Beauty Evolution: Drew Barrymore

Sweet Child O' Mine

By Abby Gardner

Look at that sweet face with just a touch of lip gloss. Note that even back in 1982, Drew had a thing for flowers in her hair. Keep reading to see how she wears them as a grown-up.

Dolled Up

I would have killed to play this kind of dress up in 1983. Drew's simple little updo with ribbons is perfect for any little girl. Also, I just got a strong urge to put Irreconcilable Differences in my Netflix queue. If you haven't seen it, I highly recommend it. Little Drew is great.

Trick Or Treat

Even super famous kids need to dress up for Halloween. And Drew is a great purple crayon. In foreshadowing of things to come many years later, she also rocks a glittery painted face.

Just Like Us

I may not have attended the Academy Awards with one of the Coreys back in 1989, but I most certainly showed up every day of middle school with that half-up poof in my hair.

Here Comes Trouble

That vampy lipstick just screams troublemaker, but in the prettiest possible way. It must also be noted that teens across America would have given just about anything to be hanging out with Drew and Balthazar Getty in 1990.

Go To The Light

This marks one of the first major color changes for the actress — to a California girl bleach blonde. This was the look she sported a few months later when her memoir, Little Girl Lost came out. It was the must-read for me and all of my friends in 1991.

Chop, Chop

Drew has never been afraid of the scissors, and we still never know when she's going to cut all her hair off again.

ON WONDERWALL: Drew's Fashion Looks Through The Years

Dark & Stormy

Remember 2000 Malibu Road, the short-lived television show starring Drew, Jennifer Beals and then-heartthrob Brian Bloom. Anyway, this was Drew's look from the show where she played a struggling actress. Lord, does this make me happy that the early '90s are over.

Ringlet Master

Drew chose Shirley Temple curls for the 1993 Billboard Music Awards. By the way, that dark matte lipstick shade was everything that year.

Good Girl Gone Bad

Not that she hadn't been a wild child in previous years, but Drew shocked fans by appearing on the cover of Playboy. Whatever you think about that, you can't argue with the fact that her smoky eye is super sexy and wearable.

Indie Rock

Even while having a grunge moment, Drew knows how to pick a cute accessory — this time a sweet little yellow barrette.

ON WONDERWALL: See More Pics of Drew

Flower Girl

Here come the daisies in what became Drew's signature look for a spell. They are a perfect counterpoint to her dark dress at the 12th Annual Video Music Awards in 1995.

Pin-Up Girl

There's something very old Hollywood-meets-flower-child in Drew's hair and makeup choices for the Oscars in 1998. This seems very appropriate for the girl who literally is old Hollywood and a hippie chick.

Color Guard

My favorite thing about this look is Drew's use of shimmery green shadow on her lids. It just goes to show that there's no reason color on your lids can't look great.

Pretty Baby

This is one of Drew's top five prettiest moments in my opinion. The warm tone of her hair is gorgeous, her brows are a wee bit thick and her skin is flawless. And don't even get me started on that major necklace.

Play Time

There are so many fun, quirky things going on in this shot from 2001. That blunt bob is so cute; the flower is back; and the yellow and blue eye shadow is perfectly playful.

Things That Make You Go Hmmm

Really, there's no telling what was going through Drew's mind as she was getting ready for the London premiere of Charlie's Angels: Full Throttle in 2003. Was she having a Geisha moment? Was she inspired by a street mime? We do give the lady credit taking big risks and doing as she pleases.

Shooting Star

I daresay that Drew is the only actress in Hollywood above the age of 10 that can actually pull off painting a star on her cheek. It's totally charming.

Ray Of Light

Obviously Drew likes yellow. And while I'm not sure this is a look you want to try for the office, I have to say it doesn't look completely terrible on her.

Such Great Heights

Drew was rocking the big hair trend all the way back in 2004 at the premiere of 50 First Dates. We're now seeing it on red carpets left and right.

The Sleekness

Drew can do straight and slick just as well as big and messy when it comes to her hair. And her makeup is simply stunning — apropos since she was announcing her CoverGirl beauty campaign.

A Tangled Web

Just when you think you've got her style figured out, Drew changes things up and goes back to her wilder roots — complete with a genius feather hair accessory.

Just The Tips

You gotta love edgy Drew with her blonde hair, dark black tips, blue nails and fingerless gloves. She's not afraid to live it up in her 30s and I think that's fantastic.

Retro Rewind

Drew completely captures everything that was chic about the 1920s with this look, but somehow doesn't look like she's wearing a costume.

Heads Or Tails

This might just be the perfect dressy ponytail. And Drew's amazing lashes and winged eye look fabulous, too. It's all very Catherine Deneuve.

Paint By Numbers

Face paint, part two. It seems Drew is still much like her younger self, loving to play dress up. Here she is at Bonnaroo loving life with a glittery face and a feather in her hair.

What A Tease

Not everyone was of fan of Drew's messy 'do at the 2009 Golden Globes, but it worked for me as she was there for playing one of the nuttiest characters ever, Little Edie Beale.

Bohemian Rhapsody

At the core of almost all of Drew's looks is the happy hippie spirit that she exudes. But she always puts her own twist on it. And that's why we love her so.