Photo: Christopher Polk/Penske Media via Getty Images
Taylor Swift is the master of “Easter eggs,” subtle clues she’ll drop here and there that provide hints to her work and life. And one of her favorite ways to do so is through her clothing. It’s her unique way of communicating with her fans, and she’s become notorious for it. Is it a good thing? Is it a bad thing? Well, our fashion critic, Cathy Horyn, thinks it’s a bit of both.
Since her early, sideswept-bang, natural-curl, cowboy-boot-wearing days, the singer has had a distinct approach to dressing that, for all intents and purposes, mimics something a regular-degular person might do: be inconsistent. Depending on her phase of life or whatever might be in trend at the time, Swift has been unafraid to make a gradual (okay, sometimes abrupt) shift in whatever she’s wearing. For example, anything and everything twee (think beanies, plaid skirts, high socks, oxfords) was Swift’s bread and butter for years, so much so that it felt like she practically owned the aesthetic. That is, until she traded in her knit stockings for a blunt bob, bright two-piece sets, and a much edgier, bolder way of dressing at the 2016 Grammys and Met Gala. C’est la vie! Trends change! People change! And Swift is no different. Here, we take a look at her style evolution throughout the years. I mean, she’s now a billionaire, after all, and sometimes she dresses like it.
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The singer wore a custom Vivienne Westwood look to kick off the global leg of her Eras tour on May 9, 2024. This dress has one of her lyrics, “I love ... The singer wore a custom Vivienne Westwood look to kick off the global leg of her Eras tour on May 9, 2024. This dress has one of her lyrics, “I love you, it’s ruining my life,” scribbled all over it. If there’s one thing this songwriter loves, it’s a self-reference. Photo: John Shearer/TAS24/Getty Images for TAS Rights Management
On February 11, 2024, Swift grabbed her ever-infamous girl gang and took the squad to the Super Bowl to support her boyfriend, Kansas City Chiefs tigh... On February 11, 2024, Swift grabbed her ever-infamous girl gang and took the squad to the Super Bowl to support her boyfriend, Kansas City Chiefs tight end Travis Kelce. The singer wore a pair of Area jeans. A big win that night for the Chiefs and brand awareness all around. Photo: Ellen Schmidt/Las Vegas Review-Journal/Tribune News Service via Getty Images
Just a week before, she walked the red carpet at the Grammys in a very polarizing custom Schiaparelli haute couture look. She seized the night and, in... Just a week before, she walked the red carpet at the Grammys in a very polarizing custom Schiaparelli haute couture look. She seized the night and, in classic TayTay fashion, announced her next album onstage. Photo: Matt Winkelmeyer/Getty Images for The Recording Academy
Fans confused this slinky green Gucci dress as a potential Easter-egg clue, possibly hinting at a Reputation re-record, when Swift wore it to the Gold... Fans confused this slinky green Gucci dress as a potential Easter-egg clue, possibly hinting at a Reputation re-record, when Swift wore it to the Golden Globes on January 7, 2024. For once, the Swifties were wrong. Photo: Monica Schipper/GA/The Hollywood Reporter via Getty
Lucky number 13! Out in New York for her birthday (December 13, 2023, duh), Swift wore an embellished dress from Clio Peppiat. What is it with us Sagi... Lucky number 13! Out in New York for her birthday (December 13, 2023, duh), Swift wore an embellished dress from Clio Peppiat. What is it with us Sagittarius girls obsessing over celestial motifs? Photo: Gotham/GC Images
Women supporting women! In November 2023, Swift attended Beyoncé's Renaissance movie premiere in, of course, a silver Balmain gown. Beyoncé also atten... Women supporting women! In November 2023, Swift attended Beyoncé's Renaissance movie premiere in, of course, a silver Balmain gown. Beyoncé also attended Swift's tour-movie premiere earlier that year. Photo: Gareth Cattermole/WireImage for Parkwood
By golly, Swift is going to dress for fall if it’s the last thing she does. The singer was spotted out and about in New York City in October 2023 in a... By golly, Swift is going to dress for fall if it’s the last thing she does. The singer was spotted out and about in New York City in October 2023 in an oversize Stella McCartney rugby shirt and knee-high Prada boots. Photo: Gotham/GC Images
