8 Jennifer Aniston Outfits That Totally Missed The Mark

Fans have been coveting Jennifer Aniston's cool-girl style for decades, and for good reason. The "Friends" star is known for wearing elevated basics during her downtime and switching her 'fits to the most elegant, classic gowns for the red carpet. Over the years, Aniston has worn some timeless outfits that are practically begging to be recreated , and while she doesn't go for super avant-garde looks, you could regularly rely on her to slay black tie events. Unfortunately, even the A-lister doesn't always get it right, and she's had some sartorial misses that will go down in fashion history.

Aniston's style is pretty formulaic: body-hugging sheaths, LBDs, and column gowns for more formal occasions. However, when she strays from her usual looks, that's where things tend to go wrong. There's no denying that the "Murder Mystery" actor has been on the best-dressed list countless times, but throughout her career, she has stepped out in several outfits that just didn't work.

There are times when celebrity LBDs prove the iconic outfit's versatility, but Jennifer Aniston failed to have a moment with hers in September. While visiting "The Late Show with Stephen Colbert, Aniston was seen in a baggy black frock with a mock turtleneck and a belt perched curiously below her hips. With the matte fabric and the gold buckle, Aniston looked like she was wearing a witch's hat from Party City. The loose fit also did nothing to highlight her figure, but she totally gets bonus points for showing off her super-toned arms.

We rarely see Jennifer Aniston in patterns, which is why it was surprising to see her in florals at the "We're the Millers" premiere in 2013. Although promotional events are a time to have fun with fashion, Aniston's dress did not exude the sophistication that she's known for. In fact, it looked like a kid's Easter dress, complete with a double-layered skirt and a dizzying array of small flowers scattered throughout. Add in some messy, tousled waves, and Aniston's playground look was complete.

Jennifer Aniston experimented with different fashion looks during her earlier career days, as was apparent when she arrived at the 1999 Emmys in a gaudy paisley-patterned dress. The usually simple-attired actor was bejeweled to high heaven with rhinestones all over her torso, while the burgundy skirt remained bare and fell to the floor in a clumpy mess. Aniston accessorized with a stack of gold bangles and a tiny purse, with her hair in beachy twists. We get that she likely wanted to match her then-partner Brad Pitt's surfer aesthetic, but the whole boho-chic look did not work for her.

The Women in Film Honors is an annual event that celebrates females in the movie industry. While the dress code isn't as formal as the Oscars or Emmys, attendees are still expected to show up in fierce 'fits, which is where Jennifer Aniston dropped the ball in 2009. The shiny silver cocktail dress looked like crinkled foil, and there was an odd bunching happening around the waist. We're not sure if the material was meant to look rumpled, but the overall effect was unflattering. Additionally, strapless metallic dresses are so '80s, and this is one outdated trend Aniston was caught wearing that should have been left in the past.

Was Jennifer Aniston headed to a frat party after the 2010 premiere of "The Bounty Hunter?" Because she sure looked like it with her toga-styled beige dress that resembled a large bedsheet thrown haphazardly over her frame. The warm color complemented Aniston's skin tone perfectly, but the unadorned fabric was way too plain for the red carpet. We know that Aniston is an actual Grecian goddess, so we wish she had gone for a more regal gown than that shapeless frock.

Back when pop stars made dresses over pants a thing in the early 2000s, it seems Jennifer Aniston allowed herself to get sucked up in this trend. While joining her "Friends" cast for an NBC anniversary celebration in 2002, the Rachel portrayer donned a sheer black floral dress with an asymmetrical hemline over a pair of slim-fitting black pants. Thankfully, Aniston refrained from wearing flared jeans with the dress, or else her Y2K 'fit would have looked even more dated.

Back in the early 2000s, many stars didn't get as glammed up for movie premieres as they do now, but even with a casual dress code, Jennifer Aniston's outfit for "The Mexican" showing was a total snooze-fest. From the plain V-neck sweater to the frumpy white jacket and pants combo, the "Wanderlust" star looked like she was headed to a corporate shindig. Combined with the chunky white sandals and simple handbag, Aniston had the air of a manager awkwardly perusing the room for a familiar face. Surely, she could have stepped it up for her then-husband, Brad Pitt's big night.

Jennifer Aniston has worn a lot of leggy looks over the years, with her 2016 Critics' Choice Awards gown being one we won't forget. While the dress' bluish-gray hue and soft chiffon fabric were dreamy, the slit going up the middle of the skirt looked like a wardrobe malfunction waiting to happen. In fact, it seemed Aniston was all too aware of a possible peekaboo moment, as she had an uncomfortable expression on her face and made sure her legs were crossed while posing for photos. Perhaps next time, she'll go for a side slit instead.