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The 25 Best Beauty Looks of the Last 25 Years

The 25 Best Beauty Looks of the Last 25 Years

By Angelique Serrano and Dianna Mazzone

Updated Aug 13, 2019 @ 9:00 am

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Like a fine wine, a truly great red-carpet beauty look somehow gets even better over time. So in celebration — and in honor of InStyle’s 25th birthday — we’ve rounded up 25 beauty looks that continue to stun years after their debut. (And because narrowing it down to just 25 was tough enough, the looks you’ll see here are presented in no particular order.)

And as you scroll through, don’t be surprised if inspiration strikes. Perhaps JLo’s 30-inch ponytail at the 2017 Met Gala will have you reconsidering extensions — or those bangs on Reese Witherspoon at the 2007 Golden Globes will inspire you to go all in during your next haircut. Or maybe you’ll feel compelled to swap your black eyeliner for striking white à la Kristen Stewart at the 2018 Cannes Film Festival.

So sit back, relax, and prepare for a virtual walk down memory lane. The most unforgettable red-carpet makeup and hair moments are right this way...

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1 of 25

Michelle Williams

Credit: Getty Images

2006 Oscars

To contrast with the actress’s sunny gown, makeup artist Kara Yoshimoto Bua selected a vibrant tomato red lipstick and let it pop against nearly bare skin.

2 of 25

Nicole Kidman

Credit: Russell Einhorn/Getty Images

1997 Oscars

With classic Hollywood glamour as inspiration, Kidman stepped out in vampy bordeaux lips and cleanly lined eyes. Hairstylist Enzo Angileri crafted a bun reminiscent of styles from the ’20s and ’30s. “Nothing is overdone,” he says.

3 of 25

Rihanna

Credit: Lars Niki/Getty Images

2014 CFDA Fashion Awards

With a nod to Josephine Baker, hairstylist Yusef topped the singer’s hair with a Swarovski-crystal head scarf that set her sultry eyes alight.

4 of 25

Julia Roberts

Credit: SGranitz/Getty Images

2001 Oscars

Perhaps even more memorable than Roberts’s Valentino Haute Couture gown? Her updo, carefully engineered with a signature dose of volume by legendary stylist Serge Normant.

5 of 25

Jennifer Lopez

Credit: Sean Zanni/Getty Images

2017 Met Gala

“I wanted to show off Jennifer’s face, so we pulled her hair back tightly,” says Chris Appleton, who created a dramatic ponytail with 30-inch extensions.

6 of 25

Kerry Washington

Credit: Taylor Hill/Getty Images

2018 Met Gala

Takisha Sturdivant-Drew wanted the actress to turn heads on the carpet: “I added some drama by giving the hair a lot of texture,” she says. Sewing a bold necklace into the wig (which Sturdivant-Drew had designed) was the final ornate touch.

7 of 25

Zoë Kravitz

Credit: Joe Scarnici/Getty Images

2018 Golden Globes

“We barely used any foundation,” says makeup artist Lisa Storey of Kravitz’s minimalist look. “The red lips with those green earrings were everything!”

8 of 25

Winona Ryder

Credit: Jim Smeal/Getty Images

1996 Oscars

The actress served up ’20s glam with rosy lips and finger waves that softened her iconic pixie cut.

9 of 25

Kate Hudson

Credit: SGranitz/Getty Images

2003 movie première

Echoing the hue of her retro dress, the monochromatic peachy pink tones on Hudson’s eyes and lips provided subtle luminosity. The pulled-back do added a sense of ease. “The look was sexy and chic without really trying,” says hairstylist David Babaii.

10 of 25

Lady Gaga

Credit: Jason Merritt/TERM/Getty Images

2016 Golden Globes

“Sophia Loren was certainly a reference,” says makeup artist Sarah Tanno, who created “wing-tipped eyes, strong brows, and nude lips” to go with the star’s platinum bob on her award-winning night.

11 of 25

Viola Davis

Credit: Ethan Miller/Getty Images

2012 Oscars

While green drop earrings played up Davis’s emerald smoky eyes, it was the actress’s hair that stole the show. “She stepped onto one of the biggest stages in the world in her natural hair — at a time when absolutely no one was wearing natural hair on the red carpet,” says hairstylist Jamika Wilson. “It was bold, courageous, and beautiful.”