The singer, spotted here with Kelce in New York City on October 15, 2023, dares to ask: What better to wear on date night than a sheer Jean Paul Gault... The singer, spotted here with Kelce in New York City on October 15, 2023, dares to ask: What better to wear on date night than a sheer Jean Paul Gaultier shirt? Photo: Gotham/GC Images
A few days prior, Swift attended the premiere of Taylor Swift: The Eras Tour concert film on October 11, 2023, in a baby-blue Oscar de la Renta dress.... A few days prior, Swift attended the premiere of Taylor Swift: The Eras Tour concert film on October 11, 2023, in a baby-blue Oscar de la Renta dress. Busy week. Photo: Matt Winkelmeyer/Getty Images
The laugh heard round the world. On September 24, 2023, Swift and Kelce hard-launched their relationship, sending the sports and pop-culture worlds bu... The laugh heard round the world. On September 24, 2023, Swift and Kelce hard-launched their relationship, sending the sports and pop-culture worlds buzzing, when the singer was spotted in a suite at a Chiefs game repping slouchy gear from the team. Photo: David Eulitt/Getty Images
On September 12, 2023, Swift attended the MTV VMAs in a Versace look that I’m still sitting with. Photo: Udo Salters/Patrick McMullan via Getty Image
Quick! Millions of eyeballs are on you for the opening night of your sold-out tour, who are you wearing? Versace? Good answer. Swift had the same one ... Quick! Millions of eyeballs are on you for the opening night of your sold-out tour, who are you wearing? Versace? Good answer. Swift had the same one when she kicked off her U.S. tour in March 2023. Photo: Christopher Polk/Penske Media via Getty Images
Speaking of eras, Swift was in her Midnights era when she wore this deep-blue Roberto Cavalli set to the 2023 Grammys on February 5. She also happens ... Speaking of eras, Swift was in her Midnights era when she wore this deep-blue Roberto Cavalli set to the 2023 Grammys on February 5. She also happens to be wearing $3 million worth of jewelry here. Same. Photo: Jeff Kravitz/FilmMagic
The singer wore this look, designed by David Koma, to the MTV Europe Music Awards on November 13, 2022. Photo: Henning Kaiser/dpa/picture alliance via...The singer wore this look, designed by David Koma, to the MTV Europe Music Awards on November 13, 2022. Photo: Henning Kaiser/dpa/picture alliance via Getty Images
Swift wore this stunning Oscar de la Renta look, dripping in jewels, to the MTV VMAs on August 28, 2022. She really is a Mirrorball. Photo: Arturo Ho...Swift wore this stunning Oscar de la Renta look, dripping in jewels, to the MTV VMAs on August 28, 2022. She really is a Mirrorball. Photo: Arturo Holmes/FilmMagic
Everyone remembers where they were when the “All Too Well” ten-minute music video dropped. Swift herself was at the premiere of the short film on Nove... Everyone remembers where they were when the “All Too Well” ten-minute music video dropped. Swift herself was at the premiere of the short film on November 12, 2021, wearing this velvet suit. Nothing says “I’m the director” like a pantsuit. Photo: ANGELA WEISS/AFP via Getty Images
Florals? For spring? Groundbreaking. At least when Swift does it. The singer wore this Oscar de la Renta dress to the Grammys on March 14, 2021, where... Florals? For spring? Groundbreaking. At least when Swift does it. The singer wore this Oscar de la Renta dress to the Grammys on March 14, 2021, where my favorite album of hers, Folklore, was up for several nominations. Photo: Kevin Mazur/Getty Images for The Recording Academy
This Etro dress she wore to the Golden Globes on January 5, 2020, is definitely a dress! That’s all I have to say about that! Photo: Steve Granitz/Wir...This Etro dress she wore to the Golden Globes on January 5, 2020, is definitely a dress! That’s all I have to say about that! Photo: Steve Granitz/WireImage
Remember the movie Cats? It truly feels like a fever dream. Swift, who starred in the film, wore this floral Oscar de la Renta frock to the premiere o... Remember the movie Cats? It truly feels like a fever dream. Swift, who starred in the film, wore this floral Oscar de la Renta frock to the premiere on December 16, 2019. Photo: ANGELA WEISS/AFP via Getty Images
Swift wore this Versace blazer and Christian Louboutin crystal-embellished over-the-knee boots on August 26, 2019, to the MTV VMAs. In the best way po... Swift wore this Versace blazer and Christian Louboutin crystal-embellished over-the-knee boots on August 26, 2019, to the MTV VMAs. In the best way possible, this is a look my favorite art teacher would have killed to wear. Photo: Dimitrios Kambouris/Getty Images
