Happy birthday, Angelina Jolie! One of the biggest movie stars of our time turns 45 on June 4, 2020, and in honor of the superstar's big day, Wonderwall.com is taking a look back at how she's transformed over the years. From wild child to mother of six to sophisticated style queen, keep reading to see the humanitarian and Oscar winner's changing looks over the years…
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As a teenager, Angelina Jolie rocked long dark hair, as seen here when she posed for a portrait in Los Angeles in 1991. The star — who was just 15 at the time — had yet to embark on her Hollywood career, but the coming years would see the beauty undergo a major transformation.
A few years later in 1994, a then-19-year-old Angelina Jolie rocked a black slip dress with a red lip, a hat and bare feet during a photo shoot. That year, she starred in a few Meat Loaf music videos, but a year later in 1995, she appeared in her first major Hollywood role in "Hackers" alongside Jonny Lee Miller. She married her co-star in 1996, showing up for the ceremony in black rubber pants and a white T-shirt with the groom's name written across it in her own blood. Can you tell we're about to see a much edgier Angelina? That's not the last time we'll hear about her wearing blood either…
Angelina Jolie's career really took off in the late '90s, which is when she also started to show her individual style. Seen here at 21 attending the 1998 Golden Globes, where she picked up her first accolade — a trophy for best supporting actress in a series, miniseries or TV film for her work in "George Wallace" — Angelina looked surprisingly demure. She sported a super-short hairstyle and a super-sparkly column dress with a shawl draped over top.
For Angelina Jolie, 1998 was a big year. She's seen here at the 50th Annual Primetime Emmy Awards in September 1998 wearing a gold-hued gown with delicate crystal embellishments. That night, she was nominated for two awards — outstanding lead actress in a limited series or movie for her work in "Gia" and outstanding supporting actress in a limited series or movie for her performance in "George Wallace."
In 1998, playing model Gia Carangi in the HBO film "Gia" would help catapult Angelina Jolie to stardom, but she also took on some more commercial roles, including in "Playing By Heart," an ensemble flick that also starred Ryan Phillippe, Jay Mohr, Gillian Anderson, Gena Rowlands and more. Angie arrived at the premiere that December in this mature, polished look — a white dress underneath a tailored tan coat.
Angelina Jolie took home the Golden Globe for best actress in 1999, winning for her performance as the late AIDS-afflicted model Gia Carangi in "Gia." As she joined the ranks of the Hollywood elite, Angelina started to dress the part, selecting this dazzling Randolph Duke creation for the Globes ceremony. The slinky design featured plenty of sparkling embellishments, making her look like a statuette herself. But not long after this, her style started to get a whole lot darker…
Fresh off a finalizing her divorce from Jonny Lee Miller, Angelina Jolie debuted a much more gothic getup at the 2000 Academy Awards. Her Elvira-like ensemble was the work of designer Marc Bouwer. She won a best supporting actress Oscar at the ceremony that night for her work in "Girl, Interrupted." During her speech, she memorably gushed, "I'm so in love with my brother right now," which raised eyebrows at the time, as did the way they kissed each other on the lips.
2001 was another strong year for the actress! Just five months before making her debut as video game heroine Lara Croft in the action flick "Lara Croft: Tomb Raider," Angelina Jolie attended the 58th Annual Golden Globe Awards in Los Angeles. This sleek, strapless champagne-hued dress was a departure from the all-black ensembles she'd frequently sported the year prior.
And she's back! The edgy, goth looks Angelina Jolie favored at the turn of the millenia returned later in 2001. Seen here at the "Tomb Raider" premiere in 2001, Angelina Jolie rocked straight jet-black hair, a black tank top and a pair of leather pants that showed some of her many tattoos.
Angelina Jolie was just shy of her 25th birthday when she married for the second time, this time tying the knot with Oscar winner Billy Bob Thornton, who's nearly 20 years her senior. Their romance reached its eccentric peak in July 2001 when they attended the premiere of her film "Original Sin" together. Though her fitted white dress didn't seem unusual, her choice of accessories did: The actress had a vial of Billy Bob's blood hanging from her neck — and he had a vial of hers dangling from a necklace of his own!
Angelina Jolie started to look more mature after adopting son Maddox in March 2002 and diving into humanitarian work. She's seen here at the launch of World Refugee Day in Washington, D.C., in June 2002 in a very simple three-quarter-sleeved black dress, which was worlds away from her previous tattoo-baring leather ensembles.
