Madonna's Changing Looks

Photo: Taylor Hill/FilmMagic

Madonna's Changing Looks

01 of 23


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


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


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


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


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


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


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


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


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


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


Madonna - Transformation - Beauty

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

12 of 23


Madonna - Transformation - Beauty
Gregg DeGuire/WireImage

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

13 of 23


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


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


Madonna - Transformation - Beauty
Tony Barson/WireImage

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

16 of 23


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


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


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


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 Billboard Music Awards - Press Room
Jeffrey Mayer/WireImage

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

21 of 23


56th GRAMMY Awards - Arrivals
Jon Kopaloff/FilmMagic

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

22 of 23


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


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.

Related Articles