Style Timeline: Drew Barrymore From Florals And Mary Janes To Fashion Icon

Kerry Pieri
Style Timeline: Drew Barrymore From Florals And Mary Janes To Fashion Icon
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Drew Barrymore is unique even within the realm of the outliers that comprise Hollywood. Heir to a veritable film dynasty, this 36 year-old may now be a beauty model, director, producer and actress, but she didn’t achieve it all without more twists and turns than the Pacific Coast Highway.

With a mom who could swap notes with the likes of Brooke Shield’s mother and Joe Jackson, Drew spent her tween years hanging out at industry parties and Studio 54 until taking an inevitable stint in rehab before she was old enough to take high school entrance exams. In case it’s news, the Cali-native also starred in one of the most famous sci-fi films of all time, E.T. The Extra Terrestrial, at the insane age of five.

Psychologists should probably study the resilient A-lister, but if you want more info you can always pick up her memoir, Little Girl Lost, published when she was just 14 (pre-Poison Ivy). We relish a good factoid, but what we’re really interested in are her fashion transitions from baby doll dresses and ringlets to ’90s poster child and the cool boho glam chick of today. Take a trip down Drew Barrymore Lane with us in the slideshow above.

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In an 'E.T.' press image, Drew is all floral dresses, mary janes and adorableness.

Jump ahead to 1992, a year after her autobio is published Drew changed up her image with the racy drama, 'Poison Ivy.' She had the look to match, with slicked back hair, dark lipstick and tighter than tight black dress.

In the flash-David-Letterman-and -compete-with-Winona-Ryder-for-It-girl-status year of 1993, Drew opted for lots of white (two layered slips to be exact) and an on-trend (you know, for 1993) choker accessory.

Drew fell off for a bit after 'Mad Love' co-starring Chris O'Donnell. She came back in the late 90s at the age of 23 with a form fitting embellished maroon strapless -       Atelier Versace number at a film premiere. It's not horrible, but it's maybe a touch prom.

In December of 2002, Drew took the office girl look a touch too far at the 'Confessions of a Dangerous Mind' premiere. Someone might have asked her to fetch a latte from Starbucks with those slingbacks.

In 2002 at the 20th Anniversary of 'E.T.' this Little Girl Lost must have felt decidedly found in a preppy/cas layered outfit featuring white pants and a military inspired jacket – signature dark lip intact.

All curly locks in 2004, lady got the sophisticated secretary thing down at the '50 First Dates' premiere in Germany.

Skip ahead to 2005, where Ms. Barrymore arrived at the 77th Annual Academy Awards at the age of 29 in a simple black strapless gown. A bit of a yawn, sure, but not god awful.

Was it the illustrious Paula Abdul who said, "take two steps forward, take two steps back?" This ill-fitting brown creation for a screening of 'The Perfect Catch' scares me and upsets Drew's style progression.

All minimalist sophisticate, this black ensemble count as a step forward for sure. The thespian was attending Francisco Costa's Spring 2007 Calvin Klein Collection wearing the designer.

Pretty in pink fits for the
64th Annual Golden Globe awards in 2007. I prefer a bit more edge but this Christian Dior is lovely nonetheless.

There's that edge I was griping about. Drew attended the Tribeca Film Institute's benefit screening of 'Everybody's Fine' in December 2009 in a sequined mini Emilio Pucci that looks young and fun and fresh on the 34 year old.

This is what we might call Drew's blue moment. For the 66th Annual Golden Globe Awards this Dior by John Galliano dress is all retro hotness and that hair isn't hurting a thing.

Just a few months later to celebrate her incredible performance in 'Grey Gardens' Barrymore wore a white Andrew Gn gown and Fred Leighton jewels and looked like an awesome Palm Beach in  the 60s lady with Bridget Bardot hair. Dying for it.

In a return back to the here and now, for a 2009 screen of 'Whip It', which she directed, Drew was all high fashion in Alexander McQueen. That two-tone hair might look wrong on anyone else, but the girl hasn't lost touch with her inner wild child.

A lovely red carpet look, Drew is a navy dream at the 16th Annual Screen Actors Guild Awards in pretty and poised Monique Lhuillier.

And just last week, proving she speaks fashion quite fluently now, this perpetual girl of the moment did 'The Late Show with David Letterman' in a Richard Chai blouse, Camilla and Marc pants and YSL Trib Two’s. Take notes studious style junkies.

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