Angelina Jolie's Stunning Style Transformation

After three decades in the spotlight, Angelina Jolie is undeniably one of the most influential Hollywood stars of her generation. And while her impact on the film industry as well as her humanitarian work are to be admired, today, our sole focus is on her style. "Angelina Jolie is one of those rare stars whose style feels instantly recognizable. Her looks are always pared back, powerful and clearly highly considered," SilkFred head stylist Megan Watkins explained to Hello! in 2025.

It's clear that we can learn plenty of style secrets from Angelina Jolie, but just like every star in the spotlight, her looks have changed over the years. Teaching us how to embrace edgy and dark fashion? Jolie did that in the early 2000s. Becoming a true expert at method dressing? The actor nailed it in the late 2010s. Now, as she continues to surprise us with an occasional bold color or dramatic silhouette, let's take a closer look at just how her style got to where it is!

Even before she had her big breakthrough as an actor, Angelina Jolie was no stranger to the industry. As the daughter of actors Jon Voight and Marcheline Bertrand, Jolie spent quite a lot of her teenage years attending Hollywood events. Just before she started high school, Jolie's mother — who was separated from Voight by then — had moved Jolie and her brother to Los Angeles. While living there undeniably helped Jolie get some of her early '90s acting jobs, it also influenced the young star's style.

The punk-rock scene and its aesthetic played a major role in Jolie's early style, and while she dressed in classic '90s pieces for red-carpet events alongside her father, soon the star would begin exploring grungier looks in public, too.

The late '90s played a pivotal role in Angelina Jolie's style evolution. In 1996, the actor — who was in her early 20s — married actor Jonny Lee Miller, whom she had met on the set of the film "Hackers" a year prior. While she had acted in quite a few notable projects by then, it was her portrayal of model Gia Carangi in the 1998 film "Gia" that truly put Jolie on Hollywood's map. With the role, a drastic change in her look took place as Jolie cut her hair short.

The importance of the role for Jolie's style evolution is undeniable, as chopping her locks off seemingly allowed young Jolie to have more fun with her fashion choices. Metallic and glitter gowns became her go-to choices, but the actor always ensured she added subtle grungy aesthetic to her look — even if it was for a formal occasion. Jolie was allowing herself to play around with clothing to figure out what she likes, and her experimentation phase was nowhere near over.

The early 2000s were definitely one of Angelina Jolie's most memorable fashion eras. By 2000, Jolie had divorced Jonny Lee Miller and married Hollywood star Billy Bob Thornton, 20 years her senior. Categorized by the media as a rather wild coupling, Angelina and Thornton were known for their public displays of affection as well as the vials of each other's blood they carried around their necks. The relationship, as well as becoming a blockbuster star thanks to starring in 2001's "Lara Croft: Tomb Raider," resulted in Angelina's exploration of campy fashion, often surprising fans and the media with her red-carpet choices. 

One of the other most memorable fashion moments of the era was undeniably the Morticia Addams-esque look she wore to the Academy Awards in 2000. In a black, long-sleeved dress by Gucci and with ultra-long black hair extensions, Angelina was exuding mystery and a dash of danger. Meanwhile, her more Lara Croft-inspired looks from the time simply became Angelina Jolie outfits that just didn't work. Speaking to Cosmopolitan in 2003, Angelina said, "Figure out who you are separate from your family and the man or woman you're in a relationship with. Find who you are in this world and what you need to feel good alone. I think that's the most important thing in life. Find a sense of self because with that, you can do anything else." It's an ethos she's certainly adopted in her unique sense of style.

Privately, Angelina was ready for yet another big change, and in 2002, she adopted her first child, Maddox Chivan Jolie-Pitt. Once she split from Thornton later that year, she sought full custody of him.

In 2003, Angelina Jolie's divorce from Billy Bob Thornton was finalized, and while her style continued to have edgy elements, a subtle change towards classic and glamorous fashion was noticeable. While filming "Mr. & Mrs. Smith" that year, Angelina fell in love with her co-star and Hollywood heartthrob Brad Pitt, who was famously still married to actor Jennifer Aniston at the time. Pitt and Aniston divorced in 2005, while Angelina adopted her second child, Zahara Jolie, who is all grown up today, that year. The 2005 premiere of "Mr. & Mrs. Smith" provided yet another iconic Angelina fashion moment, as the star showed up to the red carpet in a perfectly tailored Versace leather dress that undeniably cemented her as a glamorous fashion icon who still loves a dash of the punk aesthetic.

In 2005, Angelina also collaborated with the brand St. John, and she revealed her go-to fashion categories for building her wardrobe. "I am a working mother who has set goals to accomplish a lot in this world," the actor revealed in a statement (via ABC News). "I want my wardrobe to be beautiful, sexy and comfortable — all at the same time. St. John is all of those things." Pitt legally adopted both Maddox Jolie-Pitt and Zahara in 2006, the same year Angelina gave birth to their first biological child, Shiloh Jolie.

