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London’s Victoria and Albert Museum is currently displaying an exhibit called Songbook Trail that celebrates the star’s style, which some fashion critics have called “boring.”Gareth Cattermole/Getty Images

One of the most viral fashion moments this year didn’t come from a red-carpet premiere, the Grammys or the Oscars.

Instead, it can be traced to a significantly unfashionable event: the Super Bowl. Taylor Swift’s NFL championship simple look – a black crochet corset top paired with denim – led to more than 3.7 million posts across platforms, such as Instagram, TikTok and X, in more than 15 languages. With the bravado of sports commentators, many offered hot takes on her game-day attire, scrutinizing, praising and analyzing it.

The most expensive piece in her look was her Ruby Stretch Bracelet from Shay Jewelry, worth US$19,950. In a nod to the Kansas City Chiefs, Swift also added a pop of red with an Erin Andrews varsity jacket, which cost US$129.99.

While most consider style icons to be envelope-pushers, some feel Swift represents a new kind of fashion figure, one who resists the urge to experiment and consistently recycles the familiar – and that’s what appeals to so many people.

“Swift’s commitment to not overthinking things and not making things too highbrow can be defined as genius in its own way – onstage and off,” says Spencer Kornhaber, The Atlantic’s pop-music critic and author of On Divas: Persona, Pleasure, Power.

Swift prioritizes her music above being known as a visual artist, Kornhaber says, alluding to the 14 Grammys she’s won for tracks and albums in which she’s credited as the main or sole songwriter. “With her clothes, she’s taken the sexist, male gaze idea of girl next door and related it to how women see each other platonically – it’s her magic trick.”

Fashion critic Cathy Horyn recently wrote an essay for The Cut, which advocated for Swift – and her long-time stylist Joseph Cassell – to take more risks. Horyn called out Swift’s style for being “basic,” “safe,” “boring” and “disingenuous,” echoing popular memes and TikToks that inscribe photos of Swift, on the red carpet and off, with the words “addicted to never slaying” and “allergic to a cute outfit.” A Reddit group called whatthrefrockk listed 12 outfits in a post titled “A series of Taylor non-serves,” which were deemed “dated” or “stuck in the 2010s” from Etro, Roberto Cavalli and Oscar de la Renta, among other brands.

For Sarah Chapelle, a B.C.-based blogger and author, the amount of criticism Swift has received is proof that the singer is a true force of fashion regardless of what she wears. “Taylor is a style icon because she refuses to be a style icon,” Chapelle says. Much of Chapelle’s forthcoming book, Taylor Swift Style: Fashion Through the Eras, is devoted to this perspective. With sections titled Modern Grandma Chic, The Power of Pastels and Bringing CottageCore to the Masses, the book, out in October, links Swift’s clothing choices to lyrics, personal triumphs, professional hurdles and her lifelong fixation with cats.

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Taylor Swift arrives for the 66th Annual Grammy Awards at the Crypto.com Arena in Los Angeles on February 4, 2024.ROBYN BECK/Getty Images

It also chronicles Swift’s repeat accessories (Dolce & Gabbana handbags), her high-low proclivities and many vintage moments. After dedicating more than a decade to researching more than 7,000 of Swift’s outfits via her blog, taylorswiftstyle.com, Chapelle has deduced that Swift’s strategy in dressing is directly linked to her vast reach.

“She’s trend agnostic so that makes her so relatable to so many generations,” Chapelle says. “Taylor stays away from being too loyal to the same brand for a long time. She isn’t the face of an international fashion house, and she refuses to play the celebrity game in the way it’s been done before. I think that mystifies people.”

One of Horyn’s main issues with Swift was that she stuck to a lot of private schoolgirl attire, and it felt insincere. Chapelle, instead, feels that the repetitive “Academic Horse Girl” themes (think Vassar College crests on tweed vests and twin sets) in Swift’s streetwear reflect what the pop star could have been in another life. For example, much of her early style has swung between broad strokes of nostalgic, girlish Americana style and sticking to variations on archetypes, such as prom queen, princess, and prep-school scholar. So much of Swift’s preppy Gossip Girl-inspired looks, for example, played out in her street-style looks during album releases such as 2010′s Speak Now and 2014′s 1989. London’s Victoria and Albert Museum is currently displaying a number of what curators deem to be Swift’s most iconic looks in an exhibit called Songbook Trail, which focuses on Swift’s costume archive.

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Taylor Swift is seen on October 26, 2023 in New York City.Gotham/Getty Images

“Taylor has said in a few interviews that she missed her prom, so you can see how that plays out on her life and red-carpet moments,” Chapelle says. “During her