Long Live Taylor Swift's Best Outfits of All Time

Narrowing down Taylor Swift's best outfits is, I imagine, a little like choosing her Eras Tour setlist. There's a catalog hundreds-deep to choose from; every fan has their favorites and passionately-debated rankings. And when it's all put together, it tells the story of a genre-bending, record-shattering career.

Swift, a natural-born storyteller, approaches her wardrobe in chapters. Every Taylor Swift era, onstage and off, has a distinct aesthetic. Her debut country album came with cowboy boots and princess dresses fit for a Nashville prom. When she pivoted to top ten pop with 1989, her tops became cropped and her Christian Louboutin heels grew several inches. By the time she entered her Life of a Showgirl style era in 2025, Swift and her stylist, Joseph Cassell Falconer, had curated a two-toned approach: glitzy Bob Mackie, Roberto Cavalli, and Area costumes for the album artwork and music videos; down-to-earth winter coats and knee-high boots for "real life" beyond the curtain.

But style isn't all about the external narrative for Swift. Like her lyrics, her best looks are almost diaristic. “Going through different phases is one of my favorite things about fashion," Swift said in her 2016 Vogue cover story. "I love how it can mark the passage of time. It’s similar to my songs in that way—it all helps identify where I was at in different points of my life."

Taylor Swift's best outfits also have a tendency to send a message. Take her powerful shirt emblazoned with her first six album titles at the 2019 American Music Awards, amid the dispute over buying back her masters. Even her casual outfits have something to say: Whether she's walking a red carpet, sitting down on a Late Night talk show, or joining fiancé Travis Kelce for a New York City date, Taylor Swift tends to prioritize women-led brands and independent businesses alongside her favorite runway labels like Louis Vuitton, Gucci, and Vivienne Westwood.

With her new documentary, The End of an Era, streaming now, and her 36th birthday arriving on December 13, there's never been a better time to revisit Taylor Swift's best outfits across every era, event, and appearance. These looks are a real style legacy to leave.

Taylor Swift's Best Outfits: Red Carpet Looks

The Grammys. The Golden Globes. The Billboard Music Awards. The American Music Awards. The iHeartRadio Music Awards. If there's a ceremony where the biggest names in songwriting and performing are honored, Taylor Swift is on the guest list—and setting records along the way. She attended her first Grammy awards in 2009; a year later, she was carting home her first three trophies and being named the then-youngest Album of the Year winner in history. By 2025, she'd amassed 14 Grammys, 49 Billboard Music Awards, and 40 American Music Awards. (The latter two are the most wins for any artist.) With every RSVP "Yes" she made, she added a memorable red carpet look to her catalog.

Taylor Swift's best outfits on the step-and-repeat are all styled by Joseph Cassell Falconer. He's worked closely with Swift to translate her sonic eras into sweeping ballgowns and spicy sequin mini dresses, depending on the album she's promoting. Over the years, a few designers have remained consistent in her red carpet rotation, like Oscar de la Renta and Versace. As her sound has matured, she's also explored more directional looks by Vivienne Westwood, Gucci, and Miu Miu.

Swift's red carpet outfits get rarer by the year. (For example, she hasn't attended the Met Gala since co-chairing in 2016.) When she does appear, she dresses to win.

Taylor Swift at the 67th Annual Grammy Awards (2025)

At the 2025 Grammys, Taylor Swift set aside the black and white palette of her moody eleventh album, The Tortured Poets Department, for a burning red corset mini dress by Vivienne Westwood. Was it a hint at the sequins and shimmer to come in The Life of a Showgirl? Or, a tribute to her fiancé, Travis Kelce, in that shade of Kansas City Chiefs red? Swift didn't comment on her styling for the night, but she did pull double-duty as a jewelry designer. With help from her favored red carpet jeweler Lorraine Schwartz, Swift created a ruby leg chain set with a "T" charm. Fans speculated it was a reference to the lyrics of "Guilty as Sin"; onlookers all confirmed it was one of her best red carpet looks to date.

Taylor Swift at the Golden Globes (2024)

Taylor Swift's Eras Tour concert film didn't ultimately win her 2024 Golden Globes nomination for Cinematic and Box Office Achievement. She did, however, win the night's best-dressed list in this custom Gucci gown. Floor-length green sequins and a caged open back were a glamorous contrast to the scaled-back ballgowns she'd worn in previous years. And those DeBeers diamond earrings? They hit all the right notes—and became a staple everywhere from her 35th birthday party to future red carpets.

