Taylor Swift’s Most Memorable Red Carpet Fashion Moments

From demure dresses to bold and daring choices, Taylor Swift’s red carpet evolution mirrors her transition from country sensation to the global pop icon she is today.

Image: Taylor Swift at the 2023 Grammys.
Taylor Swift’s red carpet evolution is one to watch. Variety via Getty Images

Taylor Swift’s red carpet style evolution is a testament to her journey in the music industry. From her beginnings as a fresh-faced country singer at the age of 14, Swift quickly won the hearts of many with her heartfelt lyrics and multi-instrumental talent. Her early years were marked by a sweet, girl-next-door image, reflecting the down-to-earth charm that endeared her to fans and dedicated Swifties worldwide. As her career flourished, so did her style, transitioning from demure dresses to bold and daring choices that paralleled her transition from country sensation to global pop icon.

Although Swift achieved notable success in the early aughts, she has truly reached her peak in recent years. Her decision to re-record her earlier works, a bold move towards reclaiming artistic ownership, catapulted her even further into the spotlight, sparking renewed enthusiasm among fans. The ongoing Eras Tour, celebrating her musical journey, showcases her hits from different phases of her career, and already set a record for the highest-grossing tour by a female artist (and the second highest-grossing tour ever).

As an artist, Swift isn’t afraid to push boundaries, occasionally embracing daring and eclectic styles, which extends to her fashion choices. She skillfully aligns her wardrobe with the themes of her records, showcasing a dynamic range in her public appearances. Yet, amid this versatility, there are certain mainstays that consistently shine through in her red carpet looks.  

Some of the defining elements of Swift’s red carpet style include her affinity for shimmery metallics, sequins and dazzling jewelry (often by Lorraine Schwartz). Her iconic red lip, too, has become a signature element of her personal style. With every red carpet appearance, Taylor Swift continues to captivate the world, not only with her music but also with her ever-evolving sense of style. 

Ahead, see Swift’s most memorable red carpet fashion moments through the years. 

Subscribe to Observer’s Lifestyle Newsletter

Image: Taylor Swift at the 2006 CMT Music Awards.
Taylor Swift. FilmMagic

2006, CMT Music Awards 

Swift made her red carpet debut at the 2006 CMT Music Awards. Embodying her emerging status as a country singer, she chose a white midi dress with black western-style accents by Karen Millen and matching heels. While not necessarily her standout style moment, it was nonetheless a significant night for Swift, as she took home the Breakthrough Video of the Year award for her debut single, “Tim McGraw.” 

Image: Taylor Swift at the 2007 Academy of Country Music Awards.
Taylor Swift. FilmMagic

2007, 42nd Academy of Country Music Awards 

Swift made a memorable red carpet entrance at the 2007 Academy of Country Music Awards. While she didn’t end up taking home an award that night, she certainly wore a best-dressed-worthy custom gown from Sandi Spika Borchetta (a music exec married to Scott Borchetta, the head of Swift’s then-record label, Big Machine Records) which she accessorized with drop diamond earrings. 

Image: Taylor Swift at the 2008 Grammy Awards.
Taylor Swift. WireImage

2008, 50th Grammy Awards

Just a few years into her career, Swift received her first Grammy nomination for Best New Artist and also served as one of the presenters. For the occasion, Swift wore another custom violet gown by Sandi Spika in a similar silhouette to her CMA dress, and accessorized with simple drop diamond earrings, along with her then-signature curls. 

Image: Taylor Swift at the 2008 Met Gala.
Taylor Swift. Getty Images

2008, Met Gala 

Swift attended her very first Met Gala in 2008, when the theme was “Superheroes: Fashion and Fantasy.” Swift donned a sparkly gold gown (which is rather evocative of the current mermaidcore trend) from Badgley Mischka’s Fall 2008 collection. 

Image: Taylor Swift at the 2009 Academy of Country Music Awards.
Taylor Swift. FilmMagic

2008, 43rd Academy of Country Music Awards 

In 2008, Swift won her first ACM for New Female Vocalist of the Year, and wore a strapless white Marchesa gown adorned with gold beadwork, paired with matching silver earrings and a bracelet that added a touch of refinement. 

Image: Taylor Swift at the 2009 Grammys.
Taylor Swift. FilmMagic

2009, 51st Grammy Awards 

For the 2009 Grammys, Swift wore an elegant floor-length gown from Kaufmanfranco’s Fall 2009 collection, along with a Loraine Schwartz gold cuff and matching drop earrings. Although she wasn’t nominated, she took the stage in a performance of “Fifteen” alongside Miley Cyrus. 

