Believe it or not, Sabrina Carpenter isn't a Grammy Awards veteran: She actually made her debut at the show in 2025, a full decade after she released her first studio album. On February 1, Carpenter returned to the red carpet for the 2026 Grammy looking every bit a regular.
With six Grammy nominations this year—ranging from Album of the Year to Song of the Year—stylist Jared Ellner knew all eyes would be on Carpenter. So, he worked with Valentino to create a bespoke white gown with understated nakedness.
Nude underlay lined the entire floor-length look, beginning with an intricately-beaded floral bodice. Short, cape-like sleeves gave the Alessandro Michele design a surprising boho-chic feel, perhaps inspired by Man's Best Friend tracks like "My Man On Willpower" and "Sugar Talking." Partially transparent tiered ruffles covered the skirt—zoom in to appreciate each layer's pearl polka dots, which decorated Carpenter's sleeve-shawl hybrid, too.
Carpenter is building quite the impressive Grammys look book. (At this rate, she'll have one to rival Lady Gaga's before her 30s.) Contrary to her flirty, everyday and on-stage outfits, her 2025 Grammys gown awoke her glamorous, Old Hollywood-inspired side: Designed by Jonathan Anderson (a.k.a. Dior's creative director) for his own label, J.W. Anderson, the halter-neck design featured a nostalgic feather trim lining the drop waist and flared hem. She worked with stylist Andrew Mukamal on the look, which still felt Carpenter-coded to a T. (Its soft shade of baby blue has been the singer's signature since 2024's Short n' Sweet era.)
The vintage-inspired cherry on top of Carpenter's cake was the dress's strap-necklace hybrid, made up of nearly 70 carats of Chopard diamonds that looped through the satin bodice before cascading down her entirely open back. All eyes went to the chain's 50-carat pear-shaped pendant, courtesy of the jeweler's Garden of Kalahari collection.
What began as an homage to fellow blonde bombshell Shirley Maclaine in 1964's What a Way to Go! transformed into a full-blown red carpet trend. Similar styles frosted the backs of Margaret Qualley and Michelle Yeoh at the 2025 Oscars, as well as Taylor Russell and Ariana Greenblatt at the 2025 Cannes Film Festival.
Carpenter accepted both of her Grammys in another, equally-glamorous gown, this time by Atelier Versace. The strapless bustier dress's metallic gold rhinestones sparkled just as much as her trophies, especially on the Crypto.com Arena's stage. Once again, Chopard loaned the "Espresso" singer a diamond drop necklace, stud earrings, and a statement ring.
It may have been her first Grammys, but Carpenter already got plenty of sartorial practice before walking the red carpet last year. She's been attending numerous pre- and post-ceremony soirées since 2019.
In 2023, Carpenter RSVP'd "yes" to Universal Music Group's after-party. Her crop top and cutout-heavy Giuseppe Di Morabito set ended up on best-dressed lists galore. Three-dimensional silver flowers atop the skirt's side slit elevated the year's rosette trend.
The rosette motif resurfaced on Carpenter's little black dress at Clive Davis's 2024 Pre-Grammy Gala. The pop star stole the show in a turtleneck, cap-sleeve gown from David Koma, with a rhinestoned rose at the waist, sitting atop a thigh-high slit.
At the time, Carpenter was still months away from establishing the aesthetic you know and love her for today. Once "Espresso" dropped in April 2024, the babydoll minis, hot pants, and micro-mini skirts took over. Now, with her style as recognizable as her music, Carpenter's Grammy Award gowns will only get more fabulous from here.
