Cool Stuff

The 100 Most Stylish Men Ever

As we like to repeat to ourselves every morning as we stare at our reflection in the mirror, fashion is temporary, style is timeless.

But style is often in the eye of the beholder. What works for one man, might make another chap look like a right twazzock. So, who to emulate? And why?

We've assembled a list of the 100 most stylish men ever to give us all a bit of inspiration.

(Images: Rex Features)

  • Alan Delon

    Alan Delon

    More details

    Alan Delon

    Alan Delon

  • Albert Hammond Jr

    Albert Hammond Jr

    More details

    Albert Hammond Jr

    Albert Hammond Jr

  • Woody Allen

    Woody Allen

    More details

    Woody Allen

    Woody Allen

  • Jean-Paul Belmondo

    Jean-Paul Belmondo

    More details

    Jean-Paul Belmondo

    Jean-Paul Belmondo

  • David Bowie

    David Bowie

    More details

    David Bowie

    David Bowie

  • Brad Pitt

    Brad Pitt

    More details

    Brad Pitt

    Brad Pitt

  • Burt Reynolds

    Burt Reynolds

    More details

    Burt Reynolds

    Burt Reynolds

  • David Burne

    David Burne

    More details

    David Burne

    David Burne

  • Cary Grant

    Cary Grant

    More details

    Cary Grant

    Cary Grant

  • Clint Eastwood

    Clint Eastwood

    More details

    Clint Eastwood

    Clint Eastwood

  • David Beckham

    David Beckham

    More details

    David Beckham

    David Beckham

  • David Lynch

    David Lynch

    More details

    David Lynch

    David Lynch

  • Elvis

    Elvis

    More details

    Elvis

    Elvis

  • Gregory Peck

    Gregory Peck

    More details

    Gregory Peck

    Gregory Peck

  • James Dean

    James Dean

    More details

    James Dean

    James Dean

  • Jarvis Cocker

    Jarvis Cocker

    More details

    Jarvis Cocker

    Jarvis Cocker

  • Jimi Hendrix

    Jimi Hendrix

    More details

    Jimi Hendrix

    Jimi Hendrix

  • John Cussack

    John Cussack

    More details

    John Cussack

    John Cussack

  • John Lennon

    John Lennon

    More details

    John Lennon

    John Lennon

  • Johnny Depp

    Johnny Depp

    More details

    Johnny Depp

    Johnny Depp

  • Jon Hamm

    Jon Hamm

    More details

    Jon Hamm

    Jon Hamm

  • Jon Snow

    Jon Snow

    More details

    Jon Snow

    Jon Snow

  • Julian Casablancas

    Julian Casablancas

    More details

    Julian Casablancas

    Julian Casablancas

  • Kanye West

    Kanye West

    More details

    Kanye West

    Kanye West

  • Keith Floyd

    Keith Floyd

    More details

    Keith Floyd

    Keith Floyd

  • Lemmy

    Lemmy

    More details

    Lemmy

    Lemmy

  • Malcolm X

    Malcolm X

    More details

    Malcolm X

    Malcolm X

  • Marlon Brando

    Marlon Brando

    More details

    Marlon Brando

    Marlon Brando

  • Michael Caine

    Michael Caine

    More details

    Michael Caine

    Michael Caine

  • Morrissey

    Morrissey

    More details

    Morrissey

    Morrissey

  • Mr T
    Mr T

    Mr T

  • Patrick Grant

    Patrick Grant

    More details

    Patrick Grant

    Patrick Grant

  • Paul Weller

    Paul Weller

    More details

    Paul Weller

    Paul Weller

  • Robert Downey Jr

    Robert Downey Jr

    More details

    Robert Downey Jr

    Robert Downey Jr

  • Robert Redford

    Robert Redford

    More details

    Robert Redford

    Robert Redford

  • Ronnie Wood

    Ronnie Wood

    More details

    Ronnie Wood

    Ronnie Wood

  • Ryan Gosling

    Ryan Gosling

    More details

    Ryan Gosling

    Ryan Gosling

  • Tinie Tempah

    Tinie Tempah

    More details

    Tinie Tempah

    Tinie Tempah

  • Samuel Beckett

    Samuel Beckett

    More details

    Samuel Beckett

    Samuel Beckett

  • Sean Connery

    Sean Connery

    More details

    Sean Connery

    Sean Connery

  • Serge Gainsbourg

    Serge Gainsbourg

    More details

    Serge Gainsbourg

    Serge Gainsbourg

  • Steve McQueen

    Steve McQueen

    More details

    Steve McQueen

    Steve McQueen

  • Tin Tin

    Tin Tin

    More details

    Tin Tin

    Tin Tin

  • Tom Ford

    Tom Ford

    More details

    Tom Ford

    Tom Ford

  • Tom Selleck

    Tom Selleck

    More details

    Tom Selleck

    Tom Selleck

  • Tom Waits

    Tom Waits

    More details

    Tom Waits

    Tom Waits

  • Vincent Cassell

    Vincent Cassell

    More details

    Vincent Cassell

    Vincent Cassell

  • Warren Beatty

    Warren Beatty

    More details

    Warren Beatty

    Warren Beatty

  • George Best

    George Best

    More details

    George Best

    George Best

  • Pep Guardiola

    Pep Guardiola

    More details

    Pep Guardiola

    Pep Guardiola

  • Adrien Brody

    Adrien Brody

    More details

    Adrien Brody

    Adrien Brody

  • Al Pacino