Image: Taylor Swift at the Hannah Montana: The Movie premiere.
Taylor Swift. WireImage

2009, “Hannah Montana The Movie” Los Angeles Premiere 

Swift turned heads in a strapless, sequined cocktail dress from Naeem Khan’s Ready-to-Wear Fall 2009 collection at the Los Angeles premiere of Hannah Montana: The Movie. She paired the frock with black Christian Louboutin heels, and added a bit more sparkle to her look with a cuff and ring from Swarovski.   

Image: Taylor Swift at the 2009 VMAs.
Taylor Swift. FilmMagic

2009, MTV Video Music Awards

At the VMAs, Swift opted for a silver sequined Kaufmanfranco gown, complemented by a curly updo and, of course, a bright red lip. Later that evening, she won the award for Best Female Video for “You Belong With Me,” a moment infamously marked by Kanye West’s interruption of her acceptance speech. 

Image: Taylor Swift at the 2010 Grammy Awards.
Taylor Swift. WireImage

2010, 52nd Grammy Awards

Swift began the night at the 2010 Grammys in a custom Kaufmanfranco sequined off-shoulder gown. While a memorable style choice, the awards show also marked a career-defining moment for Swift. She secured a record-breaking achievement with eight nominations, and won Album of the Year and Best Country Album for Fearless, as well as Best Female Country Vocal Performance and Best Country Song for “White Horse.” Notably, Swift was the youngest recipient of Album of the Year at the time. Later in the evening, she performed a solo rendition of “Today Was a Fairytale” and then a duet of “Rhiannon” and “You Belong With Me” alongside the legendary Stevie Nicks. 

Image: Taylor Swift at the 2010 Met Gala.
Taylor Swift. Corbis via Getty Images

2010, Met Gala 

At the 2010 Met Gala, Swift embraced the “American Woman: Fashioning a National Identity” theme in an elegant white gown from Ralph Lauren, along with a Fred Leighton bracelet and diamond drop earrings, plus a diamond ring by Lorraine Schwartz. And, of course, a classic red lip. 

Image: Taylor Swift at the Easy A Los Angeles Premiere.
Taylor Swift. WireImage

2010, “Easy A” Los Angeles Premiere 

Swift attended the Easy A Los Angeles premiere in a striking green silk Miu Miu mini dress, along with gold Christian Louboutin platform pumps. 

Image: Taylor Swift at a CoverGirl Event in 2011.
Taylor Swift. Jeff Vespa

2011, CoverGirl Event

To celebrate CoverGirl’s 50th Anniversary, Swift chose a strapless sequin dress by Badgley Mischka, which she paired with embellished satin Dolce & Gabbana heels and a loose updo. 

Image: Taylor Swift at the 2011 AMAs.
Taylor Swift. FilmMagic

2011, American Music Awards 

Swift had a night to remember at the 2011 AMAs, as she won all three awards for which she was nominated, including Artist of the Year. She radiated confidence in a strapless, gold sequined gown from Reem Acra’s Spring 2012 Ready-to-Wear collection and wore her hair in a loose side ponytail. 

Image: Taylor Swift at the 2012 Grammys.
Taylor Swift. WireImage

2012, 54th Grammy Awards 

Swift’s red carpet style began to evolve into more mature looks, as seen at the 54th Grammys. She stuck with her favored metallic hues and embellishments in a Zuhair Murad couture gold gown, but in a more sophisticated silhouette featuring a high neckline. She opted for a slicked-back hairstyle instead of her signature loose updo. While she didn’t win as many Grammys as she did in 2010, she still received awards for Best Country Song and Best Country Solo Performance for “Mean.”

Image: Taylor Swift at the 2012 VMAs.
Taylor Swift. FilmMagic

2012, MTV Video Music Awards

She wasn’t nominated for a VMA in 2012, but Swift nonetheless took center stage with a performance of “We Are Never Ever Getting Back Together.” Instead of the expected red carpet dress, Swift showcased a more mature sense of fashion in a sophisticated white tuxedo suit from J. Mendel and gold stilettos from Tom Ford. 

Image: Taylor Swift at the 2013 People's Choice Awards.
Taylor Swift. Getty Images for PCA

2013, 39th People’s Choice Awards 

Swift exuded timeless elegance at the People’s Choice Awards in a striking long gown from Ralph Lauren. She completed her look with a pair of blue drop earrings from Sutra, adding a pop of color to her otherwise simple look. Later that evening, she served as one of the presenters and won the award for Favorite Country Artist. 

