Drew Barrymore at the premiere of the film ‘The Freshman’ in 1990 wearing a red polka dot crop tee and washed out jeans.
The young actress at a 1990 screening of ‘Longtime Companion’ in Los Angeles wearing a white t-shirt paired with a leather motorcycle jacket and high-waisted jean shorts.
In 1991, the actress wore a cropped ivory sweater and ripped washed out blue jeans to Mann's Bruin Theater in Westwood, California.
In 1992, Barrymore attended the premiere of ‘Reservoir Dogs’ in Los Angeles wearing denim shorts.
Barrymore put a playful spin on classic tailoring in New York City in 1992.
Barrymore channeled classic Hollywood glamour with a hint of edge in a silver slip dress in 1993.
In 1995, the actress dressed like a tomboy in a striped sweater for the premiere of 'Tom Boy'.
At a movie premiere in 1996, Barrymore wore blue-tinted sunglasses with an oversized blue jean jacket and a Mickey Mouse bag.
Barrymore wore a '70s-inspired blouse to the premiere of “Charlie’s Angels” in Los Angeles in 2000.
In 2005, Barrymore wore a bright orange dress to the Covergirl Cosmetics’ 50th anniversary party.
Barrymore was a modern-day flapper at the 2009 HBO after party for ‘Grey Gardens’ in New York City.
In 2010, Barrymore wore a dazzling navy blue gown to the 16th Annual Screen Actors Guild Awards in Los Angeles.
Barrymore attended the 67th Annual Golden Globe Awards after party in 2015 wearing a Versace crystal-encrusted champagne gown.
Drew Barrymore attended Coach's 75th Anniversary fashion show in 2016 wearing a head-to-toe ensemble from the brand.
In 2017, Barrymore looked California cool while arriving in Paris.