Inappropriate Outfits We Can't Believe Sabrina Carpenter Wore

Sabrina Carpenter has said that her diminutive frame is to blame for making it difficult for her to find a style that suits her, but being tiny is no excuse for some of her inappropriate fashion choices. "I [take risks] in a lot of other areas, but fashion was always something that was harder for me because I am very petite," Carpenter told Glamour in 2018. "Things fit differently on me than they do on supermodels." Perhaps this helps explain why she's really leaned into the Bratz aesthetic — instead of dressing like she's ready to strut down a runway, she often wears outfits that make it look like she's posing behind the cellophane panel of a cardboard box.

Carpenter's love of platform boots and gluteal sulcus-skimming hemlines give her that Bratz-like quality. On Reddit, she's also been likened to the dolls' animated counterparts, the "Winx Club" pixies, or an even tinier toy: Polly Pocket. But the "Espresso" singer does not browse the toy aisle when searching for style inspo. "I look at old photos of Brigitte Bardot and Jane Birkin and even young Dolly [Parton]; a lot of the things they wore feel very close to the things that I like to wear now," she told W magazine in 2024. We can see the vision here in some of her outfits, which are adorbs and harmless fun for the most part, but a few of her looks have been utter nonsense or even somewhat controversial.

There's nothing wrong with switching it up like Nintendo from time to time, but Sabrina Carpenter's 2017 American Music Awards ensemble was the sartorial equivalent of Tetris' infuriating "game over" sound. It was a departure from her ultra-girly style that landed her on E! News' worst-dressed list for being too casual for the event.

The fabric was what slashed her gown's style value. If someone told a plaid-loving dad that he needed to add more color to his wardrobe, he might go out and buy a shirt constructed from similar rainbow-colored material. When shaped into the silhouette of Carpenter's coat dress, which had a deep neckline and long sleeves, the end result was reminiscent of a bathrobe, albeit an impeccably tailored one. Another issue was Carpenter's footwear choice. Her thigh-high boots were almost the same color as her skin, so from a distance, it looked like she had really wrinkled legs.

Six years after that outfit miscalculation, Carpenter told Glamour, "I think I'm in that head space right now where I'm like, 'I'm young, I have to wear this all before it looks a little crazy.'" However, her American Music Awards dress is proof that it's possible to try to go bold and fail at pulling it off no matter how old you are. Now, if she had done the same look in neon plaid with different shoes, maybe she would have given us rad rather than espresso-sipping dad.

Sabrina Carpenter joined the list of musicians who have angered religious groups when she dropped her music video for her 2023 single "Feather." Part of the video was filmed at the Annunciation of the Blessed Virgin Mary Church in Brooklyn, where Carpenter danced in front of an altar upon which some pastel-colored coffins were on display. She was rocking her take on mourning attire: a black tulle puff dress, matching lace veil, sheer black tights, and stilettos. She looked like a sacrilegious loofah, and she got scolded by the National Review for showing off her undies inside a place of worship.

The church was considered desecrated after Carpenter and her team shot the video there, according to the Catholic News Agency, so the church held a special service called a mass of reparation. "Through the offering of this Mass, Bishop Brennan has restored the sanctity of this church and repaired the harm," said the Diocese of Brooklyn. The pastor who authorized the filming also lost his administrative role with the church.

Of the controversy, Carpenter quipped to Variety that it was all good because the son of man is her fam: "Jesus was a carpenter," she said. She later performed at Coachella wearing a shirt emblazoned with the same sentence, which probably also didn't go over so well with anyone who considered her music video blasphemous.

A "Nonsense" outro about the naked dress that Sabrina Carpenter wore to the 2023 Vanity Fair Oscar party might go a little something like this: Sabrina, get your stylist on the phone. That see-through mesh doesn't match your skin tone. And what's up with the weird bedazzling beneath your breastbone?

The sheer fabric of the bodice and sleeves of Carpenter's Paco Rabanne gown was slightly paler than her sun-kissed skin color, which was a minor annoyance that's not unusual for a naked dress. A pair of multi-colored, bejeweled pasties were attached to it, and they shared the same bizarre shape — they looked like two fists clad in Infinity Gauntlets flipping the bird. Then there was the singer's plain white skirt, which dipped down to create a V beneath her belly button. It desperately needed some color to create some cohesion with the embellishments on the top half of the dress. 

Carpenter told Who What Wear that she received the same gown in black, and the darker color also would have been much easier on the eye. However, she was feeling the white when she slipped that one on. "It was, I feel like, a different look for me than I would normally go for," Carpenter said of what she found so appealing about it — but so would be dressing up like a banana, a fruit she despises "on a spiritual level."

Taylor Swift used the lyrics of "thanK You aIMee" to fire shots at Kim Kardashian in their long-standing feud, letting it be known that she has not forgiven and forgotten. So, how could Sabrina Carpenter accept a job offer from Kardashian knowing this?

When Carpenter was asked to be the opening act for Swift's international Eras Tour stops, she joked that she almost suffered an uncomfortably damp wardrobe malfunction. "I'm not gonna say I peed my pants because that sounds really graphic and maybe not sanitary," she told Who What Wear. She also revealed that she had developed a sisterly bond with Swift. With all of this in mind, it should come as no shocker that Swifties were upset when they saw the "Skin" singer promoting a variety of lingerie sets from Kardashian's SKIMS brand. 

Carpenter launched her racy campaign on Instagram on April Fools' Day in 2024, but it was no prank. Swifties certainly didn't find it amusing — they inundated the post with comments expressing their disapproval. "Partnering with Kim K after everything Taylor has done for you? Shady. At least your true character is now showing," one Instagrammer wrote. "Can't believe you betrayed Taylor like that," admonished another. However, others argued that Swift would be understanding of her friend doing what it takes to secure the bag.

Sabrina Carpenter was a Miley Cyrus fan growing up, and it showed when she performed at 2024 Coachella. For one stage appearance, she rocked a Roberto Cavalli ensemble consisting of a micro pleated miniskirt that was a Y2K throwback, a snakeskin-print jacket that looked as if it had been doused in bleach, and a crystal-coated top with a raw hem. She replaced her beloved white go-go boots with a pair in brown.

The "Hannah Montana" costume team could have put the singer's outfit together, except the Disney Channel probably would have insisted on the skirt being much longer. Carpenter herself admitted that she thinks the skirts she wears on stage might be a tad too tiny but told Who What Wear, "There's like this part of me right now that I'm like, 'I'm gonna wear short skirts as long as I can,' and this is the era that we're in currently." Well, she could actually wear short skirts until she's 90 if she wants to, but it would make her outfits more successful if she styled them right.

The tweenage drama queen vibes just felt like a step backward for Carpenter style-wise, and at a huge music festival, no less. But perhaps for her, this is moving forward in fashion. "The things I feel really confident in now, maybe five years ago I probably would have never worn [them]," she told Who What Wear, "but that's the beautiful thing about evolving with fashion."