For the premiere of the second "Tomb Raider" installment, "Lara Croft: Tomb Raider — The Cradle of Life," in July 2003, Angelina Jolie didn't channel her character again. Instead, she kept things more in line with her new subdued style. Though the floor-length dress she wore was in her signature hue — black — it featured a flowing skirt and feminine sleeves.
The early 2000s saw Angelina Jolie's popularity rise to new levels — and her bombshell status skyrocketed too. The star exemplified the epitome of Hollywood beauty at the premiere of her film "Beyond Borders" in Madrid in October 2003. She donned this beautiful light green halter gown with her brown locks down in loose waves. It was also the first time we saw the star rock a thigh-high slit… which we'd memorably see again years later!
Angelina Jolie attended the premiere of "Sky Captain and the World of Tomorrow" in Los Angeles in September 2004 in this simple, sophisticated look. The beauty paired an ivory slipdress dotted with tiny crystal embellishments with a pair of ruby-red heels and a matching red clutch. She kept a low profile romantically that year — her divorce from Billy Bob Thornton had just been finalized in 2003 — but she'd also started filming "Mr. & Mrs. Smith" alongside Brad Pitt…
Angelina Jolie, the other woman? The actress showed up in this pretty, colorful silk halter dress printed with geometric designs for her first "Mr. & Mrs. Smith" press appearance with Brad Pitt in March 2005, which made her look far more innocent than many media outlets were making her out to be. At the time, the superstars — who kept their distance publicly — were in the midst of a pretty major scandal: In January, Brad announced his split from wife Jennifer Aniston amid rumors that Angelina was behind the breakup. A month after this photo was taken, Brad and Angelina were photographed on a beach in Kenya with her son Maddox, essentially confirming that they were indeed a couple.
Angelina Jolie paid homage to her old style at the "Mr. & Mrs. Smith" premiere in Los Angeles in June 2005 when she arrived rocking this slinky leather halter dress by Versace. Though she and Brad Pitt had yet to officially confirm their romance, the next month saw them flying to Africa to adopt Angelina's second child, daughter Zahara, from Ethiopia.
While pregnant with her first biological child with Brad Pitt, Angelina Jolie dressed demurely while attending an event during the World Economic Forum in Davos, Switzerland, in January 2006. The star wore a matching gray skirt, top and sweater set that also showed off her baby bump. Daughter Shiloh arrived four months later.
A year after giving birth to Shiloh — and two months after adopting son Pax from Vietnam — Angelina Jolie rocked one of her all-time best red carpet looks in May 2007 during the Cannes Film Festival. The star attended the premiere of "Ocean's 13" in this stunning canary yellow Emanuel Ungaro number that featured spaghetti straps and a beautiful, flowing skirt. It marked one of the rare moments the superstar opted to hit a red carpet wearing a vibrantly colored confection. One of her other brightest frocks is up next…
What a difference a year makes! Angelina Jolie, who was pregnant with twins at the time, attended the "Kung Fu Panda" premiere during the Cannes Film Festival in May 2008 in this fabulous, vibrant green Max Azria Atelier gown. Two months later, she and Brad Pitt welcomed twins Vivienne and Knox.
Just three months (yes — only three!) after welcoming twins Vivienne and Knox, Angelina Jolie was back on the red carpet, this time at the premiere of her film "Changeling" in New York City in October 2008. For the occasion, she opted for a form-fitting strapless Versace dress that showed off her incredible post-baby body.
A softer side of Angelina Jolie! She spent most of 2009 in her standard black, but for the premiere of her action flick "Salt" in London in August 2010, Angelina opted for this pale pink-and-silver sequined bohemian number by Amanda Wakeley. This look ushered in an era of Angelina rocking her medium-brown hair in waves and opting for dresses in softer shades.
Angelina Jolie kept with paler hues in 2010 — though she sported some bigger hair — donning this off-white Atelier Versace design with a thigh-high slit at the premiere of "The Tourist" in New York City that December. The flick, which co-starred Johnny Depp, earned her a Golden Globe nomination but was panned by critics. Still, it did surprisingly well at the box office.
A bold look! At the 2011 Golden Globe Awards, Angelina Jolie wore a gorgeous long-sleeved emerald green gown by Atelier Versace — a departure from the muted tones she'd donned a year prior. The actress, who was just five months shy of her 36th birthday, was nominated for best actress in comedy or musical film for her work in "The Tourist."
