Mariah Carey's Most Inappropriate Outfits So Far

Mariah Carey's fashion has come a long way since she broke into the music scene in the early '90s. Back then, her looks were more understated, often involving her casually styling her favorite little black dress with matching stilettos or knee-high boots. Carey had a girl-next-door aura about her, but since becoming a recognized diva, her 'fits have become as big and bold as her high notes. Even when she's dressed in low-key jeans and a tank, the "Emotions" singer is rarely seen in anything but heels, and even during a beach jaunt with her then-boyfriend James Packer in 2015, Carey notoriously wore super-high platform sandals that made our ankles hurt from just looking at her.

Aside from the ill-suited footwear on the sand, Carey has had several other incidents over the years where her wardrobe was completely out of place and inappropriate for the setting. Once "The Emancipation of Mimi" began, the Grammy-award winner's ensembles became riskier, with some head-scratching 'fits that she should have kept at home. From nighties as red-carpet looks to wardrobe malfunctions, Carey's many inappropriate outfits were simply not a "Vision of Love."

Lace slip dresses are the flirtier option for warm days and warmer nights, but Mariah Carey looked like she was wearing a literal nightgown at the 2000 Blockbuster Entertainment Awards. With the satin bodice and rhinestone-studded lace detailing, as well as the very short hemline, Carey should have just shopped at Victoria's Secret for the event and called it a day. The least she could have done was style her look better with some fancy jewelry and a cute cropped cardigan to make it appear as if she didn't just roll out of bed.

The Nickelodeon Kids' Choice Awards is a family-friendly event, which is why Mariah Carey's super-revealing outfit in 2017 was all wrong. While strutting the red carpet with her daughter Monroe, the "Butterfly" singer wore a tight navy-blue athletic-style dress with the zipper opened low on her chest. The short hemline wasn't appropriate either, and an inch higher would have definitely resulted in a wardrobe malfunction. It looked like Carey was twinning with Monroe, who looked adorable in a similar outfit, but perhaps the mom of two should have saved the dress for a more grown-up occasion.

Looking at Mariah Carey's long-sleeved black knit dress, sheer stockings, and knee-high boots, one would think she was seen out and about in London, England, during the fall. However, this cozy 'fit was worn in June 2025, and we don't know how Carey didn't melt under the sun. Perhaps the London weather was a bit cool, as it wasn't yet summer. Still, she could have worn something more seasonally appropriate than her cold-weather attire, like a cute sundress and blazer.

After Mariah Carey's complete weight-loss transformation, we don't blame her for wanting to flaunt her figure. In February 2025, she shared a carousel of pics on Instagram showing off her body in a sheer black sweater and tight pants. Carey completed her all-black look with a pair of high-heeled booties, and while this 'fit would have been fine anywhere else, it was just not appropriate for playing golf. Hopefully, she was just posing for a pretty picture and not actually teeing off, because a rolled ankle is waiting to happen with those shoes.

Sitting in the first row of a basketball game means you're definitely going to get noticed, and Mariah Carey unfortunately turned heads for the wrong reasons at the a 2017 NBA game between the Atlanta Hawks and the Los Angeles Clippers. While wearing a dangerously low-cut shirt, Carey had a near nip-slip, which she seemed unaware of. Unfortunately, the strands of diamonds around the "Fantasy" singer's neck only drew more attention to her chest area, but at least they provided a bit of a distraction from the NSFW moment.

We're no diplomats, but we're sure Mariah Carey broke a few etiquette rules when she showed up to an event honoring the 2016 United Nations secretary-general, Ban Ki-moon. Carey's 'fit consisted of a lacy black bra on full display with a leather jacket zipped down near her ribcage. Not only was the ensemble completely inappropriate in front of a government official, but it was also way too casual, as Carey looked like she was dressed to go bar-hopping with her gal pals. She definitely should have consulted a stylist before getting dressed that day.