Most Inappropriate Jennifer Aniston Outfits Of All Time

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.