Nothing did more to solidify Jennifer Aniston’s image as a squeaky-clean good girl than her iconic portrayal of Rachel on “Friends.” However, what people may not remember, or realize, is that while Aniston does seem like a delightful celebrity, Rachel was just a role, and Aniston has often taken to the red carpet to wear an outfit that feels out of character because of the supposed “good girl” persona. In fact, she’s hinted at the many ways in which she is not Rachel, including revealing to Glamour that she was not a fan of the much-desired Rachel bob haircut, even calling it “cringey” to her.

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Of course, Aniston is one of Hollywood’s legendary beauties, with a seemingly ageless body that has brought her to red carpets for other successful shows and films such as “The Morning Show,” a movie actually titled “The Good Girl,” and “The Break-Up,” which debuted her much talked about nude backside and at the time certainly signaled that Aniston was not afraid to push back on her good-girl image. In real life, Aniston has found plenty of opportunities to show off her wilder side in several outfits that would certainly have some pearl-clutchers thinking twice about bringing her home to meet their parents. 

As Jennifer Aniston’s fame grew (along with her net worth), she also grew more confident in her outfits. And in 1999 she hit the red carpet for the SAG Awards wearing a very hip combination of a long, pleated black skirt and a black, upside-down bandana-style top. She showed off her legendary toned abs and bare shoulders with a look that was as shockingly cool as it was drastically different from something Rachel from “Friends” would wear. Let’s not forget about the jaw-droppingly low waist of her skirt, a revealing look that screamed the ’90s but may have been a surprising choice for a red-carpet event.

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The trendy outfit coincided with the end of the ’90s as “The Matrix” ushered in an era of leathery, black looks (just look at her “Friends” co-star Courtney Cox’s outfit), and Aniston’s on-trend tube top would become a look that filtered through fashion, creating a memorable outfit that also did plenty to dispel the idea that Aniston was simply a good girl who never took any fashion risks.

It might look like Jennifer Anniston was fully clothed for her 2003 People’s Choice Award appearance, but there are plenty of photographs to suggest that she was one hug away from a wardrobe malfunction with her open-shirted, no-bra outfit. The outfit was a delightful twist on a simple look given that Aniston had broken her toe and was walking with a cane while her other foot was in a boot. While it’s certainly not the biggest controversy to which Aniston has been tied, Aniston flirted with offending public decency with her plunging open shirt topped with a diamond-laced choker that seemed designed to remind onlookers and photographers to keep their eyes focused on her chest-baring look — and not the garish plastic boot around her foot.

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Aniston would go on to win the award for Favorite Female Television Performer for “Friends,” beating out Patricia Heaton of “Everyone Loves Raymond” and Deborah Messing of “Will & Grace.” She took to the stage with her cane, boot, and open shirt to accept the award to screams of adoring fans. Afterward, plenty of photos were taken of Aniston with her award that suggested while she may have been known for her good girl persona, she wasn’t afraid to risk a slip-up to make sure that every outfit was memorable — no matter the circumstance.

Jennifer Aniston upgraded her chest-baring look in 2011 when she was chosen for Elle’s 18th annual Women in Hollywood tribute, where she combined peaking cleavage with a minidress hem that showed off her killer legs. Aniston was photographed in a Kaufmanfranco metallic mini dress that she paired with Balenciaga heels while carrying a Salvatore Ferragamo clutch. In speaking to Elle about her experiences in Hollywood, Aniston offered a story about truly inappropriate behavior when she told the outlet that she once threw a chair at a director, saying, “It wasn’t my proudest moment. He was treating a script supervisor horribly … When the director walked in, I threw a chair at him. I missed, of course. I was like, ‘You can’t speak to people like that.’ I can’t tolerate it.” (via The Hollywood Reporter) We love to see a morally sound icon.

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And according to PageSix, plenty of people took note of the assets that Aniston had been revealing on the red carpet. At the time, a poll conducted by Yahoo! and Fitness magazine surveyed 2,000 people and came back with the opinion that 34% of women wished they had Aniston’s body and 31% of men wished that their partner had her body. That being said, we’d like to remind everyone that Aniston has politely dodged any and all plastic surgery rumors. It all goes to show that while Aniston may have a reputation for being a good girl, whether inappropriate or not, everyone wished they were her or wished they could be with her. 

Jennifer Aniston on the December cover of Allure Magazine.

Photographed by Zoey Grossman. pic.twitter.com/T26QFxu3j9

— IAMFASHION (@IAMFASHlON) November 9, 2022

There is no doubt that Jennifer Aniston knew she would be pushing some buttons when she debuted a truly bare-it-all look for Allure in 2022. The then 53-year-old decided to pose for a series of revealing photographs; in one, she was wearing a teeny-tiny Chanel bikini top that looked like bottle caps. Other photographs also pushed boundaries, with one memorable image of the beautifully aging actor covering her topless self while a Gucci G-string rode out of her pants. Not everyone was thrilled with the look, with one user on X, formerly known as Twitter, flatly saying, “Not flattering at all.” Aniston had by then transitioned from a “good girl” to a “good older woman” persona — and after getting past plenty of unwanted and hard-to-ignore rumors about her, including whether she would ever be a mother,  the outfit feels like a polite kiss-off to the far more inappropriate probing into whether or not any given photo of her ever revealed a “baby bump.”

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As for what Aniston thought of the revealing looks, she told Allure, “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 … You’re going to be 65 one day and think, I looked f***ing great at 53.” Fans seem to agree, with one user on X saying that the outfit was “the coolest she ever looked.”

With plenty of opportunities to stick it to her good girl image, the actress has shown no signs of slipping into a fashion comfort zone. Take for example her 2023 semi-see-through metallic Versace minidress that she wore to the premiere of “Murder Mystery 2.” The strips and mesh of silver were dappled with portions that showed off her skin beneath, offering a look that appeared to reveal more than it did. While it may have been a little more revealing than an outdoor public premiere called for, Aniston was more (jokingly) upset by her costar Adam Sandler going in the opposite direction and wearing a bulky New York Knicks sweatshirt to the photo op.

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So while Aniston may genuinely be a good girl, she has made plenty of fashion decisions that show that she is not afraid to turn heads and get a couple good gasps out of those who think she looks better always looking like Rachel. When speaking to ScreenSlam in an interview for “The Good Girl,” Aniston talked about how the role helped her take chances again, with her response feeling like a larger examination of the labels attached to her. “You can feel stuck. And not only do you feel stuck, but the world sort of sticks you somewhere, and they put you in a little box, and in a category,” she said, adding she learned to break free from that mentality. “Don’t let yourself become comfortable and play it safe. Because you’ll burn out. And I want to do this for a while. I want to be around for a little while longer.” Many years later she certainly has, and we can’t wait to see what outfit she turns our heads with next.

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