Jennifer Aniston has long been known for her girl-next-door look, thanks to her adorable, relatable, and friendly demeanor. And while she’s quite different from vampy, sultry A-listers like Angelina Jolie, she’s worn some scandalously inappropriate outfits over the years. While she consistently shows up in magazines for her red carpet looks, they’re not always in her favor. Here are the most inappropriate Jennifer Aniston outfits of all time.
Her Bold ’90s Fashion Moment That Still Turns Heads
By the late 1990s, Jennifer Aniston was no longer just everyone’s favorite sitcom star — she was fast becoming a global style icon. Her rise to fame in the late ’90s came with a major boost in confidence—and her 1999 SAG Awards look proved it. Ditching the safe red-carpet formula, she arrived in a daring black ensemble that instantly turned heads. The outfit paired a flowing pleated skirt with a bold, upside-down bandana top that showed off her famously toned abs and glowing shoulders. It was sleek, unexpected, and far removed from the polished style of Rachel Green, her Friends alter ego.
The ultra-low waistline of her skirt pushed boundaries, perfectly capturing the rebellious spirit of the decade. While The Matrix was inspiring a wave of black leather fashion moments, Aniston took the trend in her own direction—minimal, effortless, and unapologetically sexy. The look became one of her most talked-about fashion risks, signaling that Hollywood’s sweetheart wasn’t afraid to surprise. Decades later, it remains a defining ’90s style moment that still feels bold, fresh, and unforgettable.
Elle’s 18th Annual Women in Hollywood Tribute
At this event in October 2011, Jen showed off her legs and her cleavage in a sparkly, silver Kaufmanfranco with a plunging neckline. She wasn’t afraid to show off some skin in this look with her plus-one and future ex, Justin Theroux. Aniston was one of the women honored at the event. Despite being recognized for her acting skills at the event, the media continued to remain obsessed with her reproductive decisions, love life, and whether she would ever have a baby.
A barely-there mini-dress for the “Life of Crime” premiere
At the Life of Crime premiere in 2014, Aniston wore a slinky, ultra-short Saint Laurent dress that skimmed the top of her thighs and a super low-cut top that barely covered her breasts. To cover up the provocative look, she wore a cropped black blazer. This look was in the tabloids for paparazzi, assuming she was rocking a slight baby bump, which she had to refute in an op-ed for HuffPost, where she explained how fed up she was with body shaming in Hollywood.
A suit with a blazer, but no shirt, at the Critics’ Choice Award
Is there anything more girl boss than rocking a well-tailored suit without a shirt underneath? At the 2015 Critics’ Choice Award, she showed up in a smoldering red suit selected from Dolce & Gabbana’s spring 2015 collection. The only accessory she wore with it was a chic gold body chain. Even for Aniston, who often bares her chest at public events, this was a bold look. She also brought Justin Theroux to this event, and they wed seven months later.
A risqué look at the 2017 Oscars
Aniston was giving Hollywood siren at the 2017 Oscars, where she wore a navel-plunging gown with a thigh-high split. The sparkling black dress was paired with approximately $13 million worth of Lorraine Schwartz diamonds, which included stunning 100-carat diamonds in emerald-cut earrings. Some were surprised by how blinged out Aniston was, since she told a NYT reporter in 2015 that she’s “not a diamond girl.”
Her sparkling, skin-baring Versace minidress at the 2023 Murder Mystery 2 premiere
Jennifer Aniston has spent decades proving she’s not afraid to surprise—and her 2023 Murder Mystery 2 premiere look was proof she’s still got that fearless spark. Skipping the “good girl” image entirely, she stepped onto the red carpet in a shimmering, semi-sheer metallic Versace minidress that seemed to glow under the lights. The silver mesh and delicate strips revealed just enough skin to turn heads without crossing the line, creating the illusion of a dress that showed more than it actually did.
The moment was pure Jennifer—elegant, confident, and effortlessly daring. While her look stole the show, she playfully poked fun at her co-star Adam Sandler, who arrived in a baggy New York Knicks sweatshirt, the perfect comic contrast to her high-fashion statement.
For Aniston, fashion has always been about freedom, not fitting into anyone’s box. As she once said, “Don’t let yourself become comfortable and play it safe.” Decades into her career, she continues to prove that advice true—still bold, still evolving, and still the woman who can make a red carpet light up.