Celebrity Transformations Madonna's Changing Looks By InStyle Editors InStyle Editors Instagram Twitter InStyle's mantra is "Everybody's in," and that means anyone who finds their way to our stories should find themselves reflected in them. We prioritize bringing the right writer to every story and sometimes collaborate as a team to ensure we're including points of view across race, gender expression, body size, skin and hair type, and more. Our editors and writers comprise decades of expertise across the beauty, fashion, lifestyle and wellness spaces in print and digital. We prioritize journalistic integrity, factual accuracy, and also having fun with every story we share. For more about our team, click here. InStyle's editorial guidelines Updated on August 12, 2014 Pin Share Tweet Email Photo: Taylor Hill/FilmMagic Madonna's Changing Looks 01 of 23 1975 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 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 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 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 Retna 5/Retna Her album Like a Virgin sold millions of copies, but her look was pure D.I.Y. 06 of 23 1985 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 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 Starstock/Photoshot/Everett Collection She channeled a geisha for the Cannes Film Festival premiere of Madonna: Truth or Dare. 09 of 23 1995 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 S. Granitz/WireImage Madonna went au naturel for an Evita screening with soft wheat-blond curls and understated makeup. 11 of 23 1998 Ke.Mazur/WireImage Dark, dramatic red lips and hair for the launch of Ray of Light. 12 of 23 2000 Gregg DeGuire/WireImage For the launch of Music, Madonna chose candy-colored purple shadow and patent fuchsia lips. 13 of 23 2003 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 Evan Agostini/Getty Images Madonna went disco for Confessions on a Dance Floor with feathered locks and sparkling shadow. 15 of 23 2007 Tony Barson/WireImage She hit the post-Oscars parties with Marilyn waves and pretty peach lips. 16 of 23 2008 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 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 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 Steve Granitz/WireImage "Madonna wanted easy natural texture hair," Wella Professionals hairstylist Andy LeCompte said of her Globes look. 20 of 23 2013 Jeffrey Mayer/WireImage The icon goes for a faux bob, keeping her signature blonde hairdo. 21 of 23 2014 Jon Kopaloff/FilmMagic Madonna opts for a black hat and accompanying grill (not pictured). 22 of 23 2015 Jon Kopaloff/FilmMagic At the Grammys, Madonna channeled a matador for her red carpet and on-stage outfits. 23 of 23 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. Was this page helpful? Thanks for your feedback! Tell us why! Other Submit