Madonna's Changing Looks

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Seth Poppel/Yearbook Library

1. 1975

The Rochester Adams High School cheerleader plucked her brows pencil-thin and played up her eyes with soft liner.
Michael McDonnell/Hulton Archive/Getty Images

2. 1978

For her acting headshot, the new New Yorker sported wild crimped hair and wispy bangs.
Michael McDonnell/Hulton Archive/Getty Images

3. 1979

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

4. 1983

She released her self-titled debut album and brought downtown N.Y.C. club style to the masses.
Retna 5/Retna

5. 1984

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

6. 1985

"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."
Ron Galella/WireImage

7. 1987

"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.
Starstock/Photoshot/Everett Collection

8. 1991

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

9. 1995

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.
S. Granitz/WireImage

10. 1996

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

11. 1998

Dark, dramatic red lips and hair for the launch of Ray of Light.
Gregg DeGuire/WireImage

12. 2000

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

13. 2003

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."
Evan Agostini/Getty Images

14. 2005

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

15. 2007

She hit the post-Oscars parties with Marilyn waves and pretty peach lips.
Daniele Venturelli/WireImage

16. 2008

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

17. 2009

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."
Dimitrios Kambouris/WireImage

18. 2010

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

19. 2012

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

20. 2013

The icon goes for a faux bob, keeping her signature blonde hairdo.
Jon Kopaloff/FilmMagic

21. 2014

Madonna opts for a black hat and accompanying grill (not pictured).
Jon Kopaloff/FilmMagic

22. 2015

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

23. 2016

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

Madonna - Transformation - Beauty — Seth Poppel/Yearbook Library

1 of 23

1975

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

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