The Beautiful Transformation of Angelina Jolie: A Journey from Child Actress to Acclaimed Award-Winner

She’s showcasing both goth queen beauty and glamorous red carpet looks, as well as everything in between.

Angelina Jolie with a mid-length blowout and red lips in 2017

Actress, mother, and humanitarian Angelina Jolie is a multi-talented individual who leaves us in awe with her impressive achievements. Whether she is dressed elegantly on the red carpet, taking a leisurely stroll in LA, or tearing up the dance floor at her daughter’s college, the Hollywood veteran never fails to impress. As the daughter of Jon Voight and Marcheline Bertrand, Jolie was destined for greatness. Winning an Oscar at just 24, she has moved us with her imposing talent and, of course, her stunning beauty. In this article, we highlight some of Angelina Jolie’s most memorable beauty moments from the past three decades. First up, we take a look at 1986.

11-year old Angelina Jolie with long hair and teased side bangs

When Jolie was just 11 years old, her beauty was already apparent in a photo where she was seen wearing pearls and lace, exuding Hollywood glamour. This image of her is layered with elegance and sophistication that truly showcases her natural beauty.

Angelina Jolie as a high school student in '91 with long, straight hair

As a student at Beverly Hills High School, Jolie already had a unique sense of style. She shared that she used to wear black boots with big silver bat charms that would drag when she walked. Despite being 31 years old now, Jolie admits that cool teen girls still intimidate her. This memory dates back to 1998.

Angelina Jolie with a sleek pixie, blue-gray shadow, and lip tint in '98

In 1998, a short-haired actress won her first Golden Globe for her role in the TV biopic George Wallace. The following year, she received a second statue for her performance in Gia. Today, she is known for her iconic pixie cut and has even inspired a list of 25 different cuts that can suit any face shape. Moving on to 1999…

Angelina Jolie with blonde shoulder-length hair

Jolie achieved a platinum blonde hair color for her role in the movie “Girl Interrupted,” but she limited her beauty routine to using only Carmex and lotion. If you’re looking to go platinum blonde without damaging your hair, here are some tips from 2000.

Angelina Jolie long black hair and winged liner

In 2003, she received an Academy Award for her performance in the movie “Girl”. During the awards ceremony, she interrupted the audience’s attention by wearing black extensions and winged eyeliner reminiscent of Morticia Addams. Her nude lip kept the focus on her eyes. This unique and daring fashion statement earned her well-deserved attention and praise.

Angelina Jolie with a high ponytail, pink blush, lip gloss, and eyeliner

The star of Beyond Borders and new mother to adopted son Maddox, brightened up both her locks and makeup for a fresh look. Her pencil-thin brows were so early 2000s – and present day.

Angelina Jolie voluminous curls and caramel highlights

The Alexander actress opted for a vintage Hollywood look with long retro curls and defined brows. Her caramel highlights add a nice touch of sun-kissed dimension. This was back in 2005.

Angelina Jolie long, voluminous hair and a nude lip

In 2007, the stylish mother-of-six, who was set to expand her brood with daughter Zahara and become pregnant with Shiloh, showed off a voluminous ’60s-inspired mane and liquid liner at the premiere of Mr. and Mrs. Smith. Stephen Shugerman/Getty Images captured the glamorous moment.

Angelina Jolie with a sleek bouffant updo, light pink lips, and liner

For the Golden Globes, Angelina Jolie, a famous actress and newly-adopted mother to Pax, sported a sleek updo. According to her hairstylist Ted Gibson, “Angelina loves wearing her hair away from her face.” Here are six easy updos that you can try. (Note: This content has been paraphrased to avoid plagiarism.)

Angelina Jolie loose, half-up, half down long hair

In 2008, makeup artist Janeeen Schreyer and hairstylist Ted Gibson both praised the natural beauty of an unnamed individual with a large and beautiful mouth. Schreyer noted that she usually avoids coloring the mouth, while Gibson commented on the individual’s preference for keeping a natural wave in their hair, which he described as sensual.

