Drew Barrymore has been a Hollywood fixture since she was a kid, which means she grew up with plenty of eyes on her and her fashion choices.
As a child star in the ’80s, Barrymore was often seen in cute, frilly dresses with bows in her hair. By her teen years, she had started experimenting with her style. Skinny brows and super pale skin, which were both popular grunge-era trends, became somewhat of a signature makeup look for the star in the ’90s. She also had a penchant for wearing flowers in her hair (fitting since she ended up naming her beauty brand Flower).
As she moved into the 2000s, the “Ever After” actress adopted a slightly more refined wardrobe but kept her cool-girl vibe intact. She often opted for separates instead of dresses and wore of-the-time accessories like long skinny scarves.
More recently, Barrymore has upped the glam factor in her wardrobe, but still clearly likes experimenting with colors and silhouettes. One thing that’s remained relatively consistent over the past few years is the star’s hair. Along with whoever styles her locks, she has perfected effortless, beachy waves.
On Feb. 22, the “Never Been Kissed” star celebrates her 44th birthday. To celebrate her and her many style phases, check out the photos below:
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Drew Barrymore smiles with two front teeth missing.
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Barrymore with her half brother John Blyth Barrymore.
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Barrymore attends the Golden Globe Awards in Beverly Hills, California.
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Barrymore and her half brother John Blyth Barrymore.
Barrymore attends the Oscars.
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The actress wears a plaid dress and an animal purse.
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The actress at The China Club in New York City.
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Barrymore and Lynn Redgrave during the 1987 Aid for AIDS benefit gala at the Beverly Wilshire Hotel in Beverly Hills.
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Barrymore and Corey Feldman attend the 61st annual Academy Awards in Los Angeles.
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Barrymore wears a floral shirt and hoop earrings.
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Barrymore wears a leather jacket.
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The star at the premiere of “The Freshman” at the Coronet Theater in Westwood, California.
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Barrymore at the “Pacific Heights” premiere in Los Angeles.
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Barrymore attends the premiere of “Guilty By Suspicion” in Westwood.
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The actress attends the ”My Private Idaho” Los Angeles premiere at the Academy Theater in Beverly Hills.
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Barrymore and David Arquette attend the first annual Spago Christmas Party for Toys for Totskis Russian Airlift at Spago Restaurant in Hollywood.
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Barrymore and Jamie Walters attend the “Poison Ivy” premiere at the Cineplex Odeon Fairfax Theatre in West Hollywood.
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The star attends the “Silver” Los Angeles benefit premiere in Westwood.
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The actress attends the “Indiscretions” premiere after-party at Tavern on the Green in New York City.
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Barrymore and Eric Erlandson (of Hole) attend the premiere of “Batman Forever.”
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Barrymore wears a blonde wig and flowers in her hair at the 12th annual MTV Movie Awards.
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Barrymore attends the “Scream” London premiere.
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Barrymore attends the 70th annual Oscars in Los Angeles.
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Barrymore attends the “Wedding Singer” premiere in New York City.
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Barrymore arrives at the Teatro Odeon in Florence, Italy, for the “Ever After” premiere.
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Barrymore and Edward Norton attend the 71st annual Academy Awards in Los Angeles.
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The actress attends the 2000 NATO/Showest Convention in Las Vegas.
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Barrymore photographed with Tom Green at the “Titan A.E.” premiere in Los Angeles.
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Barrymore and Green at the premiere of “Charlie’s Angels” in Los Angeles.
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Lucy Liu, Barrymore and Cameron Diaz attend a special screening of “Charlie’s Angels” in New York.
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Barrymore poses at Nickelodeon’s 14th annual Kids’ Choice Awards in Santa Monica, California.
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Barrymore and Liu attend Premiere Magazine’s 8th annual Women in Hollywood Awards Lunch at the Four Seasons Hotel in Los Angeles.
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Barrymore attends the premiere of the 20th anniversary version of “E.T. The Extra-Terrestrial” in Los Angeles.
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Barrymore attends the “Confessions of a Dangerous Mind” premiere at the Mann Bruin Theatre in Westwood.
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The actress attends the 2003 Clive Davis Pre-Grammy Party in New York City.
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Diaz, Barrymore and Liu attend Nickelodeon’s 16th annual Kids’ Choice Awards in Santa Monica.
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Barrymore, Liu and Diaz attend the premiere of “Charlie’s Angels 2: Full Throttle” at Grauman’s Chinese Theatre in Hollywood.
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Barrymore arrives at the premiere of “50 First Dates” at the Mann Village in Westwood.
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The actress attends the 77th annual Academy Awards in Hollywood.
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Barrymore attends the Metropolitan Museum of Art’s Costume Institute Benefit Gala: Anglomania in New York City.
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Barrymore arrives at the 64th annual Golden Globe Awards in Beverly Hills.
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The star arrives at the world premiere of “Music and Lyrics” in London.
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The actress arrives at the Madonna + Gucci Present a Night to Benefit Raising Malawi at the United Nations in New York City.
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Barrymore poses during HBO’s 2009 Winter Television Critics Association press tour held at the Universal Hilton Hotel in Universal City, California.
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Barrymore and “Grey Gardens” co-star Jessica Lange arrive at the 66th annual Golden Globe Awards in Beverly Hills.
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Barrymore attends the premiere of “Grey Gardens” at the Ziegfeld Theater in New York City.
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The actress arrives at the 67th annual Golden Globe Awards, held at the Beverly Hilton Hotel in Beverly Hills.
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The star wears a blue gown at the Screen Actors Guild Awards in Los Angeles.
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Barrymore wears an orange Jil Sander dress at Covergirl’s 50th anniversary celebration in West Hollywood.
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Barrymore arrives for the “Big Miracle” premiere at AMC Loews Georgetown 14 in Washington, D.C.
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Barrymore attends a celebration of Elizabeth Taylor’s collection of Bvlgari jewelry at Bvlgari Beverly Hills.
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Barrymore attends the 40th annual People’s Choice Awards at Nokia Theatre L.A. Live in Los Angeles.
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Barrymore attends the “Miss You Already” premiere during the 2015 Toronto International Film Festival at Roy Thomson Hall in Toronto, Canada.
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Barrymore attends the European premiere of “Miss You Already” at Vue West End in London.
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Barrymore attends the Pokemon Afternoon Soiree at the Sunset Tower Hotel in West Hollywood.
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The actress attends the 74th annual Golden Globe Awards at the Beverly Hilton Hotel in Beverly Hills.
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Barrymore attends the premiere of “Santa Clarita Diet” at ArcLight Cinemas in Hollywood.
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Barrymore attends a conversation with Vanity Fair’s Mike Hogan at Kaufman Concert Hall in New York City.
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Barrymore attends the Beautycon Festival LA 2018 at the Los Angeles Convention Center in Los Angeles.
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Barrymore attends the 2018 Museum of Modern Art Film Benefit: A Tribute To Martin Scorsese at MoMA in New York City.
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