Angelina Jolie turns 48: From wild child to Oscar winner and activist

To celebrate Angelina Jolie’s 𝐛𝐢𝐫𝐭𝐡day on June 4, Wonderwall.com is taking a look back at her transformation over the years from Hollywood wild 𝘤𝘩𝘪𝘭𝘥 to Oscar winner to activist and mother of six. Let’s start with this stunning 1991 portrait of the brunette beauty, who was 𝐛𝐨𝐫𝐧 in 1975 to actors Jon Voight and Marcheline Bertrand and made her acting debut alongside her dad in 1982’s “Lookin’ to Get Out.”

A few years later in 1994, a then-19-year-old Angelina Jolie looked all grown up in a black slip dress with a red lip, a hat and bare feet during a photo shoot. By that point, she’d branched further into acting by appearing in music videos.

Angelina Jolie rocked an edgy pixie cut and bold electric blue eye makeup for her role in the 1995 crime drama “Hackers,” which marked her first big breakthrough as an actress. The following year, she married co-star Jonny Lee Miller in black rubber pants and a white T-shirt with his name written across the chest in her own blood. 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 also when she started to really embrace her own unique sense of style. Seen here at 21 attending the 1998 Golden Globes, during which she picked up her first big award — 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 midi-length dress with a shawl draped across her shoulders.

It was a big year for Angelina Jolie. During the 1998 Emmy Awards, the actress channeled an Emmy statuette by wearing a gold column gown. She was up for two awards that night: 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.”

Portraying troubled beauty Gia Carangi in the HBO made-for-TV movie “Gia” helped launch Angelina Jolie to superstardom. During the 1999 Golden Globes, she won the award for best actress in a miniseries or TV movie for her work in the 1998 biopic. Angelina donned a dazzling Randolph Duke creation worthy of the stunning supermodel for the occasion. Not long after this, however, her style started to get a whole lot darker…

During the 2000 Academy Awards, Angelina Jolie — who was fresh off finalizing her divorce from Jonny Lee Miller at the time — debuted her new goth-inspired aesthetic while channeling Elvira in a black Marc Bouwer creation. She won the Oscar for best supporting actress for her work in “Girl, Interrupted” that night and memorably gushed during her acceptance speech, “I’m so in love with my brother right now.” Her comment about big bro James Haven certainly raised eyebrows … as did the way they kissed on the lips while celebrating her big win.

Following her goth phase, Angelina Jolie started taking style cues from her on-screen alter ego in 2000’s “Gone In 60 Seconds” — car-thieving mechanic Sway. (She also memorably rocked long blonde locks for the action flick.) See what we mean next…

Angelina Jolie went full biker-chic in leather pants and a cropped tank that showed off her abdominal tats during the 2001 premiere of “Lara Croft: Tomb Raider.” (Her on-screen alter ego would certainly approve of this ensemble.) The action flick was a huge hit at the box office — her biggest at the time!

Angelina Jolie was just shy of her 25th 𝐛𝐢𝐫𝐭𝐡day when she married second husband Billy Bob Thornton, who’s nearly 20 years her senior, in May 2000. Their romance reached its eccentric peak in July 2001 when they attended the premiere of her film “Original Sin” together. Her fitted white dress was pretty but nothing to write home about. Her necklace, however… The actress and her hubby infamously wore vials of each other’s blood around their necks.

Angelina Jolie adopted a more mature look after she adopted son Maddox in March 2002 and dived into humanitarian work. In June 2002, for example, she wore a simple black dress — worlds away from the tattoo-baring leather ensembles she regularly sported in previous years — during the launch of World Refugee Day in Washington, D.C.

There was no channeling Lara Croft this time! When Angelina Jolie attended the premiere of sequel “Lara Croft: Tomb Raider — The Cradle of Life” in July 2003, she kept things more in line with her new subdued sense of style. Although she stuck to her signature shade — black! — her floor-length dress featured some unexpectedly feminine details like flowing sleeves and a skirt with ruching at the hips.

The early 2000s saw Angelina Jolie’s popularity — and her bombshell status — skyrocket! She exemplified Hollywood glam in a gorgeous green grown with a thigh-high slit that showed off one of her tanned gams at the premiere of her film “Beyond Borders” in Madrid in October 2003.

Speaking of Hollywood glam… Angelina Jolie channeled Old Hollywood in a stunning Marc Bouwer gown with a plunging neckline during the 2004 Academy Awards.

Angelina Jolie was the epitome of California cool in a silk halter dress featuring a colorful geometric design during her first “Mr. & Mrs. Smith” press appearance with Brad Pitt in March 2005. The effortless look certainly made her appear more innocent than many media outlets were portraying her at the time as she and her comely co-star navigated a pretty major scandal: That January, Brad and first wife Jennifer Aniston called it quits amid rumors he and Angelina had an affair. A month after this photo was taken, Brad and Angelina were photographed on a beach in Kenya with her son Maddox, essentially confirming they were, in fact, a couple.

