Madonna's Changing Looks

2016
Photo: Taylor Hill/FilmMagic

Madonna's Changing Looks

01 of 23

1975

Madonna - Transformation - Beauty
Seth Poppel/Yearbook Library

The Rochester Adams High School cheerleader plucked her brows pencil-thin and played up her eyes with soft liner.

02 of 23

1978

Madonna - Transformation - Beauty
Michael McDonnell/Hulton Archive/Getty Images

For her acting headshot, the new New Yorker sported wild crimped hair and wispy bangs.

03 of 23

1979

Madonna - Transformation - Beauty
Michael McDonnell/Hulton Archive/Getty Images

Madonna goes punk: the Manhattan scenester rocked a gelled crop, heavy lipstick and artfully applied shadow.

04 of 23

1983

Madonna - Transformation - Beauty
Michael Putland/Retna

She released her self-titled debut album and brought downtown N.Y.C. club style to the masses.

05 of 23

1984

Madonna - Transformation - Beauty
Retna 5/Retna

Her album Like a Virgin sold millions of copies, but her look was pure D.I.Y.

06 of 23

1985

Madonna - Transformation - Beauty
Ron Galella/WireImage

"This was the Like a Virgin era," makeup artist Gina Brooke has said of Madonna's American Music Awards look. "She laughs about how she did her own makeup."

07 of 23

1987

Madonna - Transformation - Beauty
Ron Galella/WireImage

"The red lips and beauty mark were her signature at the time," Brooke said of Madge's take on Marilyn. Messy platinum waves and unkempt brows completed the Who's That Girl look.

08 of 23

1991

Madonna - Transformation - Beauty
Starstock/Photoshot/Everett Collection

She channeled a geisha for the Cannes Film Festival premiere of Madonna: Truth or Dare.

09 of 23

1995

Madonna - Transformation - Beauty
Ron Galella/WireImage

For the MTV Video Music Awards, the Bedtime Stories singer got inspired by another beauty icon. "This is very Catherine Deneuve in Belle de Jour-big hair with lots of teasing," said hairstylist Garren.

10 of 23

1996

Madonna - Transformation - Beauty
S. Granitz/WireImage

Madonna went au naturel for an Evita screening with soft wheat-blond curls and understated makeup.

11 of 23

1998

Madonna - Transformation - Beauty
Ke.Mazur/WireImage

Dark, dramatic red lips and hair for the launch of Ray of Light.

12 of 23

2000

Madonna - Transformation - Beauty
Gregg DeGuire/WireImage

For the launch of Music, Madonna chose candy-colored purple shadow and patent fuchsia lips.

13 of 23

2003

Madonna - Transformation - Beauty
Matt Baron/BEImages

She debuted her first children's book and took on a mature new look. "Her eyes are her best feature," says Brooke. "She has fun playing them up with liquid liner."

14 of 23

2005

Madonna - Transformation - Beauty
Evan Agostini/Getty Images

Madonna went disco for Confessions on a Dance Floor with feathered locks and sparkling shadow.

15 of 23

2007

Madonna - Transformation - Beauty
Tony Barson/WireImage

She hit the post-Oscars parties with Marilyn waves and pretty peach lips.

16 of 23

2008

Madonna - Transformation - Beauty
Daniele Venturelli/WireImage

Madonna celebrated a milestone birthday and released her 11th album, Hard Candy. "At 50, she's even more experimental," says Brooke.

17 of 23

2009

Madonna - Transformation - Beauty
Frank Micelotta/Getty Images

The icon inspired again with the dramatic looks for her "Sticky and Sweet" tour. "She doesn't take on trends, she creates them," says hairstylist Andy LeCompte. "That's why she likes taking risks."

18 of 23

2010

Madonna - Transformation - Beauty
Dimitrios Kambouris/WireImage

Madonna went soft for an N.Y.C. benefit with retro waves, mega lashes and barely-there makeup.

19 of 23

2012

Madonna - Transformation - Hair - Celebrity Before and After
Steve Granitz/WireImage

"Madonna wanted easy natural texture hair," Wella Professionals hairstylist Andy LeCompte said of her Globes look.

20 of 23

2013

2013 Billboard Music Awards - Press Room
Jeffrey Mayer/WireImage

The icon goes for a faux bob, keeping her signature blonde hairdo.

21 of 23

2014

56th GRAMMY Awards - Arrivals
Jon Kopaloff/FilmMagic

Madonna opts for a black hat and accompanying grill (not pictured).

22 of 23

2015

57th GRAMMY Awards - Arrivals
Jon Kopaloff/FilmMagic

At the Grammys, Madonna channeled a matador for her red carpet and on-stage outfits.

23 of 23

2016

2016
Taylor Hill/FilmMagic

At the 2016 Met Gala, the 57-year-old star chose loose waves and a jeweled headpiece to accompany her racy cutout dress.

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