50
Advertisement
Jimi Hendrix
No one did psychedelic better, onstage or off.
Bruce Fleming/Getty
45 of 50
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."
46 of 50
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
47 of 50
Frank Sinatra
The Chairman of the Board: always proper, always drink in hand.
David Redfern/Redferns
48 of 50
Advertisement
Iggy Pop
Anyone who can make chest scars and faded Levi's a thing is alright in my book.
David Corio/Getty
49 of 50
John Lennon
Period.
Tom Hanley/Getty
50 of 50
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