Angelina Jolie paid homage to her old sense of style at the “Mr. & Mrs. Smith” premiere in Los Angeles in June 2005 by rocking a curve-hugging 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.

Angelina Jolie dressed demurely at the World Economic Forum in Davos, Switzerland, in January 2006. The actress — who was pregnant with her first biological 𝘤𝘩𝘪𝘭𝘥 with Brad Pitt at the time — 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 during the 2007 Cannes Film Festival. The actress attended the premiere of “Ocean’s 13” in this stunning canary yellow Emanuel Ungaro number that featured spaghetti straps, a draped bodice 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 2008 Cannes Film Festival in this fabulous, vibrant green Max Azria Atelier gown. Two months later, she and Brad Pitt welcomed twins Vivienne and Knox.

In October 2008 — just three months (yes, three!) after welcoming twins Vivienne and Knox — Angelina Jolie made her return to the red carpet at the premiere of her film “Changeling” in New York City. She flaunted her incredible post-𝑏𝑎𝑏𝑦 body in a curve-hugging strapless Versace dress.

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, the actress 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 stuck to 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. She earned a Golden Globe nomination for her work in the action flick, which co-starred Johnny Depp and tanked with critics.

A bold look! During 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. She was up for best actress in comedy or musical film for her work in “The Tourist” that year.

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.”

A supportive partner! In 2013, Angelina Jolie joined then-fiancé Brad Pitt at the German premiere of his film “World War Z” in Berlin. She rocked wedding white for the occasion, donning a futuristic Ralph & Russo dress with a peplum waist cinched by metallic panels. They tied the knot the following year.

Angelina Jolie made her big return to the big screen with 2014’s “Maleficent.” During the Disney flick’s Los Angeles premiere that May, the actress donned another strapless black gown by Atelier Versace. Her on-screen alter ego surely would’ve approved of the dramatic leather dress, which featured a glamorous gathered train.

Angelina Jolie pushed the sartorial parameters yet again at the 2014 BAFTA Awards. She looked classy yet cool in a menswear-inspired tuxedo by Yves Saint Laurent.

Perhaps as a nod to her August 2014 nuptials with Brad Pitt, Angelina Jolie wore white to the November 2014 premiere of “Unbroken,” which she directed. The multi-hyphenate looked sophisticated in a cream Ralph & Russo pencil dress topped with a bolero-style cape. This look ushered in a period of a few years during which the actress sported conservative and demure styles.

It was Versace (again!) for Angelina Jolie during the late 2015 premiere of “By the Sea,” which she wrote and directed. She selected this super-simple strapless ivory number for the occasion — no doubt hoping to keep the attention on her work and not her wardrobe. Angelina also co-starred alongside then-husband Brad Pitt in “By the Sea,” which was her final on-camera acting gig for the next four years.

Angelina Jolie donned a pleated plum Dior gown during a special screening of “First They Killed My Father” — which she wrote and directed — in September 2017. It was an appropriately glam yet conservative getup for the Oscar-winning actress, who was focused on her work as a director and on recovering from her 2016 split from Brad Pitt at the time.

Angelina Jolie attended the 2018 Critics’ Choice Awards in an unexpectedly flirty frock: a super-fun strapless Ralph & Russo confection with a feathered bodice. She completed her stunning look with 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. She 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 in 2014 when Queen Elizabeth II appointed her an honorary Dame Commander for her humanitarian work.

Angelina Jolie chose many ethereal looks in 2018 — and we were absolutely here for it! The actress-director looked breathtaking in a sheer metallic Elie Saab gown with sheer overlay featuring delicate embellishments during the 32nd Annual American Society of Cinematographers Awards. That evening, she received the ASC Board of Governors Award, which recognizes individuals who’ve made outstanding contributions to film.

Angelina Jolie continued to stun sartorially in 2019. While promoting “Maleficent: Mistress of Evil” in Rome that October, she went outside of her fashion comfort zone in a pretty purple pleated Givenchy Haute Couture top, which she wore over black trousers and heels.

She’s never looked more regal! Angelina Jolie stunned in a Ralph & Russo creation featuring a caged bodice and a dramatic cape during the London premiere of “Maleficent: Mistress of Evil” in October 2019. From the metallic shoulders to the silver and gold paillettes, beads and chains, the gown was absolutely spellbinding.

In September 2021, Angelina Jolie attended Variety’s Power of Women event in a caramel silk frock from Harithand designer Harith Hashim.

Angelina Jolie’s “Eternals” alter ego, Thena, would approve of this goddess gown — a strapless brown Balmain creation — that the actress donned at the Hollywood premiere of the Marvel movie in October 2021. But it’s one of her accessories that really stole the spotlight…

Edgy! Angelina Jolie sported a Nina Berenato lip cuff that ran down her chin during the Hollywood premiere of “Eternals” in October 2021.

A show-stopper! In October 2021, Angelina Jolie attended the “Eternals” premiere at the Rome Film Festival in a custom Atelier Versace creation. From its body-hugging silhouette to its gorgeous draping, Angie’s metallic mesh gown was one of her most stunning looks to date.