The Full Transformation Of Taylor Swift From Country Singer To Chiefs WAG

Taylor Swift's most recent looks on the sidelines of Chiefs' games are a long way off from the flirty sundresses and cowboy boots she wore in the early 2000s. "I would describe my own style as being something that's sort of ever-changing but based in a very feminine kind of vibe," Taylor Swift told Extra in 2015. And we couldn't have put it better ourselves. Swift has gone from the ultimate country cutie, to sparkly superstar, to fashion-forward WAG, and pretty much everything in between. But even though her clothing choices are constantly evolving, there's still always an air of familiarity in her looks.

No matter how her wardrobe has changed, Swift has always retained her authenticity. She has expertly used fashion to express her innermost thoughts and feelings, immersing fans in her highly personal albums and bringing them more intimately into her world. And her carefully thought-out style transformation has been quite the sight to behold.

When teenage Taylor Swift burst onto the scene, she was determined to make it big in country music — and she dressed the part with a penchant for strappy summer dresses and cowboy boots, serving up a down-home, Americana vibe. For the CMT Music Awards in May 2006, the country cutie went full Southern belle in a flowy white dress with black detailing around her waist and matching T-bar pointed toe heels. The look may not have been the trendiest, but it proved she paid attention to style, which would serve her well as she developed into a global fashion icon. 

That same month, Swift wore her favorite footwear on the red carpet — cowboy boots! The star showed her small-town charm at the ACM awards with traditional, brown leather-look boots and a flowy sundress with mixed patterns. It fit her fresh-off-the-farm vibe, but, nodding to things to come, her oversized hoop earrings  were fun, youthful, and glam.

The dress-and-cowboy-boot combo became such a hit with fans that countless OG Swifties emulated her style, including her stunning natural curls, at Swift's shows. But trendsetting wasn't her intention. "I wasn't trying to make people dress a certain way, but seeing girls coming to my shows wearing sundresses and cowboy boots and curling their hair is one of my favorite experiences ever because I remember when I was weird for dressing the way that I dressed," she told Marie Claire.

By 2008, Taylor Swift was a bona fide country superstar. Her "Fearless"-era style was a lot sparklier than her debut fashion, as she embraced more glamor and fewer cowboy boots. That May, she made the whole place shimmer in a head-to-toe black and gold dress that positioned her as an up-and-coming fashion icon. The Badgley Mischka Met Gala gown marked a transition from flowy day dresses to more structured, designer numbers. Her curls became more polished and defined too, just like her aesthetic. The look was very in keeping with the enchanting theme of "Fearless," as Swift looked like the princess she sang about in "Love Story." 

For the 2008 Grammy Awards, Swift tapped into a romantic aesthetic in a custom Sandi Spika purple corset dress, but the 18-year-old was still wide-eyed and learning about the fashion game. "It has crystals and European fabric that I can't remember the name of. And I'm wearing Tiffany's jewelry that's totally worth more than my house," she told CBS on the red carpet. (Hey, you can take the girl out the country ...) 

But don't think this small town beauty had gone totally luxury label yet. She told Teen Vogue that November, "My favorite places to shop are Forever 21, I find the coolest things that you would never expect at Target and Walmart, I love shopping there."

In 2009, Taylor Swift strayed even further from her country girl style after a celeb-esque makeover. Following the huge crossover success of "Love Story," she wore chicer pieces more aligned with her new, glam persona. We also started to see Swift's standout pout that would become her signature at September's MTV Video Music Awards. Makeup artist Gucci Westman gave her a taste of the red lip during her Allure photoshoot that year — despite her mom being against it. 

"[Andrea Swift] was like, 'Well, Taylor doesn't wear red,'" Westman said on Today. Thankfully, the makeup genius got her way, and Swift liked the lipstick so much she even took home a tube from Westman. At the CMA Awards later that year, Swift kept romantic glitz alive in a more sophisticated way, with a strapless, tulle-skirt dress from Reem Acra. The fit-for-a-princess ensemble was perfect for the era and her personality, and the gold and champagne shades teased a more grown-up Swift as she left her teen years behind.

Asked by Seventeen to describe her 2009 wardrobe in a single word, she answered, "experimental." Swift hadn't completely lost her connection to her old self though, because she still loved a classic sundress. "It's always a sundress for me. That's my go-to outfit. I have, probably, over 100 sundresses," she said.

Taylor Swift was firmly on the red lipstick train by 2010 — the year she released her third album, "Speak Now" — and she embraced elegant, classic, and feminine fashion. In January 2010, Swift brought sparkle to the Grammy Awards in a midnight blue, off-the-shoulder Kaufmanfranco ensemble. The dress was custom and proved she was ready to try new more mature silhouettes, cuts, and darker colors. She also leaned into a more retro aesthetic with her pinned-up curls and lipstick.

