Sabrina Carpenter's Worst-Dressed Moments

Sabrina Carpenter has accumulated an incredible following ever since her album "Short N' Sweet" made her a tiny (five feet to be exact), yet huge celebrity. In her new era of fame, Carpenter has brought with her a unique sense of style that has made her an icon. However, the "Taste" singer hasn't always had this chic fashion aesthetic.

Carpenter has been entangled in some of her most controversial moments because of her style — including the time she sported a black tulle mini dress in an esteemed Catholic church — but she has also brought a new wave of trends. Her pastels and babydoll dresses are a modern feminine twist on a retro mid-20th-century style movement. Her short hemlines and frilly skirts are now completely adored by Carpenter's fans and non-fans alike. However, before her music career kicked into overdrive, the former Disney star had a few fashion flops in her day.

The 2017 American Music Awards were met with some interesting red-carpet looks, like Julia Michaels' tulle gown with a weird chest cutout and Alessia Cara's oddly casual track pants. Sabrina Carpenter stepped out on the red carpet that night clad in a plaid jacket dress that immediately put her on E! News' worst-dressed list for not living up to the glamour of the AMAs.

Along with the colorful number — that was closed with two black buttons and looked like something a lumberjack's wife would don — Carpenter wore nude, knee-high boots, chunky gold earrings, and her hair in a half-up-half-down 'do. The material of the dress certainly didn't help her cause, since it looked like it was made out of a fabric normally set aside for household robes. However, the "Please Please Please" hitmaker's sense of humor completely redeemed her failed outfit. Carpenter revealed to the AMAs in an interview that her feet were feeling the height of her heels, but joked that she could still totally run a marathon in them.

One of Sabrina Carpenter's staple style choices as a budding musician in the mid-2010s was casual red carpet looks. She stuck with that go-to fashion faux pas of hers backstage at Atlanta's Power 96.1 radio Jingle Ball in December 2018. Carpenter wore a simple oversized, bright orange t-shirt, which fit like a dress on the pint-sized singer. Some of her other red carpet moments consisted of the same look, with an oversized tee or sweatshirt paired with a boot. 

The MSGM shirt, emblazoned with a vintage photo of dancers doing the Charleston, is so neon orange that it washes out Carpenter's fair skin. Her knee-high black leather boots accentuate the chaos, making her outfit look more like a Halloween costume than one to ring in the holidays at a Jingle Ball concert. While on any other occasion, the smoky eye would look fantastic on Carpenter — as she is one of the many Disney stars who look unrecognizable without their makeup — the black eye shadow just seems too intense for a night of holiday cheer.

Listen ... Sabrina Carpenter's look at the 2017 Harper's Bazaar Celebration of Icons by Carine Roitfeld was the beginning of her style transformation from grunge to girly, but there are a few aspects of the look that night that just don't fit. The "Girl Meets World" actor donned a stunning lavender-purple Cinq à Sept dress with strappy black heels (per Elle Magazine). Other than the fact that the dress's off-the-shoulder sleeves and stringy bow were a little distracting, the outfit is adorable. However, setting aside the out-of-place chunky gold jewelry, Carpenter boldly paired the look with black lipstick.

The dark lip transformed the outfit's vibe from cute, spring-day chic to something Carpenter would wear if she was still on The Disney Channel and had to play a witch. Plus, while this would have otherwise been such a flattering color scheme with her skin tone, the black lipstick totally washes her out. The whole look was uncoordinated, which made each element seem like it was just plucked from her bedroom as she rushed out the door.

Sabrina Carpenter attended her first MTV Video Music Awards in 2018 after releasing her third album, "EVOLution," two years before. The singer's classy, all-white look was elegant, but a little haunting. Her shiny, pearl-colored gown incorporated some extra fabric that was tied around her neck and draped down her arm in the form of a sleeve, making the dress look more like a mummy costume.

With all the excess material, including the train at the bottom of the dress, the outfit looked heavy on Carpenter, with the leg slit desperately attempting to balance the bulkiness of the dress' bodice. However, the color of the dress was complimentary against her skin tone, and she knew it. That's why the star wore white again at the 2024 VMAs, this time walking the red carpet in a timeless, Marilyn Monroe-esque sequin gown, which perfectly hugged her body. Carpenter has grown into her style since the 2018 VMAs, now frequently donning vintage-inspired looks that match her voluminous blonde blowouts and big blue eyes; a modern Golden Age princess.

While it might be controversial to say, Sabrina Carpenter's "Sleeping Beauty" look at the 2024 Met Gala was a little too sleepy. For someone who is normally clad in the most shimmery, bold fashion, Carpenter's gala gown was fairly simple. The black body-con dress wasn't anything to write home about, and the giant blue bubble skirt just made the "Espresso" hitmaker look like a cloud (maybe it's an homage to her weather-inspired song "Tornado Warnings").

After the Met Gala, which Carpenter attended with her boyfriend Barry Keoghan, many fans were quick to comment on her outfit that night, calling it basic. "My girl i'm streaming espresso every day but this i cant defend it, this is straight up boring for a met look," one X (formerly Twitter) user wrote. Others thought the musician was absolutely stunning, with one commenter on Carpenter's Instagram calling her a "beautiful blue flower princess."