Olivia Rodrigo has been in the spotlight since her pre-teens but it seems that her star is continually on the rise. Though she is most known for her musical prowess, the California-native got her start in acting via kiddie comedy series Bizaardvark. Shortly after, she landed the then biggest role of her young career as Nini Salazar-Roberts in the Disney+ series High School Musical: The Musical: The Series (which she eventually left in 2022 to focus on music.)

In only a few years, Rodrigo has gone from Disney star to reigning pop-punk princess, not only thanks to her critically-acclaimed albums Sour and GUTS, but also due to her unique style sense. On the red carpet, she’s gravitated towards bright, Gen Z styles that are never without an added edge. She’s championed designers both rising and established—from vintage Versace and Miu Miu to Ludovic de Saint Sernin and Fancí Club. Through it all, Rodrigo has cemented herself as one of the most exciting voices in music and fashion. Below, take a look back at Olivia Rodrigo’s best red carpet moments from High School Musical to now.

2026: Met Gala After Party

Though she skipped the main event, Rodrigo popped into Saint Laurent’s Met Gala after party in a knitted archival Vivienne Westwood mini dress from 1994.

2026: Vanity Fair Oscar Party

Rodrigo went for party girl opulence at VF’s big Oscars bash. Her pink fathered dress was custom Saint Laurent.

2026: Paris Fashion Week

Rodrigo made a rare Paris Fashion Week appearance to catch the Chloé show. She was wearing of course head-to-toe Chloé.

2025: Lily Allen’s Christmas Party

Rodrigo attended Lily Allen’s Christmas shindig in London in a dress that’s older than she is. Her lacy number is from Tom Ford’s spring 1996 collection for Gucci.

2025: Academy Museum Gala

At the 2025 Academy Museum Gala, Rodrigo scoured the archives for this elegant Armani Privé two-piece look from the label’s spring 2005 collection.

2025: Grammy Awards

The singer delivered classic va-va-voom glamour in a cut-out Versace dress at the Grammys in 2025.

2025: Guts World Tour Premiere

Rodrigo’s vintage Dior gown, designed by John Galliano in 1998, is older than she is.

2024: Grammy Awards

In a vintage Versace dress from 1995, Rodrigo embraced full old Hollywood glamour for music’s biggest night in 2024.

2024: Governors Awards

Rodrigo’s archival Saint Laurent gown, from the brand’s fall 1997 couture collection, just so happens to be three years older than she is.

2023: Variety Hitmakers Brunch

The singer ventured on the casual side for the Variety Hitmakers Brunch with this floral mini dress and platform Mary Janes.

2023: GQ Men of the Year Awards

Rodrigo slipped into this party-ready fringe dress from Tom Ford’s spring 2024 collection for the GQ Men of the Year Awards.

2023: Hunger Games: The Ballad Of Songbirds & Snakes Premiere

This Rodarte halter gown, complete with sequins and floral appliqués, fit Rodrigo like a glove during The Hunger Games: The Ballad Of Songbirds & Snakes premiere.

2023: MTV Video Music Awards

All that glitters is, well, silver. At the 2023 MTV Video Music Awards, Rodrigo dazzled in a custom Ludovic de Saint Sernin gown.

2023: Met Gala

For an impressive third Met Gala appearance at age 20, the singer went with a dramatic black and white Thom Browne look in keeping with the Karl Lagerfeld theme.

2023: Grammy Awards

Rodrigo got in on the sheer red carpet craze with this skin-baring Miu Miu dress she wore to the 2023 Grammy Awards.

2022: iHeartRadio Music Awards

Though Rodrigo took home three awards at the 2022 iHeartRadio Music event, her purple Versace mini dress and skin-tight boots were just as much of a winner.

2022: Grammy Awards

At the 2022 Grammy Awards, Rodrigo graced the red carpet in a black and purple Vivienne Westwood gown and coordinating opera gloves.

2022: Met Gala

The singer turned heads in this glittering Versace gown, complete with a sizable slit, that she paired with statement heels, voluminous hair, and butterfly clips.

2022: Driving Home 2 U Premiere

Well ahead of the current bow trend, the star sported a dainty Fancí corset and pink mini skirt to the 2022 Driving Home 2 U premiere.

2022: Billboard Women in Music Awards

This belted maxi dress from New York label Area was the ensemble of choice for Rodrigo when she attended the 2022 Billboard Women in Music Awards.

2022: Brit Awards

Rodrigo was certainly amongst the best dressed at the 2022 Brit Awards in this chainmail Alexandre Vauthier number.

2021: Opening Gala for the Academy Museum of Motion Pictures

Rodrigo was a vision in Saint Laurent for the 2021 opening gala of the Academy Museum of Motion Pictures.

