2006 ACM Awards
For her first Academy of Country Music Awards — which took place just a few weeks before her debut single “Tim McGraw” dropped — Swift wore a perfectly country dress with a handkerchief hem and, naturally, cowboy boots. She would return to the show the following year to collect the award for New Female Vocalist of the Year.
2007 CMT Music Awards
For the 2007 CMT Music Awards, where she won Breakthrough Video of the Year for “Tim McGraw,” Swift maintained her princess profile by bringing back this iridescent, aquamarine dress from the wistful “Teardrops on My Guitar” music video while wearing her long curly hair loose.
“Our Song” music video (2007)
For this joyous, consciously girly clip, Swift sang about a “slammin’ screen door” and “sneakin’ out late, tappin’ on your window” while wearing a periwinkle corset and tulle skirt.
2008 Grammy Awards
Swift’s 2008 Grammys look recalled the frothy gown from the “Our Song” video, but glammed it up for the carpet, coming in a darker shade with floral embellishments.
“Love Story” music video (2008)
Swift wasn’t shy about rearranging classic literature with her “Love Story” lyrics (that’s not how Romeo and Juliet ends, kids!), but she kept the wardrobe old-school. Her cream-colored dress in the romantic music video was made in her then-favorite style of drop-waisted corset dresses, keeping up her distinctly fairy-tale image.
“You Belong With Me” music video (2009)
Here come the white dresses! While Swift’s band-geek uniform and Junior Jewels T-shirt in the “You Belong With Me” video are obviously iconic, her arrival at the prom in this sweet white dress (the first of many) marks her full self-actualization as both a nerdy young woman in love and a white-dress-wearing singer of swoony country-pop songs.
“Fifteen” music video (2009)
And here’s a more casual take! In the “Fifteen” music video, Swift slowly cat-walked through her new high school while reflecting upon growing up, as all innocent first-year students do, while wearing a ruffled white dress and loose hair.
2009 MTV VMAs
Swift was swept into a very strange narrative (which she would very much like to be excluded from, even now) when she won the Moonman for “You Belong With Me” at the 2009 MTV VMAs. Luckily, she was dressed for the spotlight in this glittering-Greek-goddess gown by KaufmanFranco, a more grown-up look than her princess dresses of the past. (That’s not to mention the more grown-up lip color, of which we promise there will be more…)
2010 Grammy Awards
Swift dressed for her big night — winning Album of the Year, among three other awards — at the 2010 Grammys as a mermaid rather than a princess, choosing a glittering blue gown by KaufmanFranco.
2010 Met Gala
The 2010 Met Gala theme was “American Woman: Fashioning a National Identity,” which suited Swift well. The singer appeared in a ruffled white dress that aligned perfectly with her own romantic style, as well as the Met’s theme, coming from the all-American Ralph Lauren.
Speak Now tour (2011)
Swift began to let her flashy side out during the Speak Now era, for which she wore a fringed, beaded gold dress — with black cowboy boots, because these were still her country days, lest we forget — while touring the album.
2012 Grammy Awards
Swift glittered in Zuhair Murad couture at the 2012 Grammys, in a sophisticated silhouette that marked a departure from her princess-style days.
2012 Billboard Music Awards
For the BBMAs in the spring of 2012, the star appeared without her signature curls, instead sporting straight hair and blunt bangs. The sleeker ‘do matched her Elie Saab dress, the color of which also departed from the sweet pastels of days past — and also, possibly, was a clue to the title of her next album…
It was back to white for Swift at the VMAs in 2012, where she wore — gasp! — a chic pantsuit instead of a dress. Get used to those clean lines — and that red lipstick.
“22” music video
Swift posed through the “22” music video in a shimmery T-shirt that read “NOT A LOT GOING ON AT THE MOMENT,” black shorts, a black hat, and heart-shaped sunglasses that matched her now-constantly red lips. The look firmly established the pared-down, retro-cool (but quirky — the sunglasses!) vibe of the Red era.
“Begin Again” music video
When Red-era Swift wasn’t dressed as a slightly-too-polished hipster, she went more literally retro, looking like a 1950s ingénue in fitted dresses and cardigans, like in the “Begin Again” music video.
2012 iHeartRadio Music Festival
Swift brought the new era to the stage at the iHeartRadio Music Festival in 2012 (and then on the Red tour) in costumes that matched her “22” video look — but with just a little more sparkle.