    Al Pacino

    More details

    Al Pacino

    Al Pacino

  • Albert Finney

    Albert Finney

    More details

    Albert Finney

    Albert Finney

  • Alex Turner

    Alex Turner

    More details

    Alex Turner

    Alex Turner

  • Andy Warhol

    Andy Warhol

    More details

    Andy Warhol

    Andy Warhol

  • Barack Obama

    Barack Obama

    More details

    Barack Obama

    Barack Obama

  • Bob Dylan

    Bob Dylan

    More details

    Bob Dylan

    Bob Dylan

  • Clark Gable

    Clark Gable

    More details

    Clark Gable

    Clark Gable

  • Clive Owen

    Clive Owen

    More details

    Clive Owen

    Clive Owen

  • Daniel Craig

    Daniel Craig

    More details

    Daniel Craig

    Daniel Craig

  • David Hemmings

    David Hemmings

    More details

    David Hemmings

    David Hemmings

  • Dean Martin

    Dean Martin

    More details

    Dean Martin

    Dean Martin

  • Errol Flynn

    Errol Flynn

    More details

    Errol Flynn

    Errol Flynn

  • Frank Sinatra

    Frank Sinatra

    More details

    Frank Sinatra

    Frank Sinatra

  • James Brown

    James Brown

    More details

    James Brown

    James Brown

  • James Corburn

    James Corburn

    More details

    James Corburn

    James Corburn

  • Jay-Z

    Jay-Z

    More details

    Jay-Z

    Jay-Z

  • Jim Morrison

    Jim Morrison

    More details

    Jim Morrison

    Jim Morrison

  • Gary Oldman

    Gary Oldman

    More details

    Gary Oldman

    Gary Oldman

  • Jude Law

    Jude Law

    More details

    Jude Law

    Jude Law

  • Paul Smith

    Paul Smith

    More details

    Paul Smith

    Paul Smith

  • Peter O'Toole

    Peter O'Toole

    More details

    Peter O'Toole

    Peter O'Toole

  • Pharrell Williams

    Pharrell Williams

    More details

    Pharrell Williams

    Pharrell Williams

  • Richard Burton

    Richard Burton

    More details

    Richard Burton

    Richard Burton

  • Richard Harris

    Richard Harris

    More details

    Richard Harris

    Richard Harris

  • Sam Riley

    Sam Riley

    More details

    Sam Riley

    Sam Riley

  • Terence Stamp

    Terence Stamp

    More details

    Terence Stamp

    Terence Stamp

  • Tim Roth

    Tim Roth

    More details

    Tim Roth

    Tim Roth

  • Kid Cudi

    Kid Cudi

    More details

    Kid Cudi

    Kid Cudi

  • Justin Timberlake

    Justin Timberlake

    More details

    Justin Timberlake

    Justin Timberlake

  • Mark Ronson

    Mark Ronson

    More details

    Mark Ronson

    Mark Ronson

  • Michael Jackson

    Michael Jackson

    More details

    Michael Jackson

    Michael Jackson

  • Montgomery Clift

    Montgomery Clift

    More details

    Montgomery Clift

    Montgomery Clift

  • Nick Cave

    Nick Cave

    More details

    Nick Cave

    Nick Cave

  • Paul Newman

    Paul Newman

    More details

    Paul Newman

    Paul Newman

  • Ewan McGregor

    Ewan McGregor

    More details

    Ewan McGregor

    Ewan McGregor

  • George Clooney

    George Clooney

    More details

    George Clooney

    George Clooney

  • Harrison Ford

    Harrison Ford

    More details

    Harrison Ford

    Harrison Ford

  • Jose Mourinho

    Jose Mourinho

    More details

    Jose Mourinho

    Jose Mourinho

  • Kurt Cobain

    Kurt Cobain

    More details

    Kurt Cobain

    Kurt Cobain

  • Liam Gallagher

    Liam Gallagher

    More details

    Liam Gallagher

    Liam Gallagher

  • Malcolm McDowell

    Malcolm McDowell

    More details

    Malcolm McDowell

    Malcolm McDowell

  • Marcello Mastroianni

    Marcello Mastroianni

    More details

    Marcello Mastroianni

    Marcello Mastroianni

  • Marc Jacobs

    Marc Jacobs

    More details

    Marc Jacobs

    Marc Jacobs

  • Matt Smith

    Matt Smith

    More details

    Matt Smith

    Matt Smith

  • Paul Simonon

    Paul Simonon

    More details

    Paul Simonon

    Paul Simonon

  • Peter Cook

    Peter Cook

    More details

    Peter Cook

    Peter Cook

  • Richard Ayoade

    Richard Ayoade

    More details

    Richard Ayoade

    Richard Ayoade

  • Robert De Niro

    Robert De Niro

    More details

    Robert De Niro

    Robert De Niro

  • Yves Saint Laurent

    Yves Saint Laurent

    More details

    Yves Saint Laurent

    Yves Saint Laurent

Tags: fashion, style

Share on

or email.

  • Facebook
  • Digg
  • Delicious

Add a comment

Follow Shortlist on Twitter

Ballot Box

Do you care about wearing designer labels?

Do you care about wearing designer labels?

Ballot Box

Which high-end piece of tech would you most like to buy?

Which high-end piece of tech would you most like to buy?

Ballot Box

Which sequel are you most looking forward to seeing?

Which sequel are you most looking forward to seeing?

Find Shortlist on Facebook