In 2007, Angelina Jolie adopted her fourth child, Pax Thien Jolie-Pitt, and a year later, she gave birth to twins Knox Léon Jolie-Pitt and Vivienne Marcheline Jolie. Angelina's maternity fashion was simple and glamorous, always allowing her natural beauty to shine. For the "Kung Fu Panda" premiere at the Cannes International Film Festival in 2008, a very pregnant Angelina stunned in a breathtaking olive-green dress by Max Azria.

A year later, the actor made headlines after showing up to the SAG Awards in another Max Azria dress, which she was wearing backwards. "I don't think too much about what to wear on the red carpet. I usually have three basic colours and I get the same shapes in different colours," she admitted (via Cosmopolitan). "But I like to get dressed up and feel like a lady every once in a while." Speaking of Angelina's pregnancy fashion choices, the star's stylist Jen Rade said they were "soft, sexy, and romantic" (via People).

In 2011, Angelina Jolie collaborated with the brand Louis Vuitton for its "Core Values" campaign, which was shot by esteemed photographer Annie Leibovitz. To no one's surprise, Jolie donated all earnings from the campaign to charity. The following year, she put the internet in a frenzy with both her engagement to Brad Pitt and her Atelier Versace gown for the Academy Awards. While the dress was a simple black strapless gown with an asymmetrical neckline, it was the thigh slit on one side — as well as the way that Jolie carried it — that turned the moment into fashion history. Speaking of the moment in 2019, Jolie told Extra, "There's a whole longer story behind that. I had a more complicated dress and I wore the more comfortable dress, which was that one, and I think I was just so comfortable that ... I think when you feel comfortable, when you feel yourself, you embrace it. And sometimes, maybe it appears to be a thing, I don't know."

In 2012, "Project Runway" star and editor-in-chief of Elle Nina Garcia discussed what Jolie's wedding dress choice might be. "She wears a lot of Versace, but I also think she looks very good in Michael [Kors]," Garcia explained (via E! News). "There's something very easy. She seems to be very not fussy. I don't expect her to wear anything lacy or anything too romantic. I think it will be more streamlined and sleek." As simple silhouettes became Jolie's statement look, we're not surprised Garcia believed she would go for one on her big day, too.

While Angelina Jolie had quite a few stunning fashion moments in 2014 — her tailored Saint Laurent pantsuit for the BAFTAs instantly comes to mind — it was undeniably the "Maleficent" star's wedding dress that most remember first. Jolie and Brad Pitt got married in August 2014 in a private ceremony in France, and the bride's dress was as Nina Garcia predicted: simple, classic, and perfectly tailored to the A-lister.

The dress was designed by Atelier Versace, and the silk material perfectly captured the light with every movement Jolie made. While the dress was stunning, it was the unique veil that actually stole the spotlight. It's no secret that the star adores her family, and while Angelina Jolie and Brad Pitt's kids have changed a lot through the years, their mother's wedding veil remains a reminder of their childhood. The Hollywood star had all of her children's drawings embroidered onto the veil, creating a magical fashion moment that serves as a reminder of how fashion can mean so much more than just fabric and cuts. Speaking to People, Jolie revealed that creating the dress with Versace's tailor Luigi Massi was a wish come true. "Luigi is like family to me and I couldn't imagine anyone else making this dress," she explained. "He knows and cares for the children, and it was great fun putting it together."

As she entered her 40s in 2015, it was clear that Angelina Jolie had her signature style, and her era of exploring various aesthetics was over. Now, the Hollywood actor was all about streamlined and simple cuts and neutral colors. In fact, most of the fashion Jolie wore in the mid-2010s was timeless rather than blindly bowing to trends, allowing the star's stunning beauty to always take the forefront.

Privately, 2016 was a challenging year for the actor as she separated from her husband and father of her children, Brad Pitt. Perhaps because she and her children were going through so many changes, Jolie consciously decided to take a simpler approach to her red-carpet looks, allowing her to shift her focus to where it was more needed.

By 2017, Angelina Jolie was ready to have some fun with her look again; however, her love for timeless fashion remained. One combination that the actor seemed particularly fond of at the time was a silky silver/champagne dress that reflected the light beautifully, paired with a makeup classic: a red lip. Of course, determining which shade of red lipstick is perfect for your skin tone is crucial when pulling this look off — but luckily, Jolie already has all the knowledge she needs. Without the pop of red, the dresses would have potentially washed the actor out, but with it, they undeniably turned into memorable red-carpet moments.