Image: Taylor Swift at the 2013 Brit Awards.
Taylor Swift. WireImage

2013, Brit Awards

Swift’s outfit at the Brit Awards was a refreshing departure from her previous red carpet appearances, signaling a shift toward an edgier sense of style. She opted for a belted black gown from Elie Saab’s Fall 2013 Ready-to-Wear collection, and accessorized with a gold cuff that complemented her belt. She switched up her hair, too, with a simple, straight style and her now-signature bangs.

Image: Taylor Swift at the 2013 AMAs.
Taylor Swift. WireImage

2013, American Music Awards 

Following the 2012 release of Red, Swift’s career successes matched her elevated red carpet style. She turned heads as she was dressed in a gold Julien Macdonald mini dress and strappy gold Jimmy Choo heels. Her fresh, soft waves added a touch of romance to her overall look. 

Image: Taylor Swift at the 2014 Victoria's Secret Fashion Show.
Taylor Swift. WireImage

2014, Victoria’s Secret Fashion Show

Swift amped up the glamour at the 2014 Victoria’s Secret Show, in a strapless J. Mendel mini dress with silver detailing, along with patent Jimmy Choo heels. Just a month prior, she had released her first official pop album, 1989, marking a notable shift in her artistic style, and she performed both “Blank Space” and “Style” later that evening on the catwalk.  

Image: Taylor Swift at the 2015 iHeartRadio Music Awards.
Taylor Swift. FilmMagic

2015, iHeartRadio Music Awards 

Not only did Swift deliver a memorable performance alongside Madonna, showcasing her guitar skills on “Ghosttown,” but she also scored the most wins of the year at the 2015 iHeartRadio Music Awards. Her red carpet look was equally noteworthy, in the form of a striking black mini cutout dress from Kaufmanfranco and black Tamara Mellon heels. 

Image: Taylor Swift at the 2015 BBMAs.
Taylor Swift. Getty Images

2015, Billboard Music Awards

Swift’s red carpet look at the Billboard Music Awards encapsulated her signature blend of elegance and edginess. Swift appeared in a white cutout jumpsuit from Balmain’s Spring 2015 collection, designed by Olivier Rousteing, and accessorized with a custom clutch from Edie Parker.  Aside from her fashion wins, Swift dominated at the show, winning eight awards out of her 14 nominations, including Top Artist, Top Female Artist and Top Billboard 200 Album for 1989. Swift’s achievements made her the standout artist of the night, boasting the most wins and nominations. 

Image: Taylor Swift at the 2016 Grammys.
Taylor Swift. AFP via Getty Images

2016, 58th Grammy Awards

At the 2016 Grammys, Swift opted for an eye-catching Atelier Versace two-piece gown in vibrant shades of orange and pink, paired with strappy gold heels from Stuart Weitzman. Her short haircut added a chic element to the overall look. The evening became even more momentous when she performed “Out of the Woods” and won two Grammys for 1989.

Image: Taylor Swift at the 2016 Vanity Fair Oscar Party.
Taylor Swift. Getty Images

2016, Vanity Fair Oscar Party 

Swift’s dramatic black Alexandre Vauthier gown at the 2016 Vanity Fair Oscar party featured a plunging neckline and bold gold detailing, and was somewhat reminiscent of her 2013 Brit Awards ensemble. This time, Swift elevated her look with a sleek, short hairstyle. 

Image: Taylor Swift at the 2016 Met Gala.
Taylor Swift. Getty Images

2016, Met Gala 

Swift wore perhaps her most on-theme Met Gala look to the 2016 extravaganza, for which she was a co-host. For “Fashion in the Age of Technology,” Swift arrived in an avant-garde ensemble that stands as one of her most daring red carpet choices to date: a strikingly futuristic, space-age look composed of a Louis Vuitton metallic snakeskin mini dress and a pair of cutout sandals. Complementing the ensemble were matching silver jewelry pieces, along with a dramatic, near-black lip. 

Image: Taylor Swift at the 2018 AMAs.
Taylor Swift. Getty Images For dcp

2018, American Music Awards 

Swift won all four categories for which she was nominated at the 2018 AMAs, tying with Camila Cabello for most awards of the evening. After a three-year absence, Swift returned in a fittingly glamorous look, donning a long-sleeved metallic mini dress and matching boots from Balmain’s Spring 2019 collection.  