Angelina Jolie with long, thick brown hair with volume at the crown

At the Kung Fu Panda premiere, actress Everett Collection glowed in a high-volume style while pregnant with twins, Knox and Vivienne. If you have fine hair and want to achieve a thicker mane, consider investing in volumizing hair products. This content was originally published in 2009.

Angelina Jolie with a '60s-inspired updo and nude lip

Jolie, who received a nomination for her role in “The Changeling,” attended the Screen Actors Guild Awards with a slightly undone updo and matte pink lips, nodding to the 1960s. Her hair was volumized at the crown, giving her a relaxed yet elegant look.

Angelina Jolie with long, caramel-highlighted hair and red lipstick

At the premiere of Brad Pitt’s “Inglourious Basterds” at the Cannes Film Festival, Jolie sported bright red lips that added to her beauty. Her tousled, side-flipped hair complemented the overall look, but some critics thought it was a bit overdone. If you’re looking for the best red lipsticks, check out our tested and reviewed list of 13 options. That was back in 2010.

Angelina Jolie with loose, voluminous locks, soft cat-eye liner, and glossy lips

Steve Granitz/WireImage Angelina Jolie’s classic look in 2011 featured loose, voluminous locks complemented by a soft cat-eye liner and glossy lips.

Angelina Jolie with long, thick hair, a nude lip, and green sparkly gown

At the Golden Globes, Jolie was stunning as usual with her characteristic beauty. Her chestnut-colored hair perfectly complemented the cool undertones of her skin. If you’re a brunette looking for some new hair color ideas, check out these 11 suggestions. This content was originally published in 2012.

Angelina Jolie with an updo, red lips, and sultry eye makeup

During the Golden Globes, Jolie showcased her stunning lips with a bright crimson shade. Her slicked-back updo was left slightly loose, adding a softness to this otherwise bold beauty moment.

The movie premiere of “World War Z,” starring Brad Pitt, was attended by the actress who had recently undergone a preventive double mastectomy. She impressed the crowd with her black Saint Laurent gown and casual curls in caramel locks. This event took place just weeks after she made her surgery public.

Angelina Jolie with long auburn hair, a smoky eye, and nude lip

Jolie adds a touch of reddish-brown to her hair, while keeping her complexion and lips matte for a nice contrast.

Angelina Jolie with long sleek curls and voluminous lashes at the 20th Annual Critics' Choice Movie Awards

During the Critics’ Choice Awards, the celebrity exuded Old Hollywood glamour with soft waves and a silver gown by Atelier Versace. Her lengthy lashes beautifully opened up her eyes and made us reach for our favorite volumizing mascara.

Angelina Jolie with straight dark brown hair and eyeliner

Jolie opted for a sleek and straight hairstyle for the Hollywood premiere of Kung Fu Panda 3 held at the TCL Chinese Theatre. The result was a simple yet stunning look. This event took place in 2017.

Angelina Jolie with a blow-out, fair skin, and red lips

In 2017, the actress showcased a classic red lip and retro curls, with an added touch of allure through a subtle smoky eye.

Angelina Jolie with glossy lips, graphic liner, and a semi-bouffant

Jolie added some boldness to her baby blue outfit by incorporating a graphic liner. The semi-bouffant hairstyle she paired it with gives off modern-day ’60s vibes.

Angelina Jolie chic updo with graphic liner and red lipstick

The actress promoted her latest film, “Maleficent: Mistress of Evil,” with a slightly darker hair color and a classic red pout. This content was originally published with the photo credit to Samir Hussein/WireImage in 2021.

Angelina Jolie long, chocolate brown hair and full brows

During the UK premiere of “The Eternals,” Jolie’s beauty was truly timeless. Her radiant skin, minimal makeup, and glossy ash-brown hair all added to her glowing appearance. It was evident that she is a classic beauty.

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