Taylor Swift at the MTV VMAs (2022)

Even the on-stage reveal that Taylor Swift had secretly recorded her tenth album, Midnights, couldn't completely outshine her 2022 MTV VMAs dress. The singer teased at a "Bejeweled" era ahead with an Oscar de la Renta mini dress comprised of looped and tangled crystal chains. Some fans had also interpreted the look as a callback to Swift's diamond-filled bathtub in the "Look What You Made Me Do" music video, but, alas—this was a forward-facing outfit in the end.

Taylor Swift at the "All Too Well" short film premiere (2021)

Taylor Swift announced she had entered her director era with a press tour for her "All Too Well" short film in 2021. At the official New York City premiere, she arrived in a wardrobe curveball: a two-piece suit by Etro. Normally, Swift prefers dresses to tailored separates on the red carpet. But this double-breasted blazer and matching trousers still felt packed with personality, thanks to the rich purple-burgundy velvet and accompanying soft up-do.

Taylor Swift at the BRIT Awards (2021)

Taylor Swift's 1989-era penchant for crop tops and matching sets returned years later on the 2021 BRIT Awards red carpet. This time, the formula was all grown up in the form of a beaded Miu Miu bustier and floor-length column skirt. Blooming silver flowers coated both pieces, amplifying the shimmer of jewelry by Jessica McCormack, Tiffany & Co., Sophie Bille Brahe, and Ananya.

Taylor Swift at the 63rd Annual Grammy Awards (2021)

Taylor Swift chose this blossoming Oscar de la Renta mini dress for the 2021 Grammy Awards. It just as easily could have accompanied a trip to "The Lakes," as in Folklore's bonus track. The assemblage of 3-D florals evoked the cozy, off-the-grid aura of her album, while Christian Louboutin lace-up heels and Cathy Waterman jewelry filled the classic red carpet quotient. Forget going to "touch grass": This best-dressed entry makes me want to pick flowers.

Taylor Swift at the 'Vanity Fair' Oscar Party (2016)

In a CBS Mornings interview, Taylor Swift said she is not naturally "sexy, edgy, or cool." Yet all three of those words could apply to her 2016 turn on the Oscars party red carpet, when she slipped into this Alexandre Vauthier dress. Between the ultra-plunging neckline and the mile-high slit, it might just be the one that inspired her "Dress"-dedicated track on Reputation.

Taylor Swift at the Grammys Red Carpet (2016)

Taylor Swift's second Album of the Year win came with her first Versace date to the Grammy awards. The two-tone skirt set marked a major departure from the gowns she'd worn for past ceremonies, and reflected the upbeat pop energy of 1989 to a T. Her only additions to the understated look? Lorraine Schwartz jewelry and Stuart Weitzman sandals.

Taylor Swift at the "Charles James: Beyond Fashion" Met Gala Red Carpet (2014)

Sometimes, the Met Gala red carpet is a place for A-list guests to get experimental. (More on that in a moment.) Other times, it's a place for stars to dress in their time-honored bests. Taylor Swift's 2014 turn up the Metropolitan Museum of Art's famed steps felt like the latter: a slight evolution of the polished, pristine gowns she'd already worn to several award shows and galas at this point in her career. Oscar de la Renta crafted a baby pink gown dusted with golden florals, culminating in a voluminous bow and bustle.

Taylor Swift at the "Punk: Chaos to Couture" Met Gala Red Carpet (2013)

J. Mendel designed dozens of Taylor Swift's red carpet looks over the years, but never one quite like her 2013 Met Gala gown. Embracing the anti-establishment energy of "Punk: Chaos to Couture," Swift set aside her princess-y ballgowns for a sleek black dress inlaid with lace-coated cut-outs. Lorraine Schwartz jewelry and gilded gold detailing along her shoulders added a militaristic-chic touch.

Taylor Swift at the 'Vanity Fair' Oscars Party (2011)

For her first turn on the Vanity Fair Oscars Party red carpet, a Speak Now-era Taylor Swift understood the assignment. She channeled the famous statuette in a gilded Zuhair Murad mini dress and Jimmy Choo accessories.

Was this the night Swift set her sights on eventually writing and directing an original screenplay? No one knows for sure, but she certainly dressed like a multi-hyphenate star.

Taylor Swift at the 52nd Annual Grammy Awards (2010)

You never forget your first Grammy awards win—or what you wore to accept the golden gramophone trophy. In 2010, Taylor Swift brought home three awards for Fearless, including Album of the Year. At the time, she was the youngest person to ever win the accolade.

Her gown for the night resembles the "distant diamond sky" on the Fearless deep cut "Untouchable." Kaufmanfranco, which would become one of the red carpet favorites in her early career, provided an off-the-shoulder gown with angular cups and a sweeping train. It's regal but also wouldn't look out of place at a prom—which is a perfect fit for a high schooler-turned country superstar.