2013 Grammy Awards
Through it all, Swift’s commitment to airy white dresses has never wavered (um, except maybe until Reputation), and she hit the Grammys carpet in 2013 in this Grecian-glam look by J. Mendel — a sleeker version of her 2009 VMAs dress.
2014 Grammy Awards
Who says simplicity can’t make a statement? The singer sparkled at the 2014 Grammys in this Gucci Première column dress.
2014 Met Gala
Once again, the Met Gala theme seemed designed specifically for Taylor Swift in 2014, when the ball celebrated Charles James. The legendary designer’s elegant style lined up perfectly with Swift’s penchant for ’50s silhouettes, and she chose a very on-theme pale pink Oscar de la Renta gown for the occasion.
Swift’s outfit at the 2014 VMAs, which took place in the lead-up to 1989, marked a new irreverence and a departure from the ultra-femininity of the previous era. She played with proportion in a long-sleeved, short alphabet-printed romper by Mary Katrantzou, topping the look with red lips and chopped hair.
“Blank Space” music video
The self-aware — and exceptionally stylish — “Blank Space” music video made clear that Swift was over being the midcentury sweetheart and the sexy hipster that she alternately dressed as in the Red era. She went through a whole slew of fabulous costumes in the clip as a daydream-turned-nightmare, but none expresses the evolution better than this leopard-print blouse, smeared eye makeup, and haywire expression.
1989 tour with Selena Gomez (2015)
The album 1989 was all about crop tops for Taylor Swift (keep reading!), and on the album tour — during which she famously brought dozens of her BFFs to the stage — she often wore this bejeweled two-piece outfit in one of her all-time favorite colors.
1989 tour with Ellen DeGeneres (2015)
Swift also brought some full-blown showwoman sparkle to her 1989 show, and Ellen DeGeneres apparently loved the look so much, she copied it for her appearance on the tour.
2015 Grammy Awards
Mid-2010s Swift never met a cutout she didn’t like, as evidenced by the teal ombré Elie Saab she wore to the Grammys in 2015.
2015 Billboard Music Awards
We weren’t lying about the cutouts! Or the white! Swift looked sharp at the 2015 BBMAs — but not as sugary-sweet as her earlier all-white looks — in a sequined, floor-skimming jumpsuit by Balmain.
The crop top queen made a bit of an edgy choice when she hit the 2015 VMAs — where she presented her dear old pal Kanye with the Video Vanguard Award — in a sequined houndstooth tracksuit by Ashish.
2016 Vanity Fair Oscar party
Swift was the epitome of sleek in Alexandre Vauthier couture at the Vanity Fair Oscars party in 2016.
2016 Grammy Awards
Swift stuck to the clean lines and sleek fabrics she favored throughout the 1989 years, but went with a bold palette at the 2016 Grammys in a lipstick-red crop top over a voluminous hot pink maxi skirt by Atelier Versace.
2016 Met Gala
Taylor first dipped her toe in the dark side at the 2016 Met Gala, the theme for which was “Manus x Machina: Fashion in the Age of Technology.” The singer topped her Louis Vuitton minidress with lightened hair and darkened lips—and took the new look all the way to the dance floor with Tom Hiddleston.
2016 Fourth of July party with Gigi Hadid and Cara Delevingne
Swift’s hottest accessory of the 1989 era? Her squad, naturally. They didn’t just coordinate their wardrobe to play a team of badass fighters in the “Bad Blood” music video, they also sported matching patriotic swimsuits, memorialized on Instagrams, for Swift’s highly photogenic Fourth of July party in 2016.
“Look What You Made Me Do” music video (2017)
Look what we made her wear. Swift made clear she wasn’t messing around when she debuted the video for Reputation‘s lead single, in which she kills off all her sparkling former selves (including at least five wearing outfits featured in this very list), while the cool new Taylor wears black shorts and a black sweatshirt over a fishnet bodysuit — and, of course, dark red lips.
Reputation tour (2018)
Dark New Taylor was the star of the Reputation tour, and she brought the aesthetic introduced in “Look What You Made Me Do” (and an accompanying snake motif) to the stage with this glittering, single-sleeved black leotard.
Reputation tour (2018)
Grim as much of the Reputation era was, however, Swift hinted at a light at the end of the tunnel, performing part of the tour show in this rainbow romper (which also brought back the showwoman beading she’s always embraced onstage). Still, nothing could have fully prepared us for the sartorial pendulum swing that came next…
2018 American Music Awards
Swift began to move toward a new era when she attended the AMAs in 2018, looking like a human disco ball on the carpet in a mirrored Balmain minidress and thigh-high boots.