Platinum blonde TayTay! The singer wore this Louis Vuitton look to co-chair the 2016 Met Gala. The theme was “Manus x Machina.” Photo: George Pimentel...Platinum blonde TayTay! The singer wore this Louis Vuitton look to co-chair the 2016 Met Gala. The theme was “Manus x Machina.” Photo: George Pimentel/WireImage
Now we’re talking. This bob means business! The singer wore this sleek Alexandre Vauthier haute couture dress to the 2016 Vanity Fair Oscars after-par... Now we’re talking. This bob means business! The singer wore this sleek Alexandre Vauthier haute couture dress to the 2016 Vanity Fair Oscars after-party. Photo: John Shearer/Getty Images
Swift went through a phase where she loved a two-piece look. This pink and red one, by Versace, carried her down the red carpet at the 2016 Grammys, a... Swift went through a phase where she loved a two-piece look. This pink and red one, by Versace, carried her down the red carpet at the 2016 Grammys, and all the way up onto the stage when she won Album of the Year, making her the first woman to win the award twice. Photo: Steve Granitz/WireImage
The singer brought out the Old Hollywood glam in this Oscar de la Renta pink satin gown at the 2014 Met Gala. Photo: Dimitrios Kambouris/Getty Images
The twee queen strikes again! Swift was spotted in New York City on December 22, 2014, in the quintessential 2014 outfit. I just know this look was on... The twee queen strikes again! Swift was spotted in New York City on December 22, 2014, in the quintessential 2014 outfit. I just know this look was on so many mood boards back in the day — the slouchy beanie, the plaid skirt, the colored tights, and heeled oxfords. Photo: James Devaney/GC Images
The singer really can serve up the nostalgic glamour. She sported a finger-wave bob and a Hervé Léger by Max Azria dress to the 2013 MTV VMAs. Photo: ...The singer really can serve up the nostalgic glamour. She sported a finger-wave bob and a Hervé Léger by Max Azria dress to the 2013 MTV VMAs. Photo: Dimitrios Kambouris/WireImage
Okay, Bond girl! This sleek look by Elie Saab at the 2013 Brit Awards works for me. Photo: Eamonn M. McCormack/Getty Images
Ah, the 2009 VMAs. Swift wore this dazzling one-shoulder Kaufman Franco gown on the red carpet, only to later have her acceptance speech rudely interr... Ah, the 2009 VMAs. Swift wore this dazzling one-shoulder Kaufman Franco gown on the red carpet, only to later have her acceptance speech rudely interrupted by a musician who shall not be named. Photo: Stephen Lovekin/FilmMagic
I’m a sucker for even a bit of corseting, and this dress Swift wore to the 2008 Grammys (her first ever!) makes me swoon a little. It’s sweet! Photo: ...I’m a sucker for even a bit of corseting, and this dress Swift wore to the 2008 Grammys (her first ever!) makes me swoon a little. It’s sweet! Photo: Frazer Harrison/Getty Images
Baby's first Met Gala! Swift wore this bedazzled Badgley Mischka and her (at the time) signature curls on the red carpet on May 5, 2008. Photo: Stephe...Baby's first Met Gala! Swift wore this bedazzled Badgley Mischka and her (at the time) signature curls on the red carpet on May 5, 2008. Photo: Stephen Lovekin/Getty Images
Another princess-y Swift look for good measure, spotted here in a customs Sandi Spika Borchetta dress (she also designed the singer’s look for the “Lo... Another princess-y Swift look for good measure, spotted here in a customs Sandi Spika Borchetta dress (she also designed the singer’s look for the “Love Story” music video). This outfit has lore. Sandi is the wife of Scott Borchetta, the founder of Big Machine Label Group, whose first signed talent was Swift herself. Scott later sold the masters for Swift’s first six albums to Scooter Braun, who reportedly refused to sell them back to Swift. Instead of accepting defeat, the singer simply rerecorded her work, and now we’ve got a litany of “Taylor’s Version” albums to play back instead. Photo: Michael Buckner/Getty Images
This is how I first remember Swift: an empire-waist dress, cowboy boots, and some natural-looking curls. She’s seen here at the 2006 Academy of Countr... This is how I first remember Swift: an empire-waist dress, cowboy boots, and some natural-looking curls. She’s seen here at the 2006 Academy of Country Music Awards. Photo: Michael Buckner/Getty Images
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