Angelina Jolie Outfits That Completely Missed The Mark

Angelina Jolie is one of the most beautiful women in the world, with a figure that can rock any outfit, but that doesn't mean all of them are winners. The mom of six rose to fame in the '90s with the movies "Foxfire" and "Hackers," and Jolie has undergone a gorgeous transformation since then. At the time, she was known for her goth aesthetic, preferring to wear black — and a lot of it. While she still favors the color, Jolie's look has become much softer, and fans often see her in floaty, breezy materials.

It's easy to look good when you have a host of top-shelf designers and fashion experts at your fingertips. However, Jolie admitted to "WSJ Style" that she doesn't have a go-to stylist. "I don't like the idea of just somebody putting clothes on me or my kids. ... So much clothing is identity," she explained. Unfortunately, that means some of Jolie's choices have been flops, and yes, even the "Maleficent" star has experienced some fashion fails over the course of her career.

Angelina Jolie's latest role is that of the late opera singer Maria Callas, and she made fans do a double take at the film's premiere on October 26 with her new look. Instead of her usual sleek 'do, Jolie wore her honey-colored hair in messy, loose curls around her face. That wasn't the only disheveled thing about her look. The "Maria" star wore a long silky dress from her clothing line, Atelier Jolie, but she didn't do her brand any favors. The bodice was terribly wrinkled, and the geometric panels at the waist created an odd shape. What's more, she had a large black shawl draped over her shoulders, which may have been an attempt to hide all the creases in her dress.

As we all know, fashion faux pas never go unnoticed by the public, and Redditors shared their dislike for Jolie's frock. "I love that she is branching out and trying something new. But this whole hair, outfit, even the thick red lip with this color palette is not it," a fan commented. Another tactfully stated, "Rare miss for Angelina. I don't know how to say this nicely but she looks like she woke up, tore the curlers out of her hair, and threw a jacket over her nightie before jumping in the car." Considering she had worn this particular dress before, one would think Jolie would have known to steam it before the premiere, but alas!

Angelina Jolie has been hard at work promoting "Maria," even risking a run-in with her ex-husband, Brad Pitt, at the Venice Film Festival in August 2024. Thankfully, their appearances were slotted for different times, and Jolie was able to pose freely in her brown Saint Laurent by Anthony Vaccarello gown. Sadly, this look was not picture-worthy, with the dark chocolate color looking completely drab and the overload of draping around her chest area. It looked more like an ill-fitting bridesmaid gown than a high-end creation — but at least there were no wrinkles in sight. One reader commented, "She is a beautiful woman, but that dress does not do her justice. For some reason, she comes across as very high maintenance." Another wrote, "Greek goddess does not come to mind when seeing that dress. It's kind of frumpy looking."

Jolie did much better later at the premiere of "Maria" wearing a more form-fitting Tamra Ralph dress in a beautiful champagne shade. Draped around her shoulders was a matching faux fur shawl with a floral pin. Now this is what we call "Hollywood glamor."

Angelina Jolie occasionally rocks some very risqué outfits, but she decided take a more playful route in a feathered dress by Ralph & Russo Couture at the 2018 Critics' Choice Awards. It wasn't just a sprinkle of fluff here and there — the entire top part of the frock was laden with feathers, so much so that it looked like an ostrich had exploded. We seriously don't know how Jolie was able to pose in front of the cameras without sneezing.

It seems as if the "First They Killed My Father" director was on a serious feather kick around that time. She had previously worn a sheer black Atelier Versace number decorated with thick plumage around the sleeves at the 75th Golden Globe Awards in early January 2018. If she wanted to make a statement with both dresses, she certainly did, but perhaps a more subtle take on feathers would look more couture and less costumey.

Angelina Jolie kept in character for the 2014 "Maleficent" premiere, wearing a black, draped, strapless Atelier Versace dress that channeled her dark fairy role. While the shape of the floor-length gown hugged Jolie's figure beautifully, the fabric was reminiscent of a household item. The shiny black material was likely intended to look like leather but instead resembled a garbage bag. Perhaps the "Wanted" star was channeling her goth '90s days, when she was frequently clad in leather, but this time, it looked like something contractors use on a construction site.

InStyle shared the look on Facebook, and fans expressed the same sentiment. "Love her, but that looks like a nicely draped garbage bag," one commented. Another bluntly agreed: "Looks like a trash bag." The good news is that if anyone wants to recreate the look for Halloween, they can just visit their local hardware store for the material.

Angelina Jolie has worn many outfits that caused quite a stir, and her 2000 Academy Awards look was definitely one of them. She's known for her love of black dresses, so it wasn't surprising that she attended the ceremony clad in the color from head to toe. However, her Morticia Addams aesthetic was not at all Oscar-worthy. Jolie showed up in an inky Marc Bouwer gown with long sleeves and a fitted skirt. With her straight, jet-black hair reaching her waist and her face devoid of any color, she looked just like the kooky "Addams Family" character.

Jolie nabbed her first Oscar for best supporting actor for "Girl Interrupted" that year, so at least she had some gold color to add to her 'fit. Equally dressed like a vampire was her brother, who came along as her date. It seemed black was Jolie's lucky color that night, and thankfully, she has since stepped up her fashion game.