Drew Barrymore's Best Street Style Through the Years [PHOTOS]
Drew Barrymore has made major strides in her personal style throughout her career.
On the footwear front, Barrymore’s style ranges from sleek to bohemian. The “Miss You Already” actress often wears platform boots, pointed-toe pumps and platform sandals by Jimmy Choo, Gucci and Larroude, most frequently on her talk show “The Drew Barrymore Show.” Off-duty, she can also be seen in Converse sneakers, Dr. Martens boots and Crocs slides. As for outfits, the 2000s saw a grungier side to the thespian. These days, Barrymore sticks to playful silhouettes fixed with colorful prints and textures. In honor of Barrymore’s striking style while out and about, FootwearNews is recounting the star’s best street-style moments over the years.
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Drew Barrymore’s Street Style Evolution
Drew Barrymore in a full denim look in 1992.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing a formal suiting moment on Oct. 29, 1992.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing platform sandal heels and a crushed velvet maxi dress in black with a floral shawl in 1997 at Elizabeth Taylor’s 65th birthday.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing a denim jacket and blue trousers at promotional event for her new movie, “Ever After” in 1998.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing brown sandal heels and a floral dress with a brown cardigan at the 1998 Nickelodeon Kids’ Choice Awards.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing baggy jeans, sneakers and a t-shirt in Los Angeles at a Pediatric AIDS charity on June 07, 1999.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing brown boots, sweats and a crushed velvet cardigan out in L.A. in 2000.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing black slacks and a denim jacket in 2001 at “The Late Show with David Letterman.”
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing slouchy suit and a vest (L) with Lucy Liu in 2001.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing cropped jeans and knee-high boots spotted in 2005.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing purple high-top Converse sneakers in 2009.
Drew Barrymore’s Street Style Evolution
Drew Barrymore in Vans slip-ons in 2009.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing black gladiator sandals, jeans and a flannel on the set of “Going The Distance” in 2009.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing slouchy brown boots and a band tee spotted at LAX in 2011.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing long dress and block-heeled boots spotted in 2012.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wears sandals and floral frock in 2017.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing neon multicolored sneakers at a flea market in L.A in 2018.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing athletic sneakers was seen leaving Ulta beauty in New York in 2018.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing platform sandals with wide-legged pants and a leather jacket in 2018.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing red platform sandals at the “Today Show” in New York in 2018.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing black suede boots is seen in Los Angeles in 2018.
Drew Barrymore’s Street Style Evolution
Drew Barrymore pictured arriving at the Bondi Iceberg for her Flower Beauty event in 2019, wearing a floral jumpsuit.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing brown platform block heels is seen on Jan. 11, 2024, in New York.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing platform sneakers is seen on her birthday on Feb. 22, 2024, in New York.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing bright purple platform boots is seen going to WWE WrestleMania 40 on April 06, 2024, in Philadelphia.
Drew Barrymore’s Street Style Evolution
Drew Barrymore wearing black and cream playform heels is seen on the set of “The Drew Barrymore Show” on May 14, 2024 in New York.
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