Sabrina Carpenter Outfits That Missed The Mark

Sabrina Carpenter has created several iconic looks over the years, marketing herself as a fashion icon. An integral aspect of her "Short n' Sweet" tour revolves around her revealing the different colors and patterns of her signature outfits each night. On the red carpet, we can expect to see her re-vamp and reference legendary Hollywood icons; such was the case with her 2024 VMAs look, where she channeled Marilyn Monroe in "Gentlemen Prefer Blondes," in a breathtaking Bob Mackie silver beaded gown that Madonna wore back in the '90s.

That being said, it's crucial to look back on Sabrina Carpenter's stunning style transformation, because her looks weren't always as legendary as they are currently. Having first signed with Disney Music Group's Hollywood Records when she was 12 years old and landing a starring role in Disney Channel's "Girl Meets World" in 2013, Carpenter has seen her fair share of paparazzi and red carpets. We all remember the styling of Disney Channel's past, marked by lots of layers, patterns, colors, and accessories, and Carpenter's experience was no different. Though they are few and far between, let's examine some of Sabrina Carpenter's looks that missed the mark.

Everyone has an embarrassing outfit they wish they could forget. Sabrina Carpenter's was documented by photographers and will live on the internet forever — yikes! In 2011, she attended her first red-carpet premiere for the "Kids Helping Kids: Japan" music video and decided to wear a gray T-shirt with matching arm warmers, a black jacket, skirt, and patterned tights. She finished off the look with black ballet flats and a matching headband. If it doesn't already sound bad, Carpenter confirmed her regret to W Magazine in November 2024: "Bad ... just when you think it can't get worse, like, the accessories had to come in ..."

Sabrina Carpenter's look for the June 2016 premiere of her film "Adventures in Babysitting" was another miss. The "Espresso" songstress donned a gold Prada dress that pulled our eyes to all the wrong places. For starters, the bateau neckline is so stretched that it falls off one of her shoulders, and the elbow-length T-shirt sleeves are just plain unflattering. In terms of the silhouette, the belt at her waist hardly cinches in the wrinkled, ill-fitting garment. She kept the accessories minimal, wearing an embellished gold character shoe as her footwear. Yeah, we're gonna have to pass on this one.

Sabrina Carpenter has been known to dress for revenge, but her outfit for the 2017 American Music Awards was lackluster. The singer-songwriter opted for a Missoni trenchcoat-style garment as the centerpiece of the look, going sans shirt. The multi-colored tartan robe looked plain and lifeless, aging Carpenter in the process. She attempted to spice up the look with a pair of beige thigh-high platform boots, but the floor-length coat just didn't blend cohesively with the proportions of the boots. Standing at 5 feet tall, it's probably best that Carpenter avoid lengthy coats moving forward. We aren't sure if this is a red-carpet outfit the star regrets, but it's certainly worlds away from her current style aesthetic. 

Sabrina Carpenter was barely on the brink of adulthood when she attended the 2017 Billboard Women in Music event, but her Céline gown aged her a few decades. The bubblegum-pink garment consisted of a simple yet elegant floor-length bubble hem and an attached cape. She finished off the look with some nude kitten heels, but kept her nails painted black for a youthful, albeit misplaced, touch. The look was sophisticated and high-class, which felt a bit conflicting when compared to Carpenter's trendy and current vibe. This was another minimally accessorized look, so even a simple bracelet or watch would have made a statement that changed the whole vibe.

It took several years for Sabrina Carpenter to curate the perfect performance looks, and the proof is in the pudding. She brought the glitz and glam to the 2018 Jingle Ball, literally. The "Please, Please, Please" singer graced the stage and the red carpet in a Moschino jumpsuit that was embellished in silver from top to bottom. Attached was an awkward, satin draping bustier, which she paired with some black platform pumps. As a whole, the mismatched textures and sheer brightness of the outfit made Carpenter stick out like a sore thumb, but at least she put the "jingle" in Jingle Ball.