Fashion & Beauty / Vintage Style

Drew Barrymore: Fashion Moments on Film

A celebration of the best looks from Drew Barrymore's 90s cinematic heyday

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Drew Barrymore in Boys on the Side (1995)
Drew Barrymore in Boys on the Side (1995)

With her dungarees, fishnet tops and crucifix necklaces, Drew Barrymore was a paradigm for 90s grunge style. We grew up with her double stonewash denim, ever-changing hair, tie-dye T-shirts and battered biker jackets. We knotted our shirts just like Drew, and put flowers in our hair. Along with Winona Ryder, she was an actress who teenagers could really identify with. 

She was also the epitome of Hollywood adolescent rebel: she partied at Studio 54 at the tender age of 9, was in rehab by 14 and engaged by 16. She became the face of Guess in 1993, followed by a Miu Miu campaign in 1995. We have watched her mature from teen wild child to one of Hollywood’s most loved actresses. Following her 40th birthday this weekend, we take a look back at our favourite 90s Barrymore fashion moments on film.

Poison Ivy (1992)
Aged seventeen, with a whole host of life experience already under her belt, Barrymore played a reckless seductress in drama-thriller Poison Ivy. The film was a box office flop but a fashion triumph, as we fell for Barrymore’s wild blonde mane, trashy tops, torn denims and leather.  

Boys on the Side (1995)
This fashion road trip celebrates plenty of our favourite Drew-isms: denim overalls, beaded chokers, floral hair pieces and those springy short blonde tousles.

Scream (1996)
Who didn’t feel nervous alone in the house when the phone rang after watching this film? Drew’s blonde bob is now a 90s heirloom, along with her boyfriend jeans, ribbed-knit sweater and that chunky white cordless phone.

The Wedding Singer (1998)
This film pays tribute to the gloriously tacky 80s. Barrymore plays Julia, in loose-fit blouses, cardigan twinsets, denim jackets, polka dots and pearls. Special mention to co-star Adam Sandler’s bouffant mullet hairstyle.

Never Been Kissed (1999)
The white feathered cardigan on her first day at school, the pink lamé prom dress, the succession of sheer printed blouses. Never Been Kissed is a classic chick flick rom-com. Here’s to the class of ’99.

See Drew Barrymore in a stunning story shot by Inez & Vinoodh from AnOther Magazine S/S05.

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