Celebrity Transformations Jennifer Aniston's Beauty Evolution From the '90s to Today This girl next door also knows Hollywood glam. By Krista Carter Krista Carter Krista Carter is a writer and editor with nearly a decade of experience working in beauty and fashion. InStyle's editorial guidelines Updated on January 9, 2023 @ 09:17AM Pin Share Tweet Email Trending Videos Photo: Handout/Getty Images When it comes to beauty, we'll be the first to admit that we love celebs who aren't afraid to take risks. After all, there's an element of surprise and delight that transpires when an A-lister debuts a bold new look, whether that be a dramatic haircut(s) or a Mattel-approved fashion trend. However, there's also something to be said of the opposite: celebs who have a signature style that they wear like a second skin. They know what looks and feels good for them, and as a result, exude confidence. Perhaps no one exemplifies this more than Jennifer Aniston who has been reinventing girl-next-door beauty since the late '80s — and the truth is, we can't seem to get enough. Jennifer Aniston Knows What She Wants From her famous "Rachel" haircut to her signature blowout, we take look at Jennifer Aniston's beauty evolution throughout the years. 01 of 34 1987 Seth Poppel/Yearbook Library The natural brunette (and natural beauty) graduated from New York City's LaGuardia High School of Music and Art in the late '80s. Her less-is-more approach to beauty lends her much appeal. 02 of 34 1990 Paramount/Shooting Star Aniston landed roles in Molloy and Ferris Bueller as a young 20-something. With her long brown hair and fresh face, her style was classic girl next door. 03 of 34 1992 Ron Galella/WireImage For the Leprechaun premiere, the actress wore her mahogany locks in long layers and sported ultra-'90s brick lipstick. The 8 Best '90s Makeup Looks to Recreate 04 of 34 1994 John Paschal/Celebrity The wavy-haired star got her breakout role as Rachel Green on Friends. Her pencil-thin brows were super on-trend — and maybe still are. 05 of 34 1995 Kevin Mazur/WireImage The cut that launched a thousand layers! "This was the original Rachel, with layered shoulder-length hair," said hairstylist Chris McMillan. Chrissy Teigen Just Gave "The Rachel" Haircut a 2020 Upgrade 06 of 34 1997 Starstock/Photoshot/Everett Collection A newly-minted movie star with 'Til There Was You and Picture Perfect, Aniston brought the focus to her bright blue eyes with smudged liner and an understated updo. 07 of 34 1999 Ron Davis/Shooting Star The Office Space star tried wild-child beachy hair for the Emmy Awards. "Jen's adventurous side — she did this look once and never went there again," said makeup artist Robin Siegel. 08 of 34 2000 SGranitz/WireImage "The one and only time I cut her hair short," McMillan said of this wavy bob. "She wanted to do something different." Your Definitive Guide to Every Type of Bob Haircut 09 of 34 2001 SGranitz/WireImage For the People's Choice Awards, the Rock Star actress wore her sleek cut straight. Blunt ends add some weight to fine tresses. 10 of 34 2002 Gregg DeGuire/WireImage Classic Jen: sun-kissed long layers and sheer, rosy makeup. 11 of 34 2003 Jeffrey Mayer/WireImage A bronzed glow and honeyed highlights accentuated the Bruce Almighty star's sea-blue eyes. 12 of 34 2004 Jeff Kravitz/FilmMagic Aniston hit the Golden Globes with loose bronde waves set off by a deep part complete with side-swept bangs. The Bangs Everyone Had 10 Years Ago Are Back 13 of 34 2006 Jen Lowery/Startraks "There's such a freshness about her look," said makeup artist Angela Levin of The Break-Up star. "She likes clean, glowing skin with soft, neutral makeup." 14 of 34 2007 Jean Baptiste Lacroix/WireImage "Her dress had a '60s mod feel, so we did bone-straight hair to match," said hairstylist Richard Marin. 15 of 34 2009 Kevin Winter/Getty Images Aniston showed off her natural beauty with "no-makeup" makeup and her hair styled in a pony with face-framing tendrils. How to Master Natural Makeup Looks Like an MUA 16 of 34 2009 Dan MacMedan/WireImage Aniston starred in He's Just Not That Into You and set trends with her Oscars hairline braid. 