See Angelina Jolie’s Beauty Evolution, From ’90s Rebel to Red Carpet Royalty, in 26 Looks

She’s pulled off goth queen, Hollywood glamour—and everything in between.

• Angelina Jolie’s beauty has evolved over the years, shifting from rebellious ’90s to timeless Hollywood elegance.
• Throughout the decades, her ever-changing yet consistently striking looks have continued to inspire.

Actress, mom, and humanitarian Angelina Jolie does it all. And whether she’s dressed to the nines on the red carpet, taking a leisurely stroll in L.A., or tearing up the dance floor at her daughter’s college, the Hollywood veteran is a sight to be seen. As the daughter of Jon Voight and Marcheline Bertrand, Jolie was destined for greatness. Winning an Oscar at just 24, the Lara Croft: Tomb Raider star has moved the public with her on-screen charisma—and, of course, her jaw-dropping beauty.

Jolie, who recently turned 50, has famously opened up about her mental health struggles as well as the joys of parenting—proving that she is just as beautiful on the inside as she is on the outside. Observant fans may recall that the Academy Award-winning actress took a Hollywood hiatus, which lasted roughly from 2019 to 2024. But the Maria star is back, even stealing the spotlight at the 2025 Cannes Film Festival.

Keep scrolling to see Angelina Jolie’s 27 most memorable beauty moments from the past three decades.

As a student at Beverly Hills High School, where other notable alumni include Nicolas Cage and Carrie Fisher, Jolie already had a unique sense of style. “I wore black boots with big silver bat [charms] that dragged when I walked,” Jolie has said.

The year was 1998 (with blue eyeshadow and lined, glossed lips as proof) and the pixie-cropped actress won her first Golden Globe for TV biopic George Wallace; the following year she would receive a second statuette for her role in Gia.

Jolie went platinum for Girl, Interrupted, but limited her beauty routine to Carmex and lotion. That said, her ultra-light hair was a sharp pivot from her naturally dark tresses—and it made a bold statement.

In 2000, Jolie won an Academy Award for Girl, Interrupted, wearing Morticia Addams-like black extensions and winged eyeliner. A nude lip keeps the focus on her piercing blue eyes.

The Beyond Borders star, and new mother to adopted son Maddox, lightened up both her locks and makeup for a fresh look. Her pencil-thin brows were so early aughts—but they’re just as tantalizing in present day, as is wearing eyeliner on your waterline

The Alexander actress went for Old Hollywood glam with long retro curls and defined brows. Her caramel highlights add a nice touch of sun-kissed dimension.

The glamorous mom—who would expand her brood with daughter Zahara and become pregnant with Shiloh—sported a voluminous ’60s-inspired mane with her hair pushed back and liquid liner to the Mr. and Mrs. Smith premiere

For the Golden Globes, the A Mighty Heart star (and mom to the newly adopted Pax) donned a sleek bouffant updo that’s reminiscent of Old Hollywood. “Angelina loves wearing her hair away from her face,” hairstylist Ted Gibson has said.

“Her mouth is so large and beautiful,” makeup artist Janeen Schreyer has said of the born beauty. “I usually don’t color it.” Hairstylist Ted Gibson shows similar restraint: “She loves to keep a natural wave in her hair. It’s more sensual.”

Pregnant with twins Knox and Vivienne, the actress glowed in a high-volume style at the Kung Fu Panda premiere. As usual, her makeup was barely there—including shimmery shadow, black liner, and a light pink lip.

Nominated for her role in The Changeling, Jolie framed her face with an undone updo at the Screen Actors Guild Awards. Slightly volumized hair at the crown and matte pink lips are a nod to the ’60s.

For the Cannes Film Festival premiere of Brad Pitt’s Inglourious Basterds, Jolie played up her famous lips with a bright red color. Tousled, side-flipped hair keeps this beauty look from looking too overdone.

Loose, voluminous locks paired with soft cat-eye liner and glossy lips are the quintessential components of Jolie’s beauty look. Accessorizing with a smile adds to her allure.

Jolie looked characteristically stunning at the Golden Globes in 2011. Chestnut-colored hair perfectly complements her skin’s cool undertones, while her earrings and dress make her blue eyes appear more green.

For the Golden Globes, Jolie played up her incredible lips with a bright crimson hue. Her slicked-back updo is left a little loose, lending a softness to this otherwise bold beauty moment.

The actress attended the world premiere of her then-fiancé Brad Pitt’s movie World War Z just weeks after she revealed she underwent a preventative double mastectomy. She wowed the crowd in a black, floor-length Saint Laurent gown with her caramel locks in a casual curl.

Jolie brightens up her hair with an auburn hue that has an astounding amount of shine. To offer a nice contrast, the Original Sin co-star leaves her complexion and lips matte.

At the Critics’ Choice Awards, the star once again oozed Old Hollywood glamour in soft waves and a silver gown by Atelier Versace. Her full, lengthy lashes open up her eyes—which is most likely due to a trusty volumizing mascara.

Jolie wore her hair smooth and straight and opted for a pared-down beauty look for the Kung Fu Panda 3 Hollywood premiere at the TCL Chinese Theatre. The result is simple yet stunning, and ever so Jolie.

The actress opted for retro curls and a classic red lip in 2017, which popped even more given her fair complexion. A subtle smoky eye makes for an extra sultry finish.

Jolie enhanced her baby blues with graphic liner and softened her square-shaped face with face-framing tendrils. Paired with a semi-bouffant hairstyle, she gives off modern-day ’60s vibes.

The actress promoted her film Maleficent: Mistress of Evil with a slightly darker hair color and a classic red pout. Her dress, which has gold and silver sequins, is a masterclass in elegance.

At the UK Premiere of The Eternals, Jolie was glowing. Her radiant skin, minimal makeup, and glossy ash-brown hair prove that she is a timeless beauty.

From these gorgeous blonde curls, you’d never know that Jolie’s natural texture isn’t wavy. Combined with a red lip, her vibe is fun and fiery.

Considering bangs? Look to Jolie for inspiration. Her long, straight tresses get a subtle makeover with low-maintenance curtain bangs.

For her first appearance back at Cannes Film Festival in more than ten years, the A-lister kept it elegantly simple. Her glam had that no-makeup makeup feel with her blonde hair worn long and loose.