Souzan Michael
February 22, 2019 11:00 am

Drew Barrymore is a true Hollywood icon. The actress, producer, director, author, and Flower Beauty founder has been in the industry since 1980. She, of course, achieved fame through her role in 1982’s E.T., and went on to become one of the most famous child actors of all time.

Since then, Drew Barrymore has become one of the most beloved actresses in Hollywood, starring in over 50 movies, and we’ve loved watching her style transform along the way. From the distressed denim and leather jackets that were her staples in the ’90s both on the red carpet and off, to her flower child period, to the easygoing glam we love her for now, Barrymore’s beauty and style evolution has been a fun one to watch.

Now, in celebration of her 44th birthday on February 22nd, we’ve compiled a list of all of our favorite moments of Drew Barrymore’s beauty and style evolution.

May 1983

Betty Galella/WireImage

At only 8 years old, Drew Barrymore had already started exhibiting her full glam potential. Who among us wouldn’t wear this entire outfit like, tomorrow?

March 1986

Ron Galella, Ltd./WireImage

11-year-old Barrymore is rocking the ultimate ’80s outfit here: oversized plaid blazer (with shoulder pads, of course), calf-length skirt, and big, tousled hair.

June 1989

Ron Galella, Ltd./WireImage

Looking like a true teenage dream in effortless waves, a chic dress, and cowboy boots.

May 1990

Ron Galella, Ltd./WireImage

Long blonde hair, an oversized leather jacket, and a red lip would go on to become Barrymore’s signature look for many years—and we wouldn’t have it any other way.

March 1991

Ron Galella/WireImage

From the brown lipstick to the distressed denim, paired with a simple cardigan, this is peak ’90s Drew Barrymore.

October 1992

Ron Galella, Ltd./WireImage

We’re obsessed with this short hair, jean shorts, and blazer combo. The chunky platforms make this look so very Drew.

December 1993

Ron Galella, Ltd./WireImage

At the Fourth Annual (!) Billboard Music Awards, Barrymore pulled out all the stops in this stunning white gown, multi-layered pearl choker, and Old Hollywood curls.

June 1995

Jean-Paul Aussenard/WireImage

Pairing a pastel nightgown with dark lipstick and flower hair pins, this is when we started to see Barrymore really coming into her own style.

January 1996

Ron Galella, Ltd./WireImage

Still on the massive nightgown trend of the ’90s, but this time with a printed coat and dark bob.

March 1998

Ron Davis/Getty Images

Barrymore brought the flower pins back for the 1998 Oscars, pairing the hair accessory with a glamorous black gown, for one of our favorite looks of hers ever.

April 1999

Arnaldo Magnani/Getty Images

Barrymore went full flower-child chic on her way to a taping of The David Letterman Show.

December 2002

KMazur/WireImage

All of a sudden, Barrymore emerged as a full-on glamazon, sporting voluminous, caramel waves, and a sleeker style.

April 2004

Carlos Alvarez /Getty Images

We love when Barrymore experiments with different hairstyles, and this massive blowout is no exception. Paired with a sleek dress and heels, this is one of her most daring beauty looks.

March 2005

Jon Kopaloff/FilmMagic

Opting for a darker shade of brown hair, the actress resurrected her love of dark lipstick, but this time paired it with a sophisticated gown.

April 2007

Jon Kopaloff/FilmMagic

Debuting her lightened locks, Barrymore stepped out in a bright yellow gown and gold stilettos—a color combo we don’t often see on the actress.

February 2008

Michael Loccisano/FilmMagic)

Trying out the strawberry blonde shade we now know and love her for, Barrymore looked amazing in glam curls and a cute minidress.

December 2009

Jim Spellman/WireImage

A long-sleeved sequin dress paired with black tights is so 2009, and this blonde shaggy bob might be our favorite Barrymore haircut of all time.

January 2010

Gregg DeGuire/FilmMagic

We love the updo and bare neckline with this dramatic, structural Monique Lhuillier gown.

November 2013

Gregg DeGuire/WireImage

Back to strawberry blonde and sporting the flowy, boho style we’ve come to expect from Barrymore these days.

January 2014

Jeff Vespa/WireImage

Choosing Monique Lhuillier once again, a pregnant Drew Barrymore looked radiant in florals at the 2014 Golden Globes.

December 2015

Robin Marchant/Getty Images

Donning beautiful mermaid waves and a printed dress, this is peak Drew.

October 2016

John Lamparski/WireImage

The actress certainly loves her prints, and she pulls them off well, as exhibited at BeautyCon in 2016, where she went for an easy blowout to let her dress do all the talking.

January 2017

Neilson Barnard/NBCUniversal/NBCU Photo Bank via Getty Images

Who can forget this breathtaking Drew Barrymore moment? The actress looked stunning in a metallic, pleated, yes, you guessed it, Monique Lhuillier at the 2017 Golden Globes.

July 2018

Axelle/Bauer-Griffin/FilmMagic

Easy waves, a red lip, platform heels, and a flowy dress. Can you get more Drew Barrymore than that?

Advertisement