17 of 34 2009 Jim Spellman/WireImage She wore her long, layered hair with a deep side part at a New York City event. It worked to perfectly complement her strong jawline and face shape. Your Guide to the Perfect Haircuts for Your Face Shape 18 of 34 2010 Kevin Winter/Getty Aniston set trends at the Golden Globes with her piecey waves and honey highlights. A peachy lip really worked with the warm undertones of her skin and hair. 19 of 34 2010 Jackson Lee/Splash News Aniston embodied California cool when she sported beachy waves anchored by a bobby pin. 20 of 34 2010 Tony Barson/WireImage The actress switched up her style for a Bounty Hunter premiere with an easy updo. To keep her style in check, surely she applied some glossy, slicked-back hair products. 21 of 34 2011 REUTERS/Susana Vera /Landov The Just Go With It star debuted a sleek new cut courtesy of Chris McMillan. "I call it a hairline bob that follows the jawline down," the stylist told Allure. "It's angled and inspired by Vidal Sassoon haircuts and Julie Christie from Shampoo." 22 of 34 2012 Lionel Hahn/AbacaUsa.com Long, honeyed strands are Aniston's go-to cut and color. To keep this look from feeling overly simplified (read: boring), have your stylist incorporate face-framing layers to give your hair movement, body, and above all, personality. 23 of 34 2013 Michael Buckner/Getty Images for PCA For the People's Choice Awards, the actress opted for a classic beauty look. "I like to call it 'California babysitter hair,"' said Aniston's hairstylist Chris McMillan. Her makeup artist Angela Levin used the star's edgy ensemble as a starting point for her silvery eye makeup. "The inspiration was 'bad girl in a pretty dress,'" she said. 24 of 34 2013 JOHN FARR/SCHNEIDER PRESS/SIPA Looking to instantly — albeit, temporarily — change up your look? Follow Aniston's lead and opt for a hair flip. The We're the Millers star swept her enviable locks to one side for the film's Berlin premiere. Here's How to Figure Out Where to Part Your Hair 25 of 34 2014 Jamie McCarthy/Getty Images for Living Proof The actress dyed her tresses darker and went for a very on-trend lob at the Living Proof Style Lab in Boston. To complete her beauty look, a little gloss and mascara go a long way. 26 of 34 2014 Tim P. Whitby/Getty Images Top and bottom liner, plus voluminous mascara bring the focus to Aniston's blue eyes. To bring out their color even more, go with a complementary eyeshadow. 27 of 34 2015 Getty Images North America The Cake star showed off her bouncy blowout at the SAG Awards. A light pink lip looked lovely. 28 of 34 2016 D Dipasupil/FilmMagic Aniston swept her hair back into a playful pony for an appearance at the Zoolander 2 premiere. Shimmery shadow brightens her eyes and gives them some pizazz. 6 Updos That Are Actually Easy to Do 29 of 34 2017 Marc Piasecki/Getty Images The Friends alum wore her famous highlighted locks in a beachy blowout, polishing off the look with peach lipgloss. The Jennifer Aniston Hairstyle You Should Try In 2023, Based on Your Zodiac Sign 30 of 34 2018 Handout/Getty Images Aniston's loose waves are the definition of effortless beauty. To get their tousled texture, apply a texturizing spray. 31 of 34 2019 Steve Granitz / WireImage From the beach to the red carpet, Aniston wowed us with her highlighted waves, mesmerizing eyes, and enviable glow. The Morning Beauty Ritual Jennifer Aniston Hasn't Skipped In Nearly a Decade 32 of 34 2020 Steve Granitz / WireImage At the 77th Annual Golden Globes, Aniston's style was simple, yet elegant. A splash of makeup and natural waves were the bread and butter of her visually effortless look. 33 of 34 2020 Steve Granitz / WireImage Aniston's beauty formula — sleek dirty blonde hair, shimmery shadow, lip gloss, and an award-winning smile — resulted in red carpet perfection at the 26th Annual SAG Awards. 34 of 34 2022 James Devaney / GC Images Aniston radiates while on set of The Morning Show in New York City. Pearlescent eyeshadow, a pink pout, and thick tresses make this news anchor — fictional or not — a boss.