In 2012, Angelina Jolie gave fans a pop of color at the 69th Annual Golden Globe Awards, stunning in a white-and-red gown by Atelier Versace. Her matching red lipstick and clutch, along with her simple accessories and sleek bun, were gorgeous finishing touches to this classy look. That evening, Angelina presented the best director award — she'd made her own directorial debut one month earlier in December 2011 with the film "In the Land of Blood and Honey."
Versace dressed Angelina Jolie for another one of her iconic red carpet moments — one that launched a thousand memes! The star walked the 2012 Academy Awards red carpet in this strapless velvet confection in her signature black hue that featured a thigh-high slit that allowed for a major leg-pop moment. Her red lip and big waves cemented this as a glam Hollywood look, which was notable as it came in the midst of her nearly three-year absence from the big screen.
A supportive partner! In 2013, Angelina Jolie joined then-fiancé Brad Pitt at the German premiere of his film "World War Z" in Berlin. Ralph & Russo dressed the star for the international occasion — she looked futuristic in her white peplum dress with metallic detailing around the waist.
2014's "Maleficent" marked Angelina Jolie's return to the big screen! Her Los Angeles premiere look that May — another dramatic strapless black gown by Atelier Versace — epitomized her style of the moment with its shiny rubberized silk aesthetic and glamorous gathered train. The look also jived with her on-screen character.
Angelina Jolie pushed the sartorial parameters yet again at the 2014 BAFTA Awards, where she looked classy yet cool in a menswear-inspired tuxedo by Yves Saint Laurent.
For the November 2014 premiere of "Unbroken," which she directed, Angelina Jolie took a cue from her philanthropic wardrobe, opting for a cream Ralph & Russo pencil dress topped with a bolero-style cape. The event came a few months after she and Brad Pitt quietly tied the knot in August 2014. This look ushered in a period of a more conservative, demurely styled Angelina, which continued for a few years…
When it came time for the premiere of her second directorial effort, the November 2015 film "By the Sea" (in which she also co-starred alongside husband Brad Pitt), Angelina Jolie once again tapped Versace for an outfit. She selected this super-simple strapless ivory dress, no doubt hoping to keep the attention on her work and not her wardrobe.
Previously, the words "Angelina Jolie" and "pleated ballgown" never would have appeared in the same sentence, but in this new era of polished, refined Angelina style, the combo seemed to suit her perfectly. The star sported this strapless plum Dior confection at a "First They Killed My Father" screening — she wrote and directed the project — in September 2017. The appearance came a year after she suddenly and surprisingly split from Brad Pitt and filed for divorce.
Angelina Jolie hit the Critics' Choice Awards in January 2018 in an unexpectedly whimsical look — a super-fun strapless white custom frock by Ralph & Russo complete with some very major feather detailing along the bodice. She expertly added silver pointy-toe heels and her signature red lip.
In June 2018, to commemorate the 200th anniversary of the Order of St. Michael and St. George, Angelina Jolie attended a special ceremony at St. Paul's Cathedral in London. The star wore a prim dove gray ensemble by Ralph & Russo complete with a matching fascinator and gloves — and accessorized with the Order of St. George and St. Michael brooch that she received when Queen Elizabeth II in 2014 appointed her an honorary Dame Commander for her humanitarian work.
2018 marked the beginning of a more ethereal-looking Angelina Jolie — and we were absolutely here for it. At the 32nd Annual American Society of Cinematographers Awards, the actress-director looked breathtaking in a sheer metallic Elie Saab gown with delicate embellishments. That evening, she was the recipient of the 2018 ASC Board of Governors Award, which recognizes people who have made outstanding contributions to film.
Angelina Jolie continued to stun sartorially in 2019. While promoting "Maleficent: Mistress of Evil" at Hotel De La Ville in Rome that October, she was a pastel vision in this lilac and lavender pleated top by Givenchy Haute Couture, which she wore over black trousers and heels.
From daytime to evening! While she sported a memorable pastel-colored Givenchy Haute Couture piece earlier in the day, Angelina Jolie embraced the dark side for her evening look. She's seen here at the European premiere of "Maleficent: Mistress of Evil" wearing a custom black gown by Atelier Versace covered in delicate micro sequins. The fitted strapless number echoed Angelina's sexy and sleek looks from award shows past.
And the enchanting ensembles continue! As she carried on with her European press tour promoting "Maleficent: Mistress of Evil" in the fall of 2019, Angelina Jolie looked like a goddess at the film's London premiere in a glistening beaded dress with a gold cage bodice and a dramatic flowing cape by Ralph & Russo Couture. From the metallic shoulders to the silver and gold paillettes, beads and chains, the gown was absolutely spellbinding.