1Pamela Anderson's Updo
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
2Rihanna, CFDAs 2014
Gilbert Carrasquillo//Getty Images"I think about this specfic Rihanna smokey eye all the time."—ANNABEL IWEGBUE, ASSOCIATE CULTURE EDITOR
Advertisement - Continue Reading Below
3Zendaya, Challengers Premiere 2024
Eric Charbonneau//Getty Images"Zendaya was absolutely glowing with this voluminous blonde bob and bow headband at the Challengers premiere in Los Angeles."—AI
4Cher, Grammys 1974
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
Advertisement - Continue Reading Below
5Marilyn Monroe's Red Lip and Blonde Bob
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
6Doechii, Stephen Colbert Show 2024
@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
Advertisement - Continue Reading Below
7Jane Birkin's Bangs
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
8Lady Gaga, 2019 Met Gala
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
Advertisement - Continue Reading Below
9Cindy Crawford's Iconic Blowout
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
10Diana Ross, 1975
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
Advertisement - Continue Reading Below
11Audrey Hepburn, 1963
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
12Tina Turner's Stage Hair
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
Advertisement - Continue Reading Below
13Farrah Fawcett's '70s Blowout
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
14Kylie Jenner, 2014
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
Advertisement - Continue Reading Below
15Twiggy's Clumpy Eyelashes
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
16Jennifer Anniston's "The Rachel"
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
Advertisement - Continue Reading Below
17Beyoncé, 2009
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
18Jenny Shimizu's Short Pixie
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
Advertisement - Continue Reading Below
19Amy Winehouse, 2007 MTV Europe 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
20Brooke Shield's Thick Eyebrows
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

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.
Advertisement - Continue Reading Below
Advertisement - Continue Reading Below
Advertisement - Continue Reading Below