Taylor Swift's Best Outfits: Performance Looks

Think of a Taylor Swift song, and you can probably imagine the outfit she wears to sing it. "22"'s "happy, free, confused, and lonely" chorus comes with a T-shirt that reads, "Not a lot going on at the moment." Drop-waist princess gowns accompany the dreamy swell of "Love Story." When a stadium sings "Shake It Off," Swift is at the center in a a bombastic beaded two-piece set made for, well, shaking.

The worlds Taylor Swift crafts in her songs always include a coordinating outfit, and her best ones have always materialized the mood in her lyrics. The Eras Tour allowed Swift a chance to revisit her personal fashion history, combining the visual motifs of her past albums with updated designer credits and more mature details. She also got to debut looks for tours that never happened—like the pandemic-canceled "Loverfest" in 2020. With more than 50 variations of her looks from the 149-stop tour, it'd be easy to limit her best performance looks to just the Eras Tour. But here, we're looking back on moments that made history before the record-breaking concert, too.

Taylor Swift performing 'Lover' tracks on the Eras Tour (2023 – 2025)

Every night on the Eras Tour, Taylor Swift rose out from underneath the stage in one of four Versace bodysuits and knee-high Christian Louboutin boots. The pailettes across the one-piece reflected the blue, orange, purple, and pink tones of sunset—the same color palette Swift once likened to her Lover album's soundscape.

On a 2025 stop by The Late Show with Stephen Colbert, Swift admitted it wasn't the most comfortable costume on her Eras Tour rack. But, she knew it would make an impact. "I was constantly in a lot of physical pain, but the moment I put this on I was like, 'This is poppin', I’m doing it,” she said.

She discussed the mood-boosting power of the Versace bodysuit again in her Eras Tour official book. "Something about the combination of that song and that Versace glittery bodysuit I get to wear can pull me out of any funk, fix any headache, heal sore muscles," Swift wrote.

Taylor Swift performing 'Reputation' tracks on the Eras Tour (2023 – 2025)

Attendees at the Eras Tour's first Miami show in 2024 will never forget when Taylor Swift started her Reputation set—and neither will fans who tuned in via livestream. After spending more than 120 shows in a single Roberto Cavalli Reputation outfit, the singer debuted a new version of the bodysuit. This time, the serpents circling her body came coated in gilded gold.

A few months later, Swift would put theories that this costume signaled a Reputation (Taylor's Version) release to rest: Turns out, she never finished re-recording the album. But the headline-making bodysuit lives on.

Taylor Swift performing 'Folklore' tracks on the Eras Tour (2023 – 2025)

Taylor Swift conceptualized her surprise indie-folk album, 2020's Folklore, as coming from a period of isolation, where she imagined herself in a cabin in the woods. Her costumes to perform songs like "August" and "Betty" for the very first time weren't of the homespun sort, however. Instead, she tapped Alberta Ferretti for a range of custom maxi dresses with flowing, floor-grazing skirts and floral cut-outs—evoking a woodland fairy more than a Walden Pond pioneer. In an interview with Marie Claire, the designer called working on these looks an "honor," allowing Swift to "move and express herself at best."

Taylor Swift performing 'Midnights' tracks on the Eras Tour (2023 – 2025)

When Taylor Swift says "Meet me at midnight," this Zuhair Murad bodysuit is the one that instantly springs to mind. Spangled in hundreds of crystals creating a crescent moon and dozens of stars, it's the best example of Swift looking "Bejeweled" while closing the Eras Tour each night. Custom boots by Christian Louboutin (who else?) tied the entire deep blue look together.

Taylor Swift performing at the 36th Annual Rock 'n Roll Hall of Fame Induction Ceremony (2021)

Taylor Swift's performance looks were few and far between at the start of the 2020s, given her Lover tour's cancellation and the downgrading of events due to the Covid-19 pandemic. When she finally returned onstage at the Rock n' Roll Hall of Fame Induction ceremony to honor Carole King, she did so in a look that became a fan-favorite. Her electric performance of "Will You Still Love Me Tomorrow?" came with a custom Sarah Regensburger lace bodysuit, Louis Vuitton boots, and later, a Saint Laurent blazer.

Taylor Swift performing at the American Music Awards (2019)

In 2025, Taylor Swift secured ownership of her masters—ensuring her life's work really does belong to her. Back in 2019, owning her catalog wasn't a guarantee. So Swift took her fight to the American Music Awards stage, covering up a sequin bodysuit with a shirt displaying the titles of her six stolen albums. The song she paired them with? Her gender-equity anthem, "The Man."

