Drew Barrymore style: how to get her look

I’m crazy about Drew Barrymore style. I’ve had a long-time girl crush on Drew. And I mean a really long time.

Drew is four years younger than me. So while I was stumbling, bleary eyed through my twenties, she was too. I always loved her quirky take on grunge fashion back then. She epitomised the new indie scene, with her pixie haircut, t-shirts, mini skirts and boots. And of course her perennially mischievous grin.

Those days are a little blurry for me but I do remember getting dressed for the many festivals, a-la-Drew. Placky daisies in my hair, a hot pink tartan mini skirt, white bonds singlet and black 12-hole docs. I still love flowers in my hair!


I know it’s impossible to imagine that we actually thought we were fashionable in the 90s. Bloody fashion train wreck. wasn’t it! But we did the best we could.

Since then, we’ve watched Drew grow up (as we all have, thank god) and become a mum. And get on with stuff as you do when you’ve married into a ridiculously wealthy, high-profile family (her husband’s dad used to be CEO of Chanel).

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Weird picture of Drew – this was her twitter pic to announce new baby Frankie

Drew Barrymore to me, represents a kind of freedom in fashion. She gets it way wrong sometimes. And she’s always been a bit of a ‘quirky’ presence in Hollywood. In recent times her confidence seems to have grown and she carries off an interesting combo of boho, vintage and modern haute couture.

I love the three looks below, they are from a few years ago but very understated glam. And don’t you just go wild for the big hair and white boho dress? If I was super skinny, that’s the kinda getup I’d be rocking: 1960s bombshell.


And the ones below show her more casual vibe. Drew is really good at jeans and a tee. She wears boyfriend jeans a lot, usually with heels (love that look) and she does a hat and striped shirt well too.  I think she even looks good yawning.


Some hints to help you get Drew’s look:

  1. Get a pair of boyfriend jeans and wear with heels. The girls on They All Hate Us do this really well.
  2. Be the master of your nude lippie destiny. I know I ALWAYS say that you should wear lippie. But Drew does the whole nude lip and smoky eye thing really well.
  3. Find a pair of classic sunnies and wear them all the freaken time. Ray bans are a bit done to death but I still like them. If you can get away with aviators, go for it. That shape doesn’t suit me at all, I look like a bloodhound with big droopy jowls.
  4. Dress for your shape. Drew is a little curvier and bustier than some of the other Hollywood wenches with their size 0 stick bodies and sunken chests. She wears well-fitting or tailored clothes that show off her figure and give her a lovely shape. She will often wear a slightly loose, low cut top or tee that doesn’t have a lot of excess fabric (which can make bustier people look bulky), with something more tailored on the bottom.
  5. Be confident. Wear clothes you like and that make you happy and don’t care what other people think. Dress for yourself.

Are you a Drew fan? Which of her looks do you feel most comfortable in?


Written By

Gillian is a marketing savant and brand strategist with over 20 years of experience in above and below the line marketing, digital strategy and creative direction. She is an exceptional people person who loves to collaborate with clients every step of the way to achieve the best possible outcome. Gillian is also a successful makeup-artist and make-up obsessive who loves to share her tricks of the trade and help women to look good and feel great.

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