The 23 Best Golden Globes Beauty Looks of All Time

Since the first ceremony in 1944, the Golden Globe Awards have become a night for Hollywood to hang loose—a chance for television and film stars to hit the red carpet together, sporting expressive hair and makeup that, looking back, has become a benchmark of beauty by the decade.

See the ’70s glamour of Anjelica Huston, a white flower pinned into her dark hair and a young Jack Nicholson in tow, or Drew Barrymore fearlessly defining the ’90s with a flipped bob and pencil-thin brows. Unlike at the Oscars, there’s no playing it safe—and that has made the Globes all the more compelling.

From Grace Kelly’s sleek '50s bun to Lupita Nyong'o's ethereal skin, here are 23 standout looks that prove why risk-taking beauty is timeless.

Grace Kelly, 1956

Grace Kelly, 1956

Grace Kelly, 1956
Photo: Getty Images
Elizabeth Taylor, 1958

Elizabeth Taylor, 1958

Elizabeth Taylor, 1958
Photo: Getty Images
Marilyn Monroe (with José Bolaños), 1962

Marilyn Monroe (with José Bolaños), 1962

Marilyn Monroe (with José Bolaños), 1962
Photo: Getty Images
Mia Farrow (with Leonard Gershe), 1966

Mia Farrow (with Leonard Gershe), 1966

Mia Farrow (with Leonard Gershe), 1966
Photo: Getty Images
Cher (with Sonny Bono), 1973

Cher (with Sonny Bono), 1973

Cher (with Sonny Bono), 1973
Photo: Getty Images
Anjelica Huston (with Jack Nicholson), 1974

Anjelica Huston (with Jack Nicholson), 1974

Anjelica Huston (with Jack Nicholson), 1974
Photo: Getty Images
Julia Roberts, 1991

Julia Roberts, 1991

Julia Roberts, 1991
Photo: Getty Images
Drew Barrymore, 1993

Drew Barrymore, 1993

Drew Barrymore, 1993
Photo: Getty Images
Winona Ryder, 1994

Winona Ryder, 1994

Winona Ryder, 1994
Photo: Getty Images
Kate Moss (with Johnny Depp), 1995

Kate Moss (with Johnny Depp), 1995

Kate Moss (with Johnny Depp), 1995
Photo: Getty Images
Uma Thurman, 1995

Uma Thurman, 1995

Uma Thurman, 1995
Photo: Getty Images
Angelina Jolie (with Jonny Lee Miller), 1999

Angelina Jolie Pitt (with Jonny Lee Miller), 1999

Angelina Jolie (with Jonny Lee Miller), 1999
Photo: Getty Images
Gwyneth Paltrow, 1999

Gwyneth Paltrow, 1999

Gwyneth Paltrow, 1999
Photo: Getty Images
Halle Berry, 2000

Halle Berry, 2000

Halle Berry, 2000
Photo: Corbis
Sienna Miller, 2007

Sienna Miller, 2007

Sienna Miller, 2007
Photo: Getty Images
Marion Cotillard, 2010

Marion Cotillard, 2010

Marion Cotillard, 2010
Photo: Getty Images
Rooney Mara, 2012

Rooney Mara, 2012

Rooney Mara, 2012
Photo: Getty Images
Beyoncé, 2007

Beyoncé, 2007

Beyoncé, 2007
Photo: Corbis
Natalie Portman, 2011

Natalie Portman, 2011

Natalie Portman, 2011
Photo: Corbis
Lupita Nyong’o, 2014

Lupita Nyong’o, 2014

Lupita Nyong’o, 2014
Photo: Getty Images
Emma Stone, 2015

Emma Stone, 2015

Emma Stone, 2015
Photo: Getty Images
Alicia Vikander, 2016

Alicia Vikander, 2016

Alicia Vikander, 2016
Photo: Getty Images
Michelle Williams, 2017

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Michelle Williams, 2017
Photo: Getty Images
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Frazer Harrison

Gemma Chan, 2019

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Originally Appeared on Vogue