Some of the Edgiest (or Just Plain Weirdest) Celebrity Hairstyles

Natalie Dormer,

NATALIE DORMER

the sweet blonde from Game of Thrones, showed up at the SAG Awards in a gown that landed her on our Best Dressed List and a haircut that received gasps of shock.

Dormer's act of bravery got us thinking about all the women who caused a stir by chopping, dying, or simply styling their locks for an out-of-the-box moment. Some good, some bad, these are the ladies who've made us look twice over the years.

Helen Mirren, 2013

The Queen can do no wrong—even when she showed up at the EE British Academy Film Awards with a bubblegum pink pixie (Age: 67).

HELEN MIRREN

Angelina Jolie, 2000

Angelina Jolie usually goes for solid basics and a wavy blowout. But her craziest hair moment was when she won the Oscar for Girl, Interrupted. You may, however, have been too distracted by her uncomfortable smooch with her brother to notice that her black Morticia Addams locks reached down to her derrière.

ANGELINA JOLIE

Rihanna, 2011

Riri has had so many hair moments, it was hard to choose. But what stands out the most for us was when she went Crayola red—literally no auburn or strawberry hues here—accompanied by some major curls.

RIHANNA

Cassie, 2012

We credit Cassie with starting the whole half-shaved look, or at least with making people notice. Now that it has become such a trend, is it time to take it a step further and shave it all off? Probably not, but with a face like hers, she'd still certainly be stunning.

CASSIE

Drew Barrymore, 2009

DREW BARRYMORE

This moment may have gotten lost in your internal stockpile of Drew Barrymore images from over the years, but circa her directorial debut of the roller derby flick Whip It, the hair chameleon decided to dip it

Jada Pinkett Smith, 2013

We could have had any of Willow Smith's hairstyles on this list, but we decided to go straight to the source. If Jada Pinkett Smith's shaved, bleached sides are any proof, her daughter's affinity for experimental hairdos comes from her maternal side.

JADA PINKETT SMITH

January Jones, 2013

JANUARY JONES

Despite her conventional character on Mad Men, January Jones is no Betty Draper on the red carpet. She is never afraid of experimenting and has shown up with sparkling blue eye shadow and rose gold streaks in her hair. We particularly like the exaggerated pompadour with slicked-back sides she sported at last year's SAGs.

Jennifer Aniston, 1999

JENNIFER ANISTON

Two things we often don't hear together: Jennifer Aniston and fashion risk, and dreadlocks and chic. But back in the day on the Emmy red carpet, the originator of the not so edgy "Rachel" went for it and looked like the haute hippie we all wanted to be. 

Nicole Richie, 2013

NICOLE RICHIE

From boho chic to grandma chic, Nicole Richie is always ahead of the trends. For the Met Gala a gray updo got her in touch with her elderly side—and she looked gorgeous per usual. 

Gwen Stefani, 1998

GWEN STEFANI

Before her white blonde hair and red lip uniform (which seems oddly tame in comparison) was fully cemented, the now mother-of-three would experiment with just about anything beauty wise. For the MTV Music Awards? Blue buns and a bindi, please. 

Jennifer Morrison, 2013

JENNIFER MORRISON

Jennifer Morrison for the win! The actress's faux mohawk at the "PUNK: Chaos to Couture" Met Gala is one of the coolest (and event appropriate) hairstyles we've seen—and you can go back to normal the next day! 

Kelly Osbourne, 2014

KELLY OSBOURNE

So this may be a somewhat pop star, crazy color hair pick that we were going to avoid, but hear us out. Anyone who has stuck with a shade such as lavender for this long (she's had it since 2011!) deserves to be on our list. 

Alice Dellal, 2011

ALICE DELLAL

We love seeing a heiress/model/socialite with dark grown-out roots and part of her head shaved,  at the ELLE Style Awards she is the epitome of punk rock chic.