From ’90s Icon to Modern Icon: Jennifer Aniston’s Ever-Evolving Beauty

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.

From her famous “Rachel” haircut to her signature blowout, we take look at Jennifer Aniston’s beauty evolution throughout the years.


Jennifer Aniston close-up with a flawless skin and dark hair in '87

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.


Jennifer Aniston with straight brown hair and a fresh face in '90

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.


Jennifer Aniston thick brown shoulder-length hair and deep red lipstick

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


Jennifer Aniston with wavy layered dirty blonde hair in '94

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.


Jennifer Aniston with the original "Rachel" haircut in '95

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


Jennifer Aniston smudged eyeliner and sleek updo with face-framing highlights

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.


Jennifer Aniston dirty blonde tousled beachy hair in '99

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.


Jennifer Aniston wavy dirty blonde bob with pink lipstick

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


Jennifer Aniston sleek blunt bob and pink monochromatic makeup

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


Jennifer Aniston long, wavy, dirty blonde hair and peach lip gloss

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


Jennifer Aniston long, straight, honey-blonde hair and pink lip gloss

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


Jennifer Aniston long bronde hair in loose waves and light pink makeup

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


Jennifer Aniston with a glowing complexion and long tousled waves

“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.”


Jennifer Aniston with center-parted stick-straight long hair

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


Jennifer Aniston ponytail with face-framing tendrils and "no makeup" makeup

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


Jennifer Aniston with dirty blonde hair and a hairline braid

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


Jennifer Aniston with a deep side part and dirty blonde hair with long layers

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.


Jennifer Aniston with long side-swept bangs and honey blonde hair

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.


Jennifer Aniston side-parted tousled beach waves with bobby pin

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


Jennifer Aniston sleek updo and a glowing complexion

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.


Jennifer Aniston with an angled hairline lob, shimmery eye makeup, and lip gloss

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.”


Jennifer Aniston long, straight, layered honey blonde hair

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.


Jennifer Aniston straight, dirty-blonde, side-parted hair

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.


Jennifer Aniston long, full dirty-blonde hair with a side flip

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.


Jennifer Aniston straight brunette lob

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.


Jennifer Aniston long, straight dirty blonde hair with deep side part

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.


Jennifer Aniston dirty-blonde hair with light pink lipstick at the SAG Awards

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


Jennifer Aniston wearing a ponytail with pulled-out strands in 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.


Jennifer Aniston dirty blonde blowout with peach lip gloss in 2017

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


Jennifer Aniston dirty blonde loose waves in 2018

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


Jennifer Aniston with wavy dirty blonde hair and bronzed skin

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


Jennifer Aniston with long, layered dirty blonde hair and minimal makeup

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.


Jennifer Aniston with straight, layered, dirty blonde hair and "no makeup" makeup

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.


Jennifer Aniston with long, straight, dirty blonde hair and minimal makeup

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.


Jennifer Aniston Proves She's Aging Like Fine Wine In A Black Bottega  Veneta Dress With A High Slit On 'The Tonight Show' - SHEfinds

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