2021: Met Gala

Rodrigo turned heads at the 2021 Met Gala in this lace Saint Laurent bodysuit.

2021: MTV Video Music Awards

For her first time at the MTV Video Music Awards, the songstress made quite the statement in a pastel Versace gown.

2021: Brit Awards

Rdorgio somehow made the highlighter yellow of this Dior dress work at the 2021 Brit Awards.

2021: American Music Awards

This feather and sheer David Koma look that Rodrigo wore to the 2021 American Music Awards would double as the perfect party dress.

2019: D23 Expo

Before her solo breakout, Rodrigo was a mainstay on the Disney circuit—here, she wore a white turtleneck and corduroy pants to the D23 Expo in 2019.

2018: Radio Disney Music Awards

Even as a teenager, Rodrigo still had a passion for pink and lots of sparkle.

2017: Coco Premiere

The singer was lightyears ahead of the ballet shoe trend when she wore a red lace-up pair to the Coco premiere in 2017.

2016: The Swap Premiere

15-year-old Rodrigo stepped out to The Swap premiere in a patterned chiffon dress and leather boots.

Like many Disney stars, Sabrina Carpenter has come a long, long way since her days on the network. After cutting her teeth in the likes of Girl Meets World and Tall Girl, the Pennsylvania native has gone on to forge a successful music career of her own, culminating in the smash hit “Espresso” off her album, Short n’ Sweet. While producing songs like “Nonsense” and “Taste,” Carpenter managed to forge a unique red carpet wardrobe that combines hyper-feminine silhouettes with edgy details like cut-outs and exposed undergarments.

The triple threat—she can act, sing, and dance—has cozied up to some of fashion’s top brands like Miu Miu, Louis Vuitton, and Moschino as well as independent labels like Cong Tri and Mônot. It’s become customary for Carpenter pull out a statement red carpet moment during events like the Grammys and MTV Video Music Awards, arming herself with some sort of high-impact gown (probably vintage), a bold color way or pattern, and her signature blonde bangs. Below, a look back at Sabrina Carpenter’s red carpet evolution, from pre-teen star to pure pop princess.

2026: Grammys Awards

Carpenter turned to the opulent imagination of Valentino’s Alessandro Michele for her 2026 Grammys gown. The result was dress that was heavy on ornate details and yet still felt light and youthful.

2025: Variety Hitmakers

At a 2025 Variety event, Carpenter dipped into the Ralph Lauren archives.

2025: MTV Video Music Awards

Carpenter was in a Studio 54 mood at the 2025 VMAs with this sequined lace Valentino dress and purple stole.

2025: Met Gala

Carpenter brought the no pants trend to the 2025 Met Gala with this fitted bodysuit and train from Louis Vuitton.

2025: BRIT Awards

At the 2025 BRITs, Carpenter looked ethereal in a light pink McQueen number that took inspiration from the brand’s archives.

2025: Grammy Awards

The star leaned into Old Hollywood at the 2025 Grammys, choosing a custom JW Anderson dress with a Chopard back necklace that referenced the 1964 movie What a Way To Go!

2024: Time100 Gala

Versace is one of Carpenter’s go-to brands and she looked splendid in this chainmail number at a 2024 gala.

2024: MTV Video Music Awards

If this plunging Bob Mackie gown looks familiar, it’s likely because Madonna wore it a ton during the early 1990s.

2024: Variety Power of Young Hollywood

Carpenter has never shied away from a referential red carpet look and this butter yellow Prada dress only continued that pattern. Her blinged-out gown took cues from a similar piece Kate Hudson made famous in the 2003 movie, How to Lose a Guy In Ten Days.

2024: Louis Vuitton Men’s Show

The Short n’ Sweet singer put her twist on C.E.O. suiting for Pharrell Williams’s Louis Vuitton Men’s show in Paris. She stepped out in a strong-shouldered power blazer, worn sans pants, that she accessorized with a white speedy bag, black tie, and heels.

2024: Met Gala

In a dramatic princess dress, Carpenter certainly channeled the “Sleeping Beauties” aspect of the 2024 Met Gala dress code with her custom Oscar de La Renta look.

2024: Vanity Fair Oscar Party

Carpenter sizzled in black during the Vanity Fair Oscar after party in this croc-embossed and sequined Tory Burch number.

2024: Pre-Grammy Gala

For a pre-Grammy Gala, Carpenter went simple in a ruched LBD that featured a steep side slit and floral embroidery at the waist.

2023: MTV Video Music Awards

A princess twist on the sheer red carpet trend, courtesy of Vera Wang, for the 2023 MTV VMAs.