Taylor Swift performing on the 'Reputation' Stadium Tour (2018)

Reputation takes the crown for Taylor Swift's boldest transformation—sonically and visually. But on the accompanying stadium tour, she found a way to combine the tough, combative energy of her Gucci- and Balenciaga-ified new wardrobe with the vulnerability and softness of her best acoustic songs. During a stripped-down moment in the set, she changed into a custom Jessica Jones sequin bodysuit and oversize jacket, plus Christian Louboutin combat boots. When she picked up her guitar and started playing the night's surprise song, fans knew she wasn't as unrecognizable as the era made her seem.

Taylor Swift performing at the MTV VMAs (2014)

1989 was weeks away from breaking an album sales record when Taylor Swift performed the first lead single, "Shake It Off," at the 2014 MTV VMAs. No one knew exactly what her all-out pop era would look or sound like—and this icy two-piece set and Stephanie Sophia heels were a sign of the chart-topping energy to come. Swift hadn't often worn crop tops or all-over beading in her previous eras. But in 1989's heyday, hemlines got shorter and embellishments got brighter. This performance look made a first impression that would last all the way to the Roberto Cavalli re-interpretations on the Eras Tour.

Taylor Swift performing on the 'Red' Tour (2013)

The Red era came with a head-to-toe style refresh for Taylor Swift—including her now-staple bangs!—that joined her on the world tour. It's best encapsulated by the 3.1 Philip Lim button-down, custom Lanvin Oxfords, and Bleulab shorts she wore to pick up a coordinating electric guitar during the set. In this understated-but-commanding look, it's hard to imagine an indie record that's much cooler than hers.

Taylor Swift performing at the 54th Annual Grammy Awards (2012)

One of the most deliciously sharp songs in Taylor Swift's catalog is "Mean," a knee-slapping rebuke to critics who once said she "can't sing." Before taking home the award for Best Country Song at the 2012 Grammy Awards, she performed the Speak Now track in over-the-top yeehaw fashion: a faded floral dress paired to nothing but a side braid and run-down shoes, on a ramshackle porch set. By setting aside the glittery dresses of her tours and past performances, Swift made a point about the power of her own voice and the country music tradition she trained in. And, she got the last laugh when the song ultimately took home two trophies.

Taylor Swift performing on the 'Speak Now' Tour (2011)

Eric Winterling's custom purple halter dress became the defining piece on Swift's 2011 tour for Speak Now. The shade mimics the palette of her painted album color, while the 1950s neckline and flouncy skirt look fit for the wedding crashing storyline of the title track. Technically, she accessorized with Everlon diamond knot earrings and an Esqueleto Old Mine diamond ring. But the most important finishing touch to fans was the lucky "13" drawn on her hand.

Taylor Swift performing on the 'Fearless' Tour (2009)

The Naeem Khan fringe dress. The Everybody Fargo knee-high boots. The Swarovski crystal-coated guitar. This is the version of Taylor Swift who had her first big hits ("You Belong With Me," "Love Story") and embarked on her first headlining tour. It's country styling re-done for a pop spotlight, planting the seeds for her crossover nearly a decade later.

Taylor Swift's Best Outfits: Street Style Looks

Taylor Swift's best street style outfits were the hardest to narrow down. She's become increasingly private as her career has skyrocketed, and there are entire years where she wasn't photographed a single time. (Most notably, the stretch from late 2016 to late 2017 when she was working on Reputation.) As someone who's only seen when she wants to be seen, her street style takes on a deliberate air.

She also has a sense of humor about the way her street style has aged—for better and for worse. "I had a phase where, for the entirety of 2012, I dressed like a 1950s housewife," she joked in her 2022 NYU commencement speech. "But you know what? I was having fun. Trends and phases are fun."

The closer you look at her street style, the more through-lines you'll find. Swift follows patterns, repeating favorite silhouettes and proportions with a rotating cast of luxury designers and accessible, women-owned brands. She tends toward jewelry with a vintage or sentimental bent. And when she appears to really love something, she wears it more than once.

Taylor Swift heading to 'The Late Show' (2025)

All the pillars of Taylor Swift's seasonal street style—a cuddly, oversize coat, a plaid mini skirt, and a knee-high boot—were present and accounted for in this look ahead of a stop by The Late Show with Stephen Colbert. The labels sound like a fit for a bonus verse on "Wi$h Li$t" (Miu Miu, Christian Louboutin, Saint Laurent), but the reliable template could be copied into any fan's wardrobe.

