Relive the Most Unforgettable Hairstyles of the Last 20 Years

Kesha
Photo: startraksphoto.com

It’s no secret: In celebration of InStyle’s 20th anniversary, we’ve become slightly obsessed with all things nostalgic. We’ve relived everything from the most talked about dresses to the most gorgeous red lips of the last two decades—we even broke down the ’90s fashion and beauty trends that made a comeback (jelly sandals anyone?)

For our latest trip down memory lane, however, we’re combing through the most jaw-dropping hairstyles of the last 20 years, starting with Winona Ryder’s trailblazing crop in 1994. Of course, Jennifer Aniston’s “The Rachel” (aka the most requested haircut of all time), and Demi Moore’s extreme makeover for G.I. Jane were equally throwback-worthy. Curious to see who else made the cut?

PHOTOS: See the Most Unforgettable Hairstyles of the Last 20 Years
For more, pick up the October issue of InStyle, available on newsstands and for digital download now.

01 of 21

'94

Winona Ryder
Ron Galella, Ltd./WireImage

We may never revisit flannel button-fronts and chunky heels in quite the same way, but Winona Ryder’s spiky crop is a '90s hit that's still on replay.

02 of 21

'95

Jennifer Aniston
NBC Television/Getty Images

Cheek-grazing layers, pronounced volume, piecey ends...No matter how you break down the Rachel on Jennifer Aniston, we still can't explain its insane ascendancy on salon menus from L.A. to Buffalo.

03 of 21

'96

Demi Moore
Kevin Mazur Archive/WireImage

Talk about commitment to the craft. Demi Moore bared her biceps and her scalp for her role in the 1997 flick G.I. Jane. Respect.

04 of 21

'97

Gwenyth Paltrow and Brad Pitt
LIFE Picture Collection/Getty Images)

Before big-name mash-ups (Bryneth? Gwad?), the It couple of Gwyneth Paltrow and Brad Pitt branded a shared look of sleek, side-parted crops.

05 of 21

'98

Britney Spears
Youtube

Britney Spears worked not-so-innocent takes on schoolhouse uniforms, pigtails, and baby Ts, prompting girls the world over to braid it one more time.

06 of 21

'99

Lil Kim
Getty Images

OK, we admit that Lil Kim's lavender hair was the second thing we noticed when she hit the red carpet for the MTV Video Music Awards. (Need we address the pasty in the room?)

07 of 21

'00

Gisele Bundchen
Fernanda Calfat/WireImage

There was a time when beach waves happened naturally at the shore. Then Brazilian model Gisele Bündchen brought her loose bedhead locks to the runway. Dozens of salted styling sprays are bottled, and a hair icon is born.

08 of 21

'01

Christina Aguilera
Ron Galella, Ltd./WireImage

The genie escaped the bottle and made a bold statement with braids, pastel streaks, and a mini pompadour—trends Christina Aguilera still nails today (just maybe not all at the same time).

09 of 21

'02

SJP
Jim Spellman/WireImage

Even more memorable than when Jack Berger broke up with her on a Post-it? The moment Carrie Bradshaw (Sarah Jessica Parker) debuted her subtle layered bob during season 4 of Sex and the City. We had to wonder, How would it look on us?

10 of 21

'03

Jessica Simpson
ImageCollect.com

Call it ombré 1.0: versions of light blond hair with darker tips, spotted in the early 2000s on stars like Jessica Simpson and Christina Aguilera. What the look lacked in subtlety it could make up for in the maintenance department, buying copycats precious weeks between color appointments.

11 of 21

'04

Lindsay Lohan
Paramount/Courtesy Everett Coll

Lindsay Lohan’s Mean Girls makeover from home-schooled innocent to totally fetch Plastic is a constant reminder of why we're totally Team Lindsay.

12 of 21

'05

Nicole Richie
Jeff Vespa Archive/WireImage

Just how did Nicole Richie spin herself into an author, designer, and brilliant fashion star? She shed her famous sidekick and long layers in favor of a stylist (hello, Rachel Zoe) and a chic, smart bob.

13 of 21

'06

Rachel McAdams
L. Cohen/WireImage

Pastel hair isn't just for pop stars. Gwen Stefani and Pink may have sported candy-colored streaks, but Rachel McAdams gave them serious red-carpet cred, even styling them to hit up the SAG Awards the following year.

14 of 21

'07

Rihanna
Getty Images (3)

Good girl going, going... gone rad. Rihanna is known for her ever-changing locks-now. The strand-formations started gaining heat in 2007 and culminated a year later in an asymmetrical pixie with long peekaboo bangs courtesy of stylist Ursula Stephen in 2008.

15 of 21

'08

Katie Holmes
Steve Granitz/WireImage

So long, Joey Potter! Katie Holmes snipped neck-grazing strands in 2007, but the second she showcased a newly sharpened bob with blunt fringe in January, we knew she was a lock star to watch.

16 of 21

'09

Lady gaga
Dimitrios Kambouris/Getty Images

As Lady Gaga's supersize hair bow made repeat appearances, it became the beauty gift that kept on giving. Today it's in several GIFs we can't stop watching.

17 of 21

'10

Willow Smith
Jun Sato/WireImage

Not even whiplash could keep us from rocking out to Willow Smith mane anthem, "Whip My Hair," which we may or may not have sustained while watching the video on a loop.

18 of 21

'11

Justin Bieber
Kevin Winter/NBCUniversal

YouTube phenom Justin Bieber hacked off his signature swoop and swiftly lost thousands of Twitter followers. Who would have beliebed it?

19 of 21

'12

Viola Davis
Steve Granitz/WireImage

Meryl Streep may have won the Oscar, but Viola Davis’s auburn hair, worn in its natural texture, racked up all our votes.

20 of 21

'13

Beyonce
Instagram/Beyonce

Revealing a dramatic crop on Instagram? We wouldn't expect anything less from Beyonce, the woman who dropped an entire album on iTunes without a tweet's notice. #flawless.

21 of 21

'14

Kesha
startraksphoto.com

Call it the trend that just won't dye. Stars like Kesha, Katy Perry, and Nicole Richie are going purple. No, green. No, wait, blue... for now.

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