Image: Taylor Swift at the 2019 iHeartRadio Music Awards.
Taylor Swift. Getty Images for iHeartMedia

2019, iHeartRadio Music Awards

At the 2019 iHeartRadio Music Awards, Swift returned to her love for sequins and metallics with Rosa Bloom’s Mella Cape playsuit paired with silver heels from Sophia Webster. The dreamy color and silhouette also perfectly aligned with the motifs for Lover, which debuted later that year.

Image: Taylor Swift at the 2019 Time 100 Gala.
Taylor Swift. WireImage

2019, Time100 Gala

Mere days before releasing the first single from Lover, Swift graced the Time100 Gala with a performance of “Style” and “Delicate.” Swift chose a J. Mendel strapless gown in a vibrant coral shade, embellished with yellow floral embroidery signaling the spring season—that, and the aforementioned Lover theme. She completed her look with a floral headband that adorned her loose updo. 

Image: Taylor Swift at the Cats World Premiere in 2019.
Taylor Swift. FilmMagic

2019, Cats World Premiere

Despite the 2019 Cats adaptation’s mixed reviews, Swift’s highly-anticipated role as Bombalurina was well-received. Swift attended the premiere in an elegant Oscar de la Renta floral gown and red strappy sandals by Chloe Gosselin. 

Image: Taylor Swift at the world premiere of Taylor Swift: Miss Americana.
Taylor Swift. Getty Images

2020, Sundance Film Festival: Taylor Swift: Miss Americana Premiere 

In one of her last red carpet appearances before the COVID-19 pandemic, Swift celebrated the premiere of her Netflix documentary film, Taylor Swift: Miss Americana. Swift chose a houndstooth ensemble consisting of a matching jumpsuit, trench coat and heels by Carmen March. 

Image: Taylor Swift at the 2021 Grammys.
Taylor Swift. Los Angeles Times via Getty Images

2021, 63rd Grammy Awards

Swift made her first red carpet appearance since the onset of the COVID-19 pandemic at the 2021 Grammys. She chose a very on-point, spring-ready ensemble, with an Oscar de la Renta floral embroidered tulle dress and Christian Louboutin pink suede heels. Later that evening, she won Album of the Year for Folklore. 

Image: Taylor Swift at the premiere of All Too Well The Short Film in 2021.
Taylor Swift. Getty Images

2021, “All Too Well” New York Premiere 

It seemed like everyone was suddenly the biggest Swiftie when the short film for the ten-minute version of “All Too Well” was released. Starring actors Sadie Sink and Dylan O’Brien, the project earned numerous awards and nominations. Notably, this also marked Swift’s filmmaking debut, making the project’s success even more special. For this momentous occasion, Swift donned a striking purple velvet suit by Etro, paired with Alexandre Birman boots. 

Image: Taylor Swift at the 2022 VMAs.
Taylor Swift. Variety via Getty Images

2022, MTV Video Music Awards

Swift paired this dazzling, crystal-embellished Oscar de la Renta mini dress with equally glitzy silver Christian Louboutin heels. Needless to say, she radiated an air of glamour and opulence. 

Image: Taylor Swift at the EMAs 2022.
Taylor Swift. WireImage

2022, MTV Europe Music Awards

Swift was the undisputed star at the 2022 MTV Europe Music Awards. Clinching the most awards of the evening, Swift took home Best Video and Best Longform Video for All Too Well: The Short Film. Swift looked the part in a stunning dress with emerald detail from David Koma’s Autumn/Winter 2022 collection, paired with stilettos from Giuseppe Zanotti. 

Image: Taylor Swift at the 2023 Grammys.
Taylor Swift. Getty Images for The Recording Academy

2023, 65th Grammy Awards 

Swift received four nominations and won Best Music Video for “All Too Well: The Short Film” at the 2023 Grammys. Swift made a powerful statement in a custom Roberto Cavalli gown and an exquisite array of Lorraine Schwartz jewelry. The baubles were valued at nearly $3 million, according to Variety, with over 136 carats of “natural purple sapphires, paraibas and diamonds” on the earrings alone. 

Image: Taylor Swift at the premiere of Taylor Swift: The Eras Tour in 2023.
Taylor Swift. AFP via Getty Images

2023, “Taylor Swift: The Eras Tour” Premiere 

For the premiere of Taylor Swift: The Eras Tour, Swift chose a cutout floral gown by Oscar de la Renta, paired with matching heels from Giuseppe Zanotti. She accessorized with a tennis bracelet, necklace and earrings from Cartier to add a touch of opulence to her look. The film, which she produced herself, became the highest-grossing concert film of all time less than a month after its debut.

Taylor Swift’s Most Memorable Red Carpet Fashion Moments