Jennifer Aniston’s Iconic Looks from the ’90s to Present Day

1987

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.

1990

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.

1992

For the Leprechaun premiere, the actress wore her mahogany locks in long layers and sported ultra-’90s brick lipstick.

1994

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.

1995

The cut that launched a thousand layers! “This was the original Rachel, with layered shoulder-length hair,” said hairstylist Chris McMillan.

1997

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.

1999

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.

2000

“The one and only time I cut her hair short,” McMillan said of this wavy bob. “She wanted to do something different.”

2001

For the People’s Choice Awards, the Rock Star actress wore her sleek cut straight. Blunt ends add some weight to fine tresses.

2002

Classic Jen: sun-kissed long layers and sheer, rosy makeup.

2003

A bronzed glow and honeyed highlights accentuated the Bruce Almighty star’s sea-blue eyes.

2004

Aniston hit the Golden Globes with loose bronde waves set off by a deep part complete with side-swept bangs.

2006

“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.”

2007

“Her dress had a ’60s mod feel, so we did bone-straight hair to match,” said hairstylist Richard Marin.

2009

Aniston showed off her natural beauty with “no-makeup” makeup and her hair styled in a pony with face-framing tendrils.

2009

Aniston starred in He’s Just Not That Into You and set trends with her Oscars hairline braid.

2009

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.

2010

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.

2010

Aniston embodied California cool when she sported beachy waves anchored by a bobby pin.

2010

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.

2011

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.”

2012

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.

2013

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.

2013

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.

2014

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.

2014

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.

2015

The Cake star showed off her bouncy blowout at the SAG Awards. A light pink lip looked lovely.

2016

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.

2017

The Friends alum wore her famous highlighted locks in a beachy blowout, polishing off the look with peach lipgloss.

2018

Aniston’s loose waves are the definition of effortless beauty. To get their tousled texture, apply a texturizing spray.

2019

From the beach to the red carpet, Aniston wowed us with her highlighted waves, mesmerizing eyes, and enviable glow.

2020

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.

2020

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.

2022

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.

2023