Inappropriate Outfits We Can't Believe Jennifer Aniston Wore

Jennifer Aniston is everyone's favorite girl next door — if you lived next door to an über-fit A-list celebrity. She's seen as cutesy, relatable, and, well, nice. The antithesis of the supposedly super sexy and vampy Angelina Jolie. However, Aniston isn't all yoga pants and salads; she's rocked more than her fair share of inappropriate outfits over the years.

Whenever Aniston is on the red carpet, she makes it into the glossy mags. However, it's not always on the best-dressed list, and even Aniston has made fun of some of her fashion choices — including at the "Friends" reunion. She took to Instagram Stories in June 2021 (via People) to poke fun at the Rachel Green-style sleeveless mock turtleneck she wore for the HBO special.

Rachel has shadowed Aniston throughout her career thanks to her iconic bob that became the look of the 1990s. It was so popular that Entertainment Weekly declared it the most desired hairstyle of the Clinton era and one of pop culture's most influential looks. However, Aniston wasn't a fan of the famous "Friends" haircut. "How do I say this? I think it was the ugliest haircut I've ever seen," she told Allure in 2011. Aniston's also not a fan of Green's wardrobe choices, which mainly consist of boyfriend jeans, denim vests, and lots of cardigans. Instead, she prefers stylish and classic A-line silhouettes, tailoring, and neutral tones. However, she likes to mix it up occasionally and walk on the wild side. We're checking out some inappropriate outfits we can't believe Aniston wore.

Aniston's leg-flashing, cleavage-baring Women in Hollywood look

Jennifer Aniston's got legs and she knows how to show them. The celeb's lower limbs were on full display — along with her décolletage revealing cleavage — at Elle's 18th Annual Women in Hollywood Tribute in October 2011. Aniston went full-out va-va-voom in a plunging, sparkly silver Kaufmanfranco minidress, Balenciaga sandals, and a Salvatore Ferragamo clutch. Aniston's outfit was totally inappropriate for a trip home to visit Grandma but totally slay for a walk on the red carpet. Her plus one for the night was her then-boyfriend and future ex-husband, Justin Theroux.

Aniston was among nine female A-listers honored at the event, which also included Barbra Streisand, Freida Pinto, Evan Rachel Wood, Naomi Watts, Michelle Pfeiffer, Viola Davis, Stacey Snider, and Elizabeth Olsen.

Even though Aniston was being recognized for her acting prowess, the constant obsession with her love life, reproductive choices, and whether she would ever have a baby inevitably raised its head. "There's no desperation. If it's meant to be, it's meant to be. I'm at peace with whatever the plan is," she told Elle. "But will you hate me if I say I don't want to talk about my relationship?"

Aniston's thigh-skimming, chest-flashing 'Life of Crime' mini-dress

Jennifer Aniston's legs were back on display at the premiere of her black comedy lawbreaker flick "Life of Crime" in August 2014. Her super short and slinky silver Saint Laurent dress skimmed thighs, but the top half raised eyebrows. The dress was so low-cut that it barely covered her breasts. Luckily, she wore a black cropped blazer by the same designer to maintain her dignity.

Still, it wasn't Aniston's inappropriate outfit that hogged the headlines. Instead, what she was supposedly covering up became fodder for the ever-churning pregnancy rumor mill. Aniston's stomach didn't appear as toned and taut as usual, sending the tabloids into a feeding frenzy. Brad Pitt and Angelina Jolie had gotten married just two weeks before the premiere, so speculation abounded that Aniston was sporting a revenge baby bump — because that's a thing, presumably. "The actress showed off what appears to be a slight baby bump. Could a baby announcement be on the way so soon after Brad Pitt, 50, and Angelina Jolie, 39, finally tied the knot?" Hollywood Life demanded to know.

Aniston took her time to answer. "For the record, I am not pregnant," she wrote in a July 2016 Huff Post op-ed. "What I am is fed up. I'm fed up with the sport-like scrutiny and body shaming that occurs daily under the guise of 'journalism,' the 'First Amendment,' and 'celebrity news.'"

Aniston's topless Critics' Choice Awards ensemble

Jennifer Aniston was noticeably absent from the Oscar nominations when they were announced on the morning of January 15, 2015. However, when she walked the red carpet at the Critics' Choice Awards later in the day, she made sure she would never be forgotten. Aniston set temperatures soaring in a gorgeous red suit from Dolce & Gabbana's spring 2015 collection, which she paired with nothing but a gold body chain. Even by Aniston's usual chest-baring standards, it was a bold move.

However, the actor did accessorize with Justin Theroux, whom she married seven months later. The couple first met in 2007 when Aniston dropped in on the "Tropic Thunder" set. They reconnected while filming "Wanderlust" in 2010 and moved in together a year later. They married in a secret ceremony at their Bel Air home in August 2015. Sadly, it was over after just two-and-a-half years.

Not surprisingly, tabloid rumors abounded, with claims that their lifestyles were incompatible and that neither was willing to relocate to the other's home city — Aniston was based in LA, while Theroux was in New York. He shot down the reports in an interview with Esquire in April 2021. "That's a narrative that is not true, for the most part," he insisted. "People create narratives that make themselves feel better or simplify things for them. That whole 'This person likes rock 'n' roll, that person likes jazz. Of course!' That's just not the case. It's an oversimplification."

Aniston's navel-plunging, thigh-high split Oscars gown

Jennifer Aniston looked every inch the Hollywood siren at the 2017 Oscars. She wore a shimmering sequined black Atelier Versace dress with a neckline that plunged down to her navel and a thigh-flashing side split cut to her hip. In case she wasn't sparkling enough already, Aniston accessorized with an estimated $13 million worth of Lorraine Schwartz diamonds, including a pair of 100-carat diamond emerald cut earrings.

It was a surprising look, given that Aniston previously claimed not to be a sparkler kind of chick. "It's a rock, I know. He rocked it up. It took me a while to get used to it," she told a New York Times reporter in January 2015 when they commented on her massive engagement ring from Justin Theroux. "I'm not a diamond girl," Aniston continued. "I'm more Indian jewelry and stuff."

Aniston opened up about her favorite red carpet look in an interview with the Wall Street Journal in August 2023. She said her number one gown was the black one-shoulder Valentino dress she wore to the 67th Annual Golden Globe Awards in January 2010. Aniston said she loved it so much that when she lost the dress — which would seem quite a feat — Valentino made her a replacement copy.

Aniston's barely-there Chanel bikini

Jennifer Aniston threw caution to the wind and dared to bare pretty much everything in December 2022. The actor graced the cover of Allure magazine in a Chanel spring 1996 bikini top that put the I in itsy-bitsy. It's safe to say that the swimwear would definitely be inappropriate for anything swim-related. But who cares? Aniston looked A-mazing.

In the accompanying interview, she opened up about how she's learned to love herself and the skin she's in. "I feel the best in who I am today, better than I ever did in my 20s or 30s even, or my mid-40s. We needed to stop saying bad s*** to ourselves," Aniston said. "You're going to be 65 one day and think, I looked f***ing great at 53."

Aniston turned 55 in February 2024, meaning there was finally an end to the baby bump rumors. After years of, understandably, refusing to discuss her reproduction choices, she made a heartbreaking confession. "I was trying to get pregnant. It was a challenging road for me, the baby-making road," Aniston said of her late 30s and 40s. "All the years and years and years of speculation ... It was really hard. I was going through IVF, drinking Chinese teas, you name it. I was throwing everything at it. I would've given anything if someone had said to me, 'Freeze your eggs. Do yourself a favor.' You just don't think it. So here I am today. The ship has sailed."