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The Celebrity Beauty Looks That Live Rent-Free in Cosmo Editors’ Minds

These unforgettable celeb hair and makeup moments shaped pop culture—and still inspire beauty trends today.

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Celebrities have always been the ultimate beauty blueprint. From the hairstyles and haircuts that we show our stylists, to dramatic Met Gala red carpets, celeb glam moments continuously shape how we think about beauty. The most iconic celebrity beauty moments aren’t just trends—they’re cultural resets and timestamps, identifying any given era with just one glam moment. Think of Taylor Swift’s continually sold-out lipstick shade and '90s supermodel blowouts that dominate mood boards decades later. These looks go viral, live rent-free in our minds, and become references years—hell, even decades—later.

So, team Cosmo did the seemingly impossible and pulled together the best celebrity beauty looks of all time. Whether you're in need of some hair or makeup inspiration or are just feeling nostalgic, enjoy these unforgettable glam moments.

1

Pamela Anderson's Updo

ccam awards
Patrick Riviere//Getty Images

"Pamela Anderson's updo and thin brows are forever etched into beauty history (and my brain). If it's a consistent Halloween costume decades later, you know it's good. "—JASMINE HYMAN, ASSISTANT BEAUTY EDITOR

2

Rihanna, CFDAs 2014

2014 cfda fashion awards arrivals
Gilbert Carrasquillo//Getty Images

"I think about this specfic Rihanna smokey eye all the time."—ANNABEL IWEGBUE, ASSOCIATE CULTURE EDITOR

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3

Zendaya, Challengers Premiere 2024

challengers tour hits los angeles
Eric Charbonneau//Getty Images

"Zendaya was absolutely glowing with this voluminous blonde bob and bow headband at the Challengers premiere in Los Angeles."—AI

4

Cher, Grammys 1974

cher at the grammys
Michael Ochs Archives//Getty Images

"The butterfly headpiece. The draping long hair. The purple eyeshadow and matching nails. The dramatic lashes. Need I say more?"—JH

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5

Marilyn Monroe's Red Lip and Blonde Bob

american actress marilyn monroe
Sunset Boulevard//Getty Images

"There’s no look that forever changed the beauty world quite like Marilyn Monroe’s signature glam. Her platinum bob, bold red lip, and iconic mole are the definition of Hollywood glamour, even more than half a century later." —JH

6

Doechii, Stephen Colbert Show 2024

three individuals seated on a staircase wearing similar outfits with plaid skirts and polo shirts
@doechii

"Doechii's trio of tied braids just happened to be at the same time as her rise to stardom. It perfectly signifies the kind of artist she is. Since this, her beauty looks have made it onto so many of our best-of lists (and even on the cover of Cosmo)."—BETH GILLETTE, BEAUTY EDITOR

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7

Jane Birkin's Bangs

jane birkin in 1970.
REPORTERS ASSOCIES//Getty Images

"No one does bangs better than Jane Birkin. The number of times I've seen this exact look on reference boards is proof. They're perfectly imperfect and the epitome of French girl chic." —LAUREN BALSAMO, BEAUTY DIRECTOR

8

Lady Gaga, 2019 Met Gala

the 2019 met gala celebrating camp: notes on fashion social ready
Theo Wargo//Getty Images

"Gaga's metallic lashes (and her four outfit changes) at the Camp Met Gala are unmatched."—SAM OLSON, ASSISTANT NEWS EDITOR

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9

Cindy Crawford's Iconic Blowout

17th annual cosmetic industry million dollary beauty ball & revlon's 60th anniversary celebration
Ron Galella, Ltd.//Getty Images

"The bouncy blowout defined the 90s, and no one did it better than Cindy Crawford. No wonder her classic supermodel hair is trending again 30+ years later." —LB

10

Diana Ross, 1975

mahogany
Michael Ochs Archives//Getty Images

"Diana Ross dominated the glam of the '70s with her unapologetically voluminous hair and bold, fluttery lashes. And she was the best dressed at the Met Gala 50 years later, might I add."—JH

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11

Audrey Hepburn, 1963

portrait of audrey hepburn
Hulton Archive//Getty Images

"I'd like to single-handedly credit the current rise of microbangs to Audrey Hepburn, aka the original it-girl."—JH

12

Tina Turner's Stage Hair

american singer tina turner
DENIZE alain//Getty Images

"Tina Turner's look was synonymous with her larger-than-life performance and presence. Her big hair is recognizable across generations—an accolade reserved for few." —LB

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13

Farrah Fawcett's '70s Blowout

farrah fawcett at golden globes
Fotos International//Getty Images

"When I go to the hair salon and want a bouncy blowout, Farrah Fawcetts waves are my exact inspo. I don't think she's ever had a bad hair day in her entire life. Volume goals."—JH

14

Kylie Jenner, 2014

2014 billboard music awards arrivals
Axelle/Bauer-Griffin//Getty Images

"This ombré teal hair moment made it onto every Tumblr moodboard and convinced myself and just about everyone in my senior class to dye their ends with Koolaid. It set Kylie's whole take on beauty apart from her smokey-eyed, glam sisters, complete with colorful hair and matte lips in a variety of shades."—BG

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15

Twiggy's Clumpy Eyelashes

twiggy in hollywood
Michael Ochs Archives//Getty Images

"Twiggy turned spidery mascara into an art form, stacking on layers of black until her lashes clumped just right. These signature, doll-like, exaggerated lashes were ultimate eye statement of the ‘60s."–JH

16

Jennifer Anniston's "The Rachel"

friends
NBC//Getty Images

"Jennifer Anniston's 'The Rachel' was the inspo behind my last haircut full of layers and dimension. Even more than 25 years later, it's the chic cut that everyone tries to mimic."—HANNAH OH, SHOPPING EDITOR

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17

Beyoncé, 2009

beyonce in concert los angeles, ca
Jason LaVeris//Getty Images

"My first core memory of Beyoncé was seeing these photos of her during her 2009 world tour. The wind-catching curls, bright pink lip, and glittery winged eye look are pure pop star perfection."—JH

18

Jenny Shimizu's Short Pixie

vivienne tam spring 1994 ready to wear runway show
WWD//Getty Images

"Jenny Shimizu completely redefined what a "supermodel" looked like in the early '90s. In a world of long, shiny hair, she embraced her androdynous looks (and, in turn, queerness) through her signature short cut that inspired lots of people (namely, lesbians and other LGBTQIA+ people) ever since. It led her to the runways and campaigns of some of the biggest fashion houses in the industry."—BG

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19

Amy Winehouse, 2007 MTV Europe Music Awards

amy whinehouse mtv music awards
Kevin Mazur//Getty Images

"Amy Winehouse was rarely spotted without her signature eyeliner. Her oversized cat eye is the blueprint for winged liner looks everywhere." —LB

20

Brooke Shield's Thick Eyebrows

"night of 100 stars ii" gala to benefit the actors fund after party
Ron Galella, Ltd.//Getty Images

"Even as thin brows trend, Brooke Shields’ fluffy arches from the '80s are still my ultimate inspiration. It’s me, my brow serum, and this inspo pic against the world."—JH

Headshot of Jasmine Hyman

Jasmine Hyman is the Assistant Beauty Editor at Cosmopolitan, where she writes about the latest beauty trends and must-have products. Her most prized beauty possessions are a meticulous skincare routine and salon blowouts. You’ll also likely find her in bed reading a good book or endlessly scrolling TikTok (spoiler: it’s usually the latter) while listening to Harry Styles’ entire discography on repeat. Follow her on Insta to be inundated with pictures of her meals. 

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