Angelina Jolie's Most Inappropriate Outfits

Angelina Jolie has been one of Hollywood's biggest stars for decades, meaning she's had plenty of time and opportunities to showcase her fashion choices to the world. While the star is mostly busy with her humanitarian work and six children, she found the time to delve into the world of fashion with her eco-friendly business venture. The sustainable initiative is aimed at providing a platform for young creatives and repurposing clothes, but Jolie does have a penchant for fashion when it comes to her personal style, too.

Known for her minimalistically chic approach, Jolie admitted that she likes to play it safe in terms of fashion. "I invest in quality pieces and then just wear them to death," the star told Vogue in 2021. "Boots, a favorite coat, a favorite purse; I don't change things often, you know? That's one of my things." It actually is, because Jolie's been riding the minimalist style wave for years now, despite her earlier affinity for an undoubtedly wilder aesthetic. "I was a punk. I loved leather, PVC, and fishnets. Those were my three favorite fabrics in my early 20s," Jolie shared when speaking to Harper's Bazaar in 2019.

Despite sticking to what she knows best and rarely switching up her style, Jolie has not been immune to occasional fashion missteps. While some of them happened in the early days of her career, more have — surprisingly — come from her sleek style phase.

Her slit-ridden dress was a bit much for a movie premiere

Angelina Jolie's love for daring slits is nothing new, but it was only a matter of time before a fashion faux pas occurred with such a boldly revealing approach. At the 2010 Japan premiere of Jolie's action movie "Salt," the star opted to wear a black floor-length gown with a high neck by Atelier Versace. With an abundance of dark fabric, multiple openings were incorporated into the dress, undoubtedly to make the piece more attractive. Featuring an extreme thigh-high slit, an entirely open back, and even a shoulder slit, the ensemble was undeniably provocative — perhaps too much.

While Jolie herself looked stunning, her gown was more suited for a party than a premiere. The numerous large cut-outs gave the impression of an unfinished garment, while the seeming chiffon fabric added a flowy movement to the already dangerously exposing dress, putting Jolie at risk of baring much more than she bargained for.

Other than not quite being the most appropriate choice of attire for a movie premiere, Jolie decided to pair her slit-ridden gown with an updo hairstyle and tiny dangling earrings. While the combination would have otherwise been a winning one, paired with the high neck of the dress, it only made Jolie look confusingly conservative on top.

The actor's rock ensemble missed the red carpet mark

One of the most obvious aspects of Angelina Jolie's stunning transformation was undoubtedly her change of style. Before she became a fan of oversized garments and flowy dresses, Jolie was synonymous with a rock-inspired aesthetic that mirrored her wild lifestyle. Not even a red carpet event like the premiere of her own movie could've stopped the star from staying true to herself, as evidenced by her choice to wear leather pants and a tank top to one.

In 2001, at the Los Angeles premiere of "Tomb Raider," Jolie made a bold statement with an outfit anybody else would've likely worn to run errands or grab a cup of coffee with friends. The actor paired her black leather pants and black top with pointed-toe heeled leather boots in, you guessed it, black. She accessorized with a black leather belt with studs, opting for no jewelry and no bag.

Again, while Jolie's inherent charisma tends to shine through regardless of what she's wearing, this particular choice of attire was simply not appropriate for the grandeur of a movie premiere. Granted, the early 2000s were a different time in terms of fashion, even when it came to red carpets, but as the movie's lead, Jolie could have at least added some bling to elevate her ensemble.

Jolie took her goth aesthetic a step too far in the costume direction

The 2000 Oscars were one of the most iconic in the history of the awards ceremony, at least for Angelina Jolie. Other than being the first of the new millennium, the show marked a significant moment in Jolie's career as she won her first Academy Award for her supporting role in "Girl, Interrupted." In addition to realizing the achievement of a lifetime, Jolie also infamously kissed her brother, James Haven, later in the evening. Despite all this, Jolie's outfit somehow managed to steal the spotlight, but not in the best of ways.

The actor went with a floor-length black gown with long sleeves, designed by Marc Bouwer. Her shoes weren't visible most of the evening as the dress was so long (don't be mistaken, they were black), and she didn't carry a bag. Opting for a gothic vibe, Jolie let her long, jet-black hair cascade down to her hips, leaving her looking like none other than Morticia Addams.

The overall dark aesthetic was accentuated by bold cat-eye makeup and very minimal jewelry, which gave Jolie a vampire-like appearance. While many consider this look iconic, especially in terms of Jolie-specific fashion, the entire ensemble had a somewhat theatrical quality, more reminiscent of a costume than an Oscar-worthy look.

She once looked like she was going to the office instead of a photocall

It's evident that Angelina Jolie will stick to her fashion choices no matter the occasion or prevailing trends of the moment. Following her goth and rock phases, the star's minimalistic preference overtook her style expression throughout the years, and she has no problem showcasing it to the world regardless of the nature of the event she's attending.

In 2007, during a photocall for "A Mighty Heart" at the Cannes Film Festival, the actor showed up wearing an outfit more suited for a 9 to 5 job. While she might've been listening to Dolly Parton a lot at the time, nothing can warrant her choice of such lifeless attire while promoting her own project. The actor wore a fitted midi-length skirt in black, which she paired with a brown, short-sleeved silk blouse cinched at the waist. She completed the look with black open-toe pumps and notably wore no jewelry — not even a single ring. Her hair was styled in a half-updo, and her makeup was kept subdued and classic.

While Jolie's look wasn't necessarily bad per se, it failed to meet the more elevated expectations of a Cannes photocall. Again, the fashion landscape of the 2000s was vastly different than it is today, yet Jolie's choice still fell flat, even for the era in which it was executed.

Another one of Jolie's red carpet looks left much to be desired

Angelina Jolie is no stranger to serving looks on the red carpet, but some of her outfits were so understated that, if you didn't know who she was, you'd likely think she was an event staffer rather than one of Hollywood's biggest stars.

As she appeared at the 2016 premiere of "Kung Fu Panda 3," wherein she reprised her voice role for the third time in the animated film series, Jolie looked like she was attending a funeral more than anything else. The actor wore a short-sleeved black mini dress by Saint Laurent and black leather pumps from the same fashion house, proving that minimalism has replaced her glam rock aesthetic for good. Admittedly, it was the premiere of a children's movie, but Jolie still looked completely out of place in her all-black ensemble.

Adding to the solemn vibe, the star kept her hair and makeup simple, opting to accessorize with subtle jewelry and a single piece of red string tied around one of her arms. Empty-handed, Jolie looked a tad disconnected amid the vibrant surroundings, which further highlighted the understated feel of her outfit.