Angelina Jolie Outfits That Just Didn't Work

Actor Angelina Jolie is undoubtedly one of the great icons of modern Hollywood. Her film career has earned her more than 60 industry awards, plus over 120 nominations, and if those work accomplishments weren't enough, Jolie is also known for her gorgeous appearance. On its face, this sounds like the profile of a woman who can do no wrong. However, Jolie has had her hand in several pop-culture kerfuffles and has even made waves with some of her sartorial choices. For example, Jolie is one celebrity who has sometimes missed the mark with method dressing, veering too literal or too off-theme in her quest for a cohesive press run. Occasionally, she's also puzzled onlookers by wearing overly casual and low-key styles to high-profile events.

This all goes to show that even celebrated performers like Angelina Jolie, who have amazing style secrets for us to learn from, aren't above fashion reproach from time to time. From squirming into club-ready leather pants for a film premiere to going shapeless and off-season at a star-studded after-party, Jolie has attempted some outfits that ultimately just didn't work.

The year 2001 was a different time, but even then, there were certain expectations for red-carpet couture. Angelina Jolie ignored them all to embody a spirit of rebellion for her "Lara Croft: Tomb Raider" premiere — a decision we appreciate, but that hasn't stood the test of time. Jolie arrived at the premiere in skin-tight leather pants with a studded belt, sharp black heels, and a belly-baring tank that put her stomach tattoos on display. While Jolie looked good as always, this aggressively edgy look seemed to be riding the millennium's wave of sharp, "Matrix"-like fashion in a way that was nearly costumey. As we've learned from more pitch-perfect instances of method dressing, like Jenna Ortega's "Beetlejuice Beetlejuice" promo looks, the best press-tour 'fits are referential without being so on the nose.

Angelina Jolie isn't completely above the pull of fashion trends, but she usually manages to put her own darkly glamorous stamp on them at least. Cue our bewilderment over the very un-Angelina ensemble she put together for the 2004 premiere of "Shark Tale." Jolie partnered a pair of nonchalant jeans with pointy red shoes and a full-on leopard-print trench, even brushing her hair back and adding a pair of hoops. Was this a super early take on TikTok's mob wife aesthetic that dethroned the clean girl look? Did Jolie get turned around in an early 2000s Ross Dress for Less? Whatever the star's reasoning, this departure from her usual style didn't make a positive impact.

Despite being an A-list actor, Angelina Jolie chose a surprisingly pedestrian ensemble when attending a photo call for her film "A Mighty Heart" at the Cannes Film Festival in 2007. Jolie looked fine in her black pencil skirt, peep-toe heels, and belted brown peasant blouse, but "fine" is a pretty low bar for such a stunning woman, especially while she was trying to promote a new film. This inexplicable styling was so run-of-the-mill that it could nearly be an outfit worn by Pam on "The Office" — or any real-world corporate worker. A missed opportunity, to say the least.

Angelina Jolie has worn her fair share of risqué outfits, but sometimes, her fashion pendulum swings too far in the other direction — for instance, at the 2014 Oscars. Jolie, who was only 38 at the time, chose a classy but curiously demure Elie Saab gown that could have passed for a particularly nice mother-of-the-bride look. Its high neck, long sleeves, and softly cinched waistline all seemed calculated to flatter an older woman, none of which Jolie needed to compliment her natural beauty. Ultimately, this made the gown feel like a bland and forgettable misstep from the "Maleficent" actor.

Minimalism is one thing, but we like to see a little personality on the red carpet. Unfortunately, Angelina Jolie failed to deliver any kind of interest at the Los Angeles premiere of "Kung Fu Panda 3" in 2016. The star's little black dress was dull and expected, and it lacked any notable accessories or design details to elevate the look. The frock's silhouette was painfully straightforward with its cap sleeves and boat neck, and even Jolie's black heels were as basic as could be. Jolie may usually have a reputation as a rebel and risk-taker, but this particular outfit was an example of fashion so safe that it became snooze-worthy.

We're betting that Angelina Jolie was going for timeless and otherworldly when she decided to don a drapey, bright-green kaftan dress for the after-party of the "Eternals" U.K. premiere in 2021. However, the vivid color and loose fit instead seemed like ill-timed resort wear — beachy isn't really the vibe in London in October. Credit where credit is due, Jolie's nude pumps felt like the perfect shoe choice for this outfit, but her typically restrained makeup and utter lack of jewelry — or even a handbag — left the look feeling simplistic to the point of incompletion. Perhaps she eventually meant to CGI a more interesting outfit over this moving green screen?

Now for the positives about everyone's favorite "Maria" actor: Check out these six times Angelina Jolie went nearly makeup-free and looked flawless.