Taylor Momsen's Most Inappropriate Outfits So Far

Fans of Taylor Momsen may recognize her as a child star who grew up to be gorgeous, and Cindy Lou Who from "How the Grinch Stole Christmas" is unrecognizable now. No longer the cherubic little girl, the Pretty Reckless singer has traded her polka dot dresses for lace and leather. Taylor Momsen's stunning style transformation over the years included colorful Y2K 'fits from her "Gossip Girl" days, but her true fashion tastes were quickly revealed to be more on the grunge side. In 2009, she told Teen Vogue, "I have a lot of favorite items, but one favorite staple that I could never get rid of is my black leather jacket. It's perfectly worn in. And keep in mind that I have a lot of leather jackets, but there's just that one I always want to put on."

While you can never go wrong with a classic staple, Momsen often pushes the envelope with her fashion, sometimes to the point of her outfits being completely inappropriate. Since becoming a rock star, the "Make Me Wanna Die" singer has adopted a super-edgy look, which is totally on brand. We love it when celebs express themselves through their clothes, but sadly, Momsen has missed the mark way too many times.

Spotted: Taylor Momsen at the Rock & Roll Hall of Fame induction ceremony in November 2025, wearing a completely sheer black dress without a bra. We all know that leather and lace are a rock star's uniform, and Momsen made sure to choose the latter for the event, with her chest on full display. At least she covered up her lower half with a pair of nude panties, but the former actor looked practically naked underneath her peekaboo gown. If she wanted folks to take notice, we're sure she had everyone doing a double take.

The MTV Video Music Awards is the time to have fun with fashion, with many celebs wearing super avant-garde outfits in 2025. However, Taylor Momsen's 'fit was a total bore, with the singer-songwriter wearing a plain black bralette and a low-slung leather maxi skirt. We would have loved to see her bra top adorned with rhinestones, but it just looked like your basic cotton lingerie, making the whole look inadequate for the event. The only interesting thing about Momsen's look was her amazingly toned abs.

Taylor Momsen loves a barely there look, which she proved at the KidSuper Funny Business Comedy Fashion Show in September 2024. The "Miss Nothing" singer showed up at the event wearing a graphic black-and-gray button-up shirt that was completely open, revealing black pasties covering her nipples. Although it was likely intentional, this inappropriate look made it seem as if Momsen had experienced a wardrobe malfunction on the way to the event and decided to just go with it. We just hope she wasn't chilly while posing in the fall weather.

Wearing lingerie as clothing was big in 2010, but instead of incorporating a piece into her outfit, Taylor Momsen looked fit for a boudoir photo shoot. While promoting the launch of John Galliano's perfume that year, the "Underdog" actor wore a studded bustier complete with garters and thigh-high stockings. Adding to Momsen's pin-up girl look was a furry black coat and extra-high platform sandals. What's more, it looked like she had a tear in one stocking. While the designer was dressed in his usual quirky outfit, the two looked like a mismatched mess.

Taylor Momsen was barely a teen when she first started filming "Gossip Girl" in 2007, so we get why she would veer towards a bright-pink dress for the show's premiere party. However, the strapless top and puffy skirt were reminiscent of a tacky 1980s prom dress from the discount rack. Momsen looked painfully overdressed, especially next to Blake Lively in a plain shirt and pants. Meanwhile, Leighton Meester looked more sophisticated in a sheath and strappy sandals. We're sure this is one 'fit Momsen is looking back and cringing over, especially since going goth.

A year after her "Gossip Girl" debut, Taylor Momsen's style became more experimental. Case in point: the ill-fitting "poncho" dress that she wore to New York Fashion Week in 2008. The off-the-shoulder style draped over Momsen's body looked two sizes too large, with the front bunched up in an unflattering way. Adding to her sloppy look was a pair of tight leather pants, and it's clear even Momsen wasn't immune to the mid-aughts skirt over pants trend. At any old party, this would have been a bad look, but it's a downright crime at fashion week.