Taylor Swift at Arrowhead Stadium (2024)

2024 was the year Taylor Swift took over the WAG-osphere. Every Kansas City Chiefs home game came with a dedicated tunnel walk—never mind that Swift wasn't actually competing on the field. Her Chiefs game-day wardrobe ranged from vintage fan gear to off-the-runway outfits by the likes of Chanel and Louis Vuitton. The ones fans loved most (and Marie Claire readers resonated with) landed somewhere in the middle, like this crimson Charlotte Simone Penny Lane coat styled like a dress. It allowed Swift to show her team spirit and her affinity for great winter outerwear. Win-win.

Taylor Swift's 34th Birthday Party (2023)

In true Sagittarius form, Taylor Swift's birthday outfits are usually some of her best. She saved her top street style moment of 2023 for last, styling a Clio Peppiat beaded mini dress with an Anine Bing faux fur jacket and Aquazzura platform heels, to ring in her 34th birthday. In a few months' time, this LBD would take on an even bigger meaning—as a potential wink at the moody aesthetic of The Tortured Poets Department, which would release in April 2024.

Taylor Swift in New York City (2023)

Whether she dined with then-boyfriend Travis Kelce or a squad of her close friends, Taylor Swift's dinners (and associated outfits) were the talk of the West Village in fall 2023. On this particular occasion, she showed her affinity for fashion's return to prep codes in a Stella McCartney rugby shirt-dress and Prada boots, before heading out to dinner with Blake Lively.

Taylor Swift at Electric Lady Studios (2023)

Visions of Taylor Swift in a Ralph Lauren wedding dress began here: a mid-Eras Tour stop at Electric Lady Studios, where she styled a white eyelet lace set by the designer. This look brings together a few of her favorite more affordable brands, including Mansur Gavriel (for bags), Catbird (for jewelry) and Ayede (for sandals). It's polished, but not overstyled—and just as romantic as her best ballads.

Taylor Swift at the Tribeca Film Festival (2022)

Taylor Swift resumed her director era at the 2022 Tribeca Film Festival in a tailored Max Mara pinstripe suit and Prada loafers—plus a stack of new rings and earrings by Vrai and Ettika. Usually, Swift's street style is full of ideas for casual weekend outfits; this one could be the blueprint for taking on the work week with confidence.

Taylor Swift in New York City (2016)

"Leopard print" and "Taylor Swift" don't often show up in the same sentence. But on the eve of her Reputation era—and the debut of an edgier look—the star showed up to Lorde's 2016 birthday party ready to show new spots.

Taylor Swift in New York City (2016)

Taylor Swift's Bleachella chapter didn't last long, but it was memorable. She teed up a dramatic 2016 Met Gala appearance with a stop by Anna Wintour's townhouse, matching the punk-rock energy of her bleached bob to a Louis Vuitton leather jacket and grunge paid dress.

Taylor Swift in New York City (2014)

From afar, Taylor Swift's outfit for brunch with Karlie Kloss (what a 1989 opener!) feels like eons ago. (Not eras.) The Miss Patina plaid coat and bow-topped headband sum up the retro energy of her country-pop crossover style. But look closer, and there's still a basis for 2025 Taylor Swift. Over a decade later, she still loves Christian Louboutin shoes and patterned tights.

Taylor Swift in New York City (2011)

As Taylor Swift closed her Speak Now chapter and began recording Red, her street style preferences turned in a mid-century vintage direction. From the colorblocking to the bow-topped Marc by Marc Jacobs flats, this was the uniform for a singer ready to "Begin Again." It also marked the start of another decades-long style relationship: Swift was styling a Ralph Lauren sweater before shopping at the label's then-West Village boutique. (Ralph Lauren, you'll recall, designed the dress Swift wore to announce her 2025 engagement to Travis Kelce.)

Taylor Swift in New York City (2010)

This isn't an outfit that's just about Taylor Swift's favorite fall pieces of the 2010s—though she'd return to derby shoes and peacoats throughout her Speak Now, Red, and 1989 street style. Red's "All Too Well" immortalized a scarf (and innocence) lost in a relationship. All signs point to the accessory in question—a striped Gucci scarf—appearing in this look, tucked beneath her blue peacoat.

Taylor Swift at Milan Fashion Week (2010)

By 2023, nearly half of Taylor Swift's Eras Tour costumes would hail from Roberto Cavalli. The relationship got started all the way back in 2010, when Swift attended her first (and only) Milan Fashion Week front row with the designer. She leaned all the way into the house's mid-aughts boho phase with a flouncy white blouse, two-layer ruffled skirt, and buckled suede boots.