2023: Billboard Women In Music

For the 2023 Billboard Women In Music event, the singer flashed her abs in a Cong Tri confection.

2022: American Music Awards

Carpenter indulged in a disco diva moment with this fringe matching set at the 2022 American Music Awards.

2022: The Fashion Awards

Carpenter pulled out one of her edgier red carpet moments for the 2022 Fashion Awards in London. She slipped into a mustard yellow Alberta Ferretti gown that was designed with a plunging neckline and a matching hood.

2022: MTV Video Music Awards

In an ab-baring Moschino number, Carpenter went all in on retro florals at the 2022 MTV VMAs.

2022: amfAR Gala

When she’s not in some sort of statement color or pattern, the hitmaker tends to prefer plenty of skin-baring details for her red carpet moments. Here, she sported a Mônot gown to the 2022 amfAR Gala.

2022: Met Gala

Carpenter made a splash for her debut Met Gala appearance in 2022. She sparkled in a Paco Rabanne set composed of a bra top and a high-impact skirt.

2022: Kids’ Choice Awards

The star wrapped up her cut-out David Koma dress with an exposed bra top at the 2022 Kids’ Choice Awards.

2021: ACE Awards

For the 2021 ACE Awards, Carpenter looked like red carpet royalty with this floral Carolina Herrera number.

2020: MTV Movie & TV Awards

Carpenter has dabbled in the exposed underwear trend at multiple points throughout her red carpet career, but her rhinestoned look for the 2020 MTV Movie & TV Awards proved to be her most on-the-nose adaptation yet.

2019: Tall Girl Premiere

Carpenter suited up for the premiere of Tall Girl in a plunging ivory set.

2018: Peoples’ Choice Awards

The singer looked chic in pinstripe Tom Ford at the 2018 Peoples’ Choice Awards.

2018: MTV Video Music Awards

Carpenter reinvented the bandage dress at the 2018 MTV VMAs in a va-va-voom Versace look that she paired with nude heels.

2017: Billboard Women In Music

Well before Margot Robbie graced theater screens as Barbie, Carpenter presented a full-on Mattel pink moment at a 2017 Billboard event.

2016: Kids’ Choice Awards

With a copy of Alice In Wonderland doubling as a clutch, Carpenter slipped into black and white lace for the 2016 Kids’ Choice Awards.

2015: American Music Awards

At the 2015 AMAs, Carpenter went with a patterned tea-length look that she paired with a blush pink clutch and strappy heels.

2014: Wicked Opening Night

The actress sported high-waisted floral pants and an off-the-shoulder top to the opening night of Wicked in 2014.

2013: Kidstock Festival

Alongside fellow Disney actress Rowan Blanchard, Carpenter looked adorable at a 2013 festival.

2012: Once Upon A Princess Premiere

Then 12, Carpenter attended one of her first red carpets for the premiere party of Disney’s Once Upon A Princess.

Gird your loins! The Devil Wears Prada 2 press tour is off to the races—and Anne Hathaway is wearing the boots. Just not the Chanel ones.

For her first appearance to promote the much-anticipated sequel, alongside Meryl Streep, Hathaway slipped into a full look from Stella McCartney’s fall 2026 runway show. She sparkled in a fully-sequined, bright pink dress complete with long sleeves and a flared mini skirt. Despite the dress’s dazzling, sequin-heavy finish, her shoes proved to be the real scene-stealers.

Hathaway finished the look with heeled black boots that climbed so high they nearly met the hem of her dress. Where’s Emily Blunt to ask, “Are you wearing the Stella McCartney boots?” when you need her?

Streep, for her part, also brought the fashion. She wore a blue (navy, not cerulean) shirt dress from Schiaparelli, complete with gold buttons down the front and a cinched statement belt. Streep styled the floor-length piece with a surreal face bag and tooth-shaped earrings, both from Schiaparelli.

Hathaway and Streep kicked off their tour earlier in the day when they attended a press conference at the Frida Kahlo Museum in Mexico City. This time, it was Hathaway wearing Daniel Roseberry’s fantastical Schiaparelli creations. She looked sleek in a black fringe dress with gold detailing along the bustier, paired with keyhole Schiaparelli pumps and tinted glasses and jewelry by Bulgari. Streep channeled TDWP red with her outfit. Looking like she had stepped right out of Miranda Priestly’s office, the actor wore a monochromatic Dolce & Gabbana suit, along with cat-eye glasses from Emmanuelle Khanh.

After their first stop in Mexico, Anne Hathaway and Meryl Streep are taking their press tour global ahead of The Devil Wears Prada 2’s theatrical release, with stops planned in Tokyo, Shanghai, London, and New York. Consider last night the start of a full-fledged fashion marathon.