5 Sabrina Carpenter Outfits That Totally Missed The Mark

When it comes to fashion icons, there's no denying that Sabrina Carpenter is the new 'It girl,' as she's often seen wearing the most stylish outfit on every red carpet she walks. The singer has us begging "Please Please Please" for hot new looks almost every day, and we love her dedication to fashion risks (that retro red and white striped outfit for Vogue World 2024, anyone?) But every risqué outfit isn't guaranteed to pay off, and Carpenter — like many other celebrities — has learned that the hard way.

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Not that she cares, though. Carpenter's bold and sparkly stage outfit choices have raised so many eyebrows that she spoke about it in a October 2024 Time interview. "You'll still get the occasional mother that has a strong opinion on how you should be dressing. And to that I just say, don't come to the show and that's OK," she said. And we love that attitude. But while most of her outfits have been knockouts (despite what some moms say), a few have totally missed the mark.

Her red carpet debut was a let down

Sabrina Carpenter made her red carpet debut in 2011 at 11 years old for the launch of the "Kids Helping Kids: Japan" music video. We're all for youngsters experimenting with fashion to find their style, but the rhinestone armbands and lace-effect hosiery were too busy to wear together. We'd have liked more color from the pre-teen too, as the gray and black aged her. Carpenter agreed this wasn't her best, telling W in September 2024, "[It was] an ugly skirt, and ugly jacket, an ugly top, and ugly headband. Just when you think it can't get worse, the accessories had to come in."

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Her oversized mustard hoodie was a missed opportunity

We've seen Sabrina Carpenter wear some stunning red carpet gowns over the years, so we felt disappointed when she attended the iHeartRadio Jingle Ball in 2018 in something that was the complete opposite from the glam we'd witnessed. Carpenter wore an oversized, bright mustard hoodie without any pants (she was years ahead of the pantsless trend), and chunky, flat black combat boots. Although she certainly looked cozy, the hooded dress totally swamped her 5-foot figure. Notably, the ill-fitting sleeves bunched around her wrists, making the piece impractical and bulky. The addition of something as simple as a black waist belt would have made it edgier and put together. However, the look overall was a missed opportunity for the rising star to wear something more glamorous.

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She wore black lipstick with a purple dress, but it didn't feel authentic

The "Nonsense" singer loves her retro trends and girlie ensembles with sparkles, but her 2017 Harper's Bazaar Celebration of Icons by Carine Roitfeld style felt inauthentic. The gown, accessories, shoes, and makeup all seemed like they were plucked from different wardrobes and vanities, with nothing really coming together.

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On top of that, the light purple leaf dress washed Carpenter out and looked totally drab, while the dark lipstick did nothing to warm her skin. Strappy black heels are a neutral staple but in this case, metallic footwear would have been a chicer choice. Swapping her vintage-looking, chunky gold jewelry for simpler pieces would also have modernized the outfit.

Sabrina Carpenter's gold Radio Disney Music Awards dress was too big and unflattering

Sabrina Carpenter attended the "Adventures In Babysitting" premiere in 2016 in a wide neck, gold dress with drop sleeves and a matching waist tie. Though the belt cinched her waist, the oversized dress was too baggy and ceased awkwardly. That meant the excess material hung around her torso and off her arms in an unflattering way. The get-up also didn't work because her feet didn't fit into her gold heels, causing her toes to spill over the side, which was surely uncomfortable. One thing we will give the "Taste" singer props for, though? Her chic black nails, which can be an adult manicure staple.

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Her silver and blue Radio Disney Music Awards dress was too busy

Sabrina Carpenter wore a white and navy dress to the 2016 Radio Disney Music Awards that was far too busy. It had multiple stars on the left side of the neckline and an odd empire-waist lace that hung from her mid-torso, which added unwanted bulk over her hips. It also featured distracting large sequins on embellished strings over her thighs, while the awkwardly frayed bottom appeared unkept as it blew in the breeze. Individually, each section could have worked, but they had no correlation and overwhelmed the star's small frame.

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