20 of the Most Gorgeous Red Lips in the Last 20 Years (And How to Get the Look!)

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As Gwyneth Paltrow once wrote in her cookbook, My Father's Daughter, "Beauty, to me, is about being comfortable in your own skin. That, or a kick-ass red lipstick." Okay, so maybe a kick-ass red lipstick won't entirely transform your life, but can anything as quickly and as easily turn you into a glamazon?

For a very long time, the red lip has been a sign that a woman is daring and sensual—and a true class act. "Red lips go back to Snow White," the late makeup legend Kevyn Aucoin told InStyle. (He worked with Julianne Moore, Julia Roberts, and countless other superstars before his untimely death in 2002.) As if you need proof of just how enduring the red lip is, see the photos of above of Madonna in 1996, Adele in 2013, and Rihanna in 2009—all sporting a rose-colored pucker and all looking amazing no matter what the decade.

In honor of InStyle's 20th anniversary, we went back into our archives to find tried-and-true advice on pulling off the makeup mainstay, and to pay tribute to the female stars who have proved over the last 20 years that a red lip is as timeless as any beauty look can get.

Check it out now.

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—Jeryl Brunner

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1 of 21

2013 - Adele

Jon Kopaloff/FilmMagic

The matte red Adele typically wears (like at last year’s Grammys) makes a bold, velvety, yet subtle statement. And it looks amazing with the singer’s porcelain skin.

2 of 21

2002 - Reese Witherspoon

Ron Galella/WireImage

According to makeup artist Jo Strettell, who has worked with Witherspoon, “as a general rule, fair skin looks best with reds that have orange undertones, while darker skin is flattered by richer, more burgundy shades.”

3 of 21

2012 - Emma Stone

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Celebrity makeup artist, Toni G advises applying lipstick straight from the tube onto the center of the lips, then mushing lips together to send color out to the edges, helping to avoid harsh lines. Blot as needed.

4 of 21

2009 - Rihanna

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Olive skin tones can pull off warmer tomato reds like Rouge d'Armani lipstick No. 401. For Rihanna's shine, add a touch of gloss.

5 of 21

2009 - Scarlett Johansson

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“I'm a huge believer in the power of lipstick, especially red—it's like instant glamour in a tube,” Johansson told us back in 2009. “I don't remember the first time I wore it, but I was young, probably in my early teens.”

6 of 21

2012 - Angelina Jolie

Kevin Mazur/WireImage

At the 2012 Oscars, Jolie elevated her basic black dress up a million notches with her red-to-the-max crimson pout (compliments of MAC lipstick in Russian Red.) Her makeup artist Toni G suggests gently sloughing off dead skin with a damp cloth before applying lipstick to help smooth lips.

7 of 21

2011 - Zoe Saldana

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Zoe Saldana adds a bright lip to create a focal point on her face. For a long-lasting stain, the trick is to paint your lipstick with a fine-tip makeup brush and blot between coats.

8 of 21

2012 - Katy Perry

Jason Merritt/Getty Images

If you’re not feeling bold enough to wear red, celebrity makeup artist Jo Strettell suggests starting with a stain. “Then gradually add more red as you adjust to the color,” she advises. “Before you know it you won't be able to leave the house without it."

9 of 21

2006 - Kerry Washington

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A deep brick or burgundy shade is spectacular on darker complexions. We love Nars lipstick in Fire Down Below.

10 of 21

1996 - Madonna

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A longtime red devotee, Madonna even has her own official lip color. Gina Brooke, the superstar’s makeup artist, collaborated with Make Up For Ever to create Aqua Rouge #8 specifically for the star.

11 of 21

2009 - Nicole Kidman

Chris Jackson/Getty Images

How to get Nicole Kidman's perfectly blended red pout? Celebrity makeup artist Jo Strettell says that the best way to prevent color from bleeding is to outline lips with a liner that matches your lipstick. Soften the line by dragging it inward with a lip brush. Apply lipstick from the tube, using a lip brush to even out the color.

12 of 21

1997 - Liv Tyler

Fred Duval/FilmMagic

Blue-based cherry red lipsticks are flattering on fair-skinned women. Adding a bright red lip gloss can really help accentuate lips even more, shared Liv Tyler's makeup artist Pamela Geiger.

13 of 21

2013 - Jessica Chastain

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Jessica Chastain told us that she rocks bold red lips with “sassy and feminine” YSL Rouge Pur Couture The Mats Rouge Rock No. 203. "I just dab it on my lips and press them together, then use my finger to pat the color down even more so it looks like a stain,” says the actress. “I don't like the feel of thick lipstick—and I definitely don't like seeing it smeared on my teeth.”

14 of 21

2008 - Anne Hathaway

Lalo Yasky/WireImage

The Oscar winner says her go-to color is red because “it's powerful and energizing." It also looks great with her dark tresses, doe-shaped eyes, and alabaster skin.

15 of 21

2004 - Gwen Stefani

KMazur/WireImage

Some things never go out of style, like Stefani's pale, powdered face, arched eyebrows, and red lips. "The makeup goes on every day, even if I'm not going anywhere," she told us.

16 of 21

2000 - Julianne Moore

Justin GoffUK Press via Getty Images

"Red lipstick looks beautiful but also a little edgy," Julianne Moore's late makeup artist Kevyn Aucoin, told 'InStyle.' And with her fair skin and red tresses, Moore can look fabulous in a variety of shades, including a true tomato red.

17 of 21

1999 - Christina Aguilera

Jeff Kravitz/FilmMagic, Inc

“Whenever I'm in the studio, even if I'm wearing sweatpants, I have my red lipstick on,” Aguilera told 'InStyle.' Her signature red lips and bombshell tresses have remained her staple look.

18 of 21

2006 - Charlize Theron

John Shearer/WireImage for GLAAD

Makeup artist Shane Paish, who has worked with Theron for years, has been known to layer the actress’ lips with lip balm, then lightly line and fill in her mouth with lip pencil, finally painting a very sheer, precise layer of cream-based lipstick with a lip brush to maximize staying power.

19 of 21

2007 - Blake Lively

Brad Barket/Getty Images

To help the rich color stay put, fill in lips with a pencil before blending on lipstick with a lip brush. Prep lips with a balm to keep them moist.

20 of 21

2013 - Jessica Alba

Jason Merritt/Getty Images for Spike TV

Alba's olive complexion really glows with her signature dark red or even a warm tomato shade.

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