2019 iHeartRadio Music Awards
The Reputation tour’s hint of rainbow sparkles notwithstanding, 2019 brought the swiftest (ha), most radical style switch of Swift’s career when she threw out her burgundy lips and black bodysuits for a candy-colored fashion fantasy. Consistently hinting at the new color scheme on Instagram, Swift officially debuted the new look at the iHeartRadio Music Awards, wearing a Rosa Bloom romper covered in iridescent paillettes and butterfly heels.
2019 TIME 100 gala
Swift attended the 2019 TIME 100 Gala, where she was one of the magazine’s honorees, in a throwback look that was also totally new. Her pale pink and yellow gown by J. Mendel alluded to her fairy-tale style origins, but the sugary palette and impractical sleeves suggest a greater sense of irony and self-awareness about the whole bubblegum princess aesthetic. She’s wearing a heart-shaped ring, for crying out loud!
“Me!” music video (2019)
Over the course of the music video for Lover‘s first single, “Me!,” Swift dances through a pastel-rainbow fantasyland in seven different outfits (including ’50s- and ’60s-inspired dresses that speak to her retro sensibilities), many of which coordinate with her collaborator Brendon Urie‘s colorful wardrobe. These Candyland-esque uniforms echo some of Swift’s former stagewear, and her rose-tinted hair, which also changes elsewhere in the clip, reflects the pink-tipped new ‘do she wore to unveil the video — and, with it, a new musical era.
2019 Billboard Music Awards
Soon after dropping “Me!,” Swift opened the 2019 BBMAs with the song, marking her first live performance of the Lover era. On the carpet, she wore an elaborately ruffled lilac minidress; for the album’s onstage debut, the singer’s new penchant for pastel sparkles was on full display with this single-sleeved, fringed leotard.
“You Need to Calm Down” music video (2019)
The second single off Lover was Swift’s most political yet, a rainbow-colored statement of allyship. The music video, which features over 20 celebrities (most of whom identify as LGBTQ), takes place in the world’s most vibrant trailer park, which Swift struts through in a hot pink fuzzy coat, then a starry shirt tied at her waist. Most memorable of all, however, is the French fry costume that she wears to a food fight where she meets up with Katy Perry, dressed as a hamburger. Their moment of fast-food sisterhood made headlines, as it ended a years-long feud (which reportedly inspired another Swift single with cameo-filled video) between the singers.
2019 Teen Choice Awards
To accept the first-ever Teen Choice Icon Award, Swift intensified Lover‘s rainbow palette in a patterned Versace bodysuit and shorts under a matching blazer.
2020 Sundance Film Festival
Promoting her documentary, Taylor Swift: Miss Americana (2020), at the 2020 Sundance Film Festival, Swift was dipped head to toe in houndstooth plaid for this sleek Carmen March look. —James Mercadante
For her first surprise album Folklore, Swift sported a striped rugby shirt, plaid pants, and lace-up shoes that perfectly encapsulated her eighth album era. —J.M.
2020 cover of Entertainment Weekly’s “Entertainers of the Year” issue
Reuniting with Folklore photographer Beth Garrabrant, Swift brought back her signature red lips with a red dress to match, plaid tights, and a brown sherpa jacket. —J.M.
2021 Grammy Awards
Before winning the 2021 Grammy award for Album of the Year for Folklore — making history as the first female artist to win the award three times — Swift strutted the red carpet in a floral Oscar de la Renta dress. —J.M.
All Too Well: The Short Film New York premiere
During the premiere of her short musical film for the 10-minute version of “All Too Well,” the singer-songwriter abandoned her red lipstick for a light pink shade while arrayed in a violet velvet suit. —J.M.
2022 MTV VMAs
Accepting MTV’s VMA for Video of the Year for “All Too Well,” Swift announced her 10th studio album, Midnights, in a silver crystal naked dress, designed by Oscar de la Renta. —J.M.
2023 Grammy Awards
Swift brought back her now-well-established crop top look at the 2023 Grammys, with this midnight-blue Roberto Cavalli ensemble that suited her ongoing Midnights era. Plus, can we talk about those statement earrings by Lorraine Schwartz? —Kevin Jacobsen
The Eras Tour (2023)
Swift got out the Bedazzler for this rhinestone bodysuit with matching boots on her record-breaking Eras Tour, debuting this look at her first stop in Arizona. —K.J.