12 of 25

Zendaya

Credit: Frazer Harrison/Getty Images

2015 Oscars

It all worked for the stylish star: the natural makeup, the gorgeous gown, and the long, powerful dreadlocks.

13 of 25

Rooney Mara

Credit: Jeff Kravitz/Getty Images

2012 Oscars

Red lips and graphic bangs make for one bold statement. “I cut her hair to demonstrate the beauty of her face,” says hairstylist Danilo. “Short, blunt fringe is such a confident beauty look.”

14 of 25

Uma Thurman

Credit: Mitchell Gerber/Getty Images

1995 Oscars

The pairing of a loose updo with neutral shadow and plummy lips stood out for all its subtlety. The effect was, quite simply, beautiful.

15 of 25

Reese Witherspoon

Credit: Frazer Harrison/Getty Images

2007 Golden Globes

This look is all about the bangs. Twelve years later, it still feels fresh. Hairstylist Mark Townsend says, “She showed the power of having the right fringe for your face shape.”

16 of 25

Cate Blanchett

Credit: Jeff Kravitz/Getty Images

2000 Oscars

When your accessory game is this eye-catching, pulled-back hair, radiant skin, and flushed lips are the best accompaniment.

17 of 25

Tracee Ellis Ross

Credit: Frazer Harrison/Getty Images

2018 Golden Globes

The actress took a memorable turn on the red carpet in a Marc Jacobs head wrap and showstopping scarlet lips.

18 of 25

Drew Barrymore

Credit: Steve.Granitz/Getty Images

1998 Oscars

The baby bangs, the skinny brows, the symmetrical, face-framing daisies: The actress remains ever the charmer.

19 of 25

Beyoncé

Credit: Dimitrios Kambouris/Getty Images

2015 Met Gala

“She started out with a topknot then pulled her hair down [into a ponytail] when she got out of the car,” says the singer’s makeup artist Sir John of the moments preceding her walk up the carpet. With a flawless complexion and glossy pink lips, “she’s never looked so young, fresh, and hot.”

20 of 25

Charlize Theron

Credit: Karwai Tang/Getty Images

2019 movie screening

A shiny brunet hue makes Theron’s berry lips and light eyes all the more striking.

21 of 25

Kristen Stewart

Credit: Beau Nelson

2018 Cannes Film Festival

Beau Nelson lined hereyes with miniature pearls to create this stunning look. “We’re always trying to do something new and adventurous,” he says.

22 of 25

Gigi Hadid

Credit: Isabel Infantes - PA Images/Getty Images

2017 makeup-launch party

“Gigi and I discussed fresh, simple, yet ultrafeminine makeup to complement her yellow dress,” says Maybelline New York global makeup artist Erin Parsons. “I basically applied blush and highlighter everywhere, including her eyes.” Hadid’s perfectly lived-in topknot completed the effortless vibe.

23 of 25

Lupita Nyong'o

Credit: Steve Granitz/Getty Images

2014 Oscars

“The Fred Leighton headpiece crowned her look perfectly,” says Nyong’o’s hairstylist Larry Sims. “Lupita felt like the queen that she is.”

24 of 25

Renée Zellweger

Credit: J. Vespa/Getty Images

2001 Oscars

Her cascading peekaboo waves and ruby lips are a throwback to Hollywood’s Golden Age.

25 of 25

Cameron Diaz

Credit: Kevin Winter/Getty Images

2003 Golden Globes

Fuchsia lips and pink-dabbed cheeks never looked cooler than when Diaz paired them with tousled beach-blond layers and a chic Chanel Haute Couture minidress.

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By Angelique Serrano and Dianna Mazzone

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The 25 Best Beauty Looks of the Last 25 Years

1 of 25

Michelle Williams

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Nicole Kidman

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Rihanna

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Julia Roberts

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Jennifer Lopez

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Kerry Washington

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Zoë Kravitz

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Winona Ryder

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Kate Hudson

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Lady Gaga

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Viola Davis

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Zendaya

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Rooney Mara

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Uma Thurman

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Reese Witherspoon

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Cate Blanchett

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Tracee Ellis Ross

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Drew Barrymore

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Beyoncé

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Charlize Theron

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Kristen Stewart

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Gigi Hadid

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Lupita Nyong'o

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Renée Zellweger

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Cameron Diaz

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