Jolie obviously has a natural knack for fashion, but that year, she revealed that aesthetics are far from the most important thing young women should pursue. "Your intelligence is everything," she revealed during a 2017 talk to promote her film "First They Killed My Father," per Elle. " ... you know, the woman that spends her day shopping is going to be that woman. And the woman that spends her day reading and traveling and learning and talking to people is going to be that woman. And that's the woman you really want to be [the second one]. I think we have to encourage young women to know that, because they're getting fed a lot of the other."

For Angelina Jolie, 2019 was a great fashion year. The actor starred in "Maleficent: Mistress of Evil," the sequel to the 2014 fantasy film, and for the project's press tour, Jolie decided to take a method-dressing approach. In fact, at the time, method dressing started to become the thematic red-carpet trend we still want to see more of. Jolie undeniably drew inspiration from the character she portrayed when picking her signature look for the era, which typically exuded darkness, mystery, and magic.

While picking our favorite of her press tour looks is a tough task, we have to acknowledge the admirable craftsmanship that went into the gown she wore for the premiere of the film in London, England. The actor wore a light-silver dress by Ralph & Russo, one that featured delicate embellishments over its top half as well as eye-catching golden corset-like detailing. With its enhanced pointy shoulders and cape-like design, the gown looked like it belonged in the film. I's clear that Jolie knows plenty about fashion, but 2019 proved that the star is also an expert at the method-dressing trend.

Once life moved on after the COVID-19 pandemic, Angelina Jolie was ready to explore some new looks. Still loyal to classic silhouettes and minimalist accessories, the actor embraced metallics and, every now and then, a bright color. In 2021, she showed up to the premiere of her film "Eternals" at the Rome Film Fest in a dazzling metallic Atelier Versace piece that definitely fit the project's vibes. Angelina attended the event with her daughters, Shiloh Jolie and Zahara Jolie, who are also young fashionistas (and among the celebrity kids who borrow iconic vintage outfits from their famous parents).

Speaking of Shiloh, in October 2021, Angelina and her daughter were spotted attending the "Eternals" premiere afterparty in London, England. The Hollywood star's choice of clothing for the outing definitely surprised anyone who has been keeping up with Angie's style. She opted for a bright-green kaftan, which was definitely an odd color choice for the "Maria" actor, who is known to prefer muted and neutral shades. However, we have to admit that whether she is a fan of bold hues or not, this particular green looks great on her. It was also perfectly timed with the Bottega green wave that took over the fashion world in the early 2020s.

Even though Angelina Jolie dabbled in fashion collaborations here and there, no one really expected the star to start a project of her own. With all the humanitarian work she's involved in, as well as being a mother and a major Hollywood star, it's hard to imagine that Jolie would have time to start a fashion business. But nonetheless, in 2023, the actor launched Atelier Jolie, a creative collective with a focus on fashion.

"I've never been to a fashion show or Met Ball my entire life," she told WSJ that year, revealing that her focus was always on "individuality and freedom." In fact, Jolie herself admitted that she didn't expect the project to turn into a gold mine: "I'll probably lose money, maybe even for a while. If I can eventually put into practice some things that I think are improvements and I just break even, that's a huge victory." Speaking of her personal style, Jolie said, "My daughter jokes that I wear too many trench coats." 

In an interview with Vogue, Jolie admitted that she still doesn't truly know what she likes when it comes to fashion. "Now I wonder if I don't know what my style is because I'm still understanding who I am at 48," the actor explained. "I guess I'm in transition as a person." Whether she believes she has found her style or not, there's no denying that plenty of Jolie's fashion choices have inspired others. In 2024, the actor showed up to the Tony Awards in an eye-catching teal gown by Versace — a design and color that not many could pull off as effortlessly as she did.

Today, Angelina Jolie is known as one of the few Hollywood stars whose style not only changed authentically, but also slowly and with purpose. Jolie has always been known as an advocate for being yourself, and her fashion perfectly reflects that. "My house is very, 'To each their own,'" she admitted to E! News in 2025. "We're very democratic. Everybody does their own thing. As long as you're being you, we're good," the actor explained. "If you're dressing up to try to impress somebody else or be like somebody else, we would probably just call you out. But if you're you, be you!"

"What makes her fashion evolution so compelling is that she hasn't chased trends, she's built a wardrobe language that's entirely her own," Megan Watkins told Hello! in 2025. "When Angelina steps onto a red carpet, you're not just seeing a beautiful dress, you're seeing consistency, control and a woman completely in command of her image." As Jolie entered her 50s, her fashion is timeless yet fun, both simple and intricate, but most of all, undeniably authentic. And frankly, we can't wait to see what looks she blesses us with in the next decade!

If you love dissecting that style of gorgeous and influential Hollywood legends, be sure to also check out Sofia Coppola's stunning style transformation!