Swift showed her 1950s-inspired vibe with a modern twist when she wowed in a sunny, bright yellow skater dress with double straps for the Country Music Hall of Fame's "All For The Hall" Benefit. She added matching satin, peep-toe, black and yellow pumps featuring an adorable bow, while making it clear she wasn't ready to give up her staple garment. 

"There's just something so feminine about a dress. Whether it's a summertime dress that makes me feel carefree, an evening cocktail dress that makes me feel fancy, or a vintage dress that makes me feel like a '50s housewife — which I enjoy feeling like, for some reason — I just really like dresses," she told Harper's Bazaar.

In 2012, we noticed a sizable shift in what Taylor Swift wore. She still preferred feminine silhouettes and dresses, but her "Red" era was more synonymous with fitted shorts, graphic tees, and bowler hats. The star also ditched her natural curls at times, instead opting for softer waves or straight locks. 

It seemed her decision to stray from dresses (though not completely) was as intentional as her transition from country to pop. "I think doing something that's different, that's out of your comfort zone, is important. Personal growth, let's call it that," she told Harper's Bazaar of her transformation, as she made the rare choice to wear pants during a photoshoot.

And try something different, she did. Having previously performed predominantly in dresses, the star stunned in black bedazzled shorts and a semi-sheer nude top for the iHeartRadio Music Festival in September 2012. A month later, she slipped into a very similar look for the BBC Radio 1 Teen Awards to anchor the aesthetic. Swift wore sported shimmery light green bottoms, a see-through black embellished top, and flat black shoes with a bow.

Taylor Swift's 2012 clothing choices were a soft transition into her 2014 aesthetic, when she wore more grown-up outfits that gave off an "It Girl" vibe. Swift dressed more fashionably without relying on fads and trends, and told Glamour her style had developed so much she regretted some of her earlier looks. "I play the tape of my life forward and don't wear the things that my kids or grandkids will make fun of me for wearing, [like] 'Wow, cool, Mom, cool cowboy boots that you were wearing constantly in 2006!'" she said. The star also told KISS about her new mantra, "I try to stick to things that I don't think I'll be embarrassed by in 20 years."

In 2014, the superstar ditched country music completely to create the 100% pop album "1989." It featured coming-of-age songs, including tracks inspired by her move from Nashville to New York City – and her clothing reflected those big life changes. Her transition from girl to woman (she was 25 at the time) was demonstrated with a stunning black and pink Carolina Herrera strapless dress for the Golden Globes. She showed her elegant and classy side again a few months later at the Met Gala in a light pink gown by Oscar de la Renta, with a long train and delicate silver embellishments. "Never Grow Up?" More like totally grown-up.

Three years later, the dark and thematic "Reputation" era was brewing, and Taylor Swift gave us hints through her clothing. Her style developed in a modern, cosmopolitan way as she wore chicer, more fashionable pieces. That included her Vanity Fair Oscar Party dress that was one of her most stylish and mature ensembles ever. The Alexandre Vauthier couture gown featured a daring, plunging neckline and a high slit that confirmed she'd come a long way since her sundress and boots days. The uber modern look was accented in a glam yet tasteful way via her strappy gold heels, metallic clutch, and statement choker.

A grungier aesthetic also emerged in 2016, as she wore a lot of dark colors and flipped between a chic, straight blonde bob and unkempt curls. As "Reputation" grew closer, she attended the Met Gala in an avant-garde dress that shocked the world. Gone were her floral, delicate dresses, replaced by out-there, bold pieces. Swift wore a custom Louis Vuitton dress with a black and silver snakeskin pattern and cut-outs across her torso. She anchored the dark and moody theme with a bleach blond shaggy bob, dark lipstick, maroon nail varnish, and criss-cross, knee-high heels. The outfit got some mixed responses, but ushered in a new, much edgier era for the star.

Taylor Swift moved even further away from her cute, feminine dresses in 2017. The star was going through a turbulent time amid her drama with Kanye West and her sexual assault case against a radio DJ, and shunned interviews to promote her new album. As she wrote on Instagram, "There will be no further explanation. There will just be reputation." Swift's outfits mirrored how she felt. As her "Reputation" era took full hold, her wardrobe was full of super dark, edgy pieces.

Embellished black was her "End Game" during a 2017 concert in Houston. Swift wore a fringed black mini skirt with a sheer, black, patterned long sleeve top over a bandeau crop top. The glitter and a darker red lip proved the sparkle-loving teen was still in there somewhere, though. Swift's "Reputation Tour" wardrobe featured lots of black with feisty, knee-high boots, including a hooded number over a sparkly bodysuit.

Speaking about the dramatic wardrobe change, she told Vogue, "This is the character you created for me, let me just hide behind it." She added, "I never wanted to tear down my house. 'Cause I built this house. This house being, metaphorically, my body of work, my songwriting, my music, my catalog, my library. I just wanted to redecorate."

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

After the dark clouds of "Reputation" disappeared, the snakes dispersed and the butterflies fluttered in. Taylor Swift was very much in love in 2019, and it showed in her clothes. For her "Lover"-era, classic Swift returned in an even more sparkly, overtly feminine way than before. Her looks were filled with rhinestones, hearts, and pastel shades, and her harsh "Reputation" outfits were replaced with ethereal dresses.

Swift attended the 2019 Time 100 Gala in a peach and yellow J. Mendel dress. The romantic vibes in her personal life were mirrored in its flowy fabric, floral detailing, and off-the-shoulder sleeves. Her makeup was much softer too, as she made a rare move to ditch red lipstick for light pink. For the Billboard Music Awards that yer, she proved the uber girlie, "Enchanted"-belting Swift was very much back in a pink, silver, and gold sequined one-shoulder bodysuit with silver ankle boots. The star showed how important fashion was to the era by launching a collection inspired by the music with Stella McCartney.

Taylor Swift released "Folklore" in 2020, which marked one of her most stripped-back albums to date. But this was one of the first times her clothing didn't match the aesthetic of her latest album. "Folklore" and "Evermore" were more understated and folksy than her previous releases, with a mythical, autumnal, and even witchy aesthetic. But Swift's outfits at the time were much more structured and corporate-inspired.

Swift rocked a black-and-white plaid ensemble at the Sundance Film Festival in January 2020. The cut of the strapless jumpsuit and matching structured coat screamed powerful woman. At the NME Awards the following month, she stunned in a pinstripe suit inspired look, made up of a slouchy shirt and blazer combo with matching shorts and white, pointed-toe boot heels that gave us "The Man" vibes. 

"Folklore" and "Evermore" were inspired more by Swift's imagination than her personal life, which may explain why her clothing didn't match her album aesthetic so closely. The music was also released amid Covid-19 restrictions, when Swift dressed herself. "[She took] an incredible amount of creative control over her image ... in the 'Folklore' and 'Evermore' era when, due to the circumstances of the pandemic, she self-styled," Sarah Chapelle, author of "Taylor Swift Style," told Billboard.

As Taylor Swift headed into her mid-30s, she debuted a sexier style in 2022 amid the release of "Midnights." The album delved into more grown-up themes surrounding love and sex (perfect for a Swiftie hook-up playlist), which was reflected in her more daring outfits.

The 2022 VMAs brought out one of her most glamorous and seductive get-ups ever. The stunningly glamorous, backless Oscar de la Renta mini-dress featured nude mesh that gave the illusion she was only wearing draped strings of silver jewels. Swift wore the dress with matching Christian Louboutin heels that made her impossibly long legs look even longer, and, coupled with her red lips, gave Old Hollywood glamour vibes.

Later in the year, she served the same aesthetic but with a more modern twist. She slipped into a David Koma dress that was essentially a strappy, black bodysuit with a jewel, mesh skirt for the MTV Europe Music Awards. Dressing for revenge? Maybe. Dressing for the sexy, fulfilled, and strong woman she is? Definitely.

Taylor Swift underwent another clothing transformation in 2023 when she started dating NFL star Travis Kelce. She wore sportier outfits, regularly attending games in Kansas City Chiefs merch. That October, she watched alongside her WAG bestie Brittany Mahomes in a bright red sweatshirt emblazoned with the NFL team's logo (and matching red lipstick, of course). That same month, she took in a game alongside Kelce's mom wearing a sleeveless black top and a Chiefs jacket.

Swift took on a supportive role with her clothing rather than dressing as the main attraction as she had for most of her life. And there's nothing wrong with that. "Once you're in a budding relationship, your fashion choices change due to mutual influence, subconscious attraction, and a longing desire to impress the one you love," Peter Martinez, co-founder and fashion designer at Leather Skin Shop, exclusively told Women. 

Swift made it clear she wouldn't apologize for championing her man, either. "When you say a relationship is public, that means I'm going to see him do what he loves, we're showing up for each other, other people are there and we don't care," she told Time.

As Taylor Swift's relationship with Travis Kelce developed, so did her style. Swift's Chiefs game outfits became more WAG glam and fashion-forward in 2024, the same year she dropped the album "The Tortured Poets Department." In September, Swift attended a game in trending all-denim, with a corset top and high-waisted shorts she accessorized with super sexy maroon, knee-high boots. The look suggested Swift had become more comfortable in all aspects of her life as she focused on fashion and trends again, but in a more understated way that didn't distract from her man.

That same month, she hit the MTV Video Music Awards red carpet in an outside-the-box green and yellow plaid Versace number. The corset dress fit her body like a glove, and she added strappy, leather-look, bicep high gloves with thigh-high black boots for edge. The ensemble seemed to be an amalgamation of her past eras, which was fitting for the hugely successful Eras Tour she was on at the time. As Sarah Chapelle told Billboard, "She still retains this semblance of recognizability, and I think that that's one thing that she does incredibly well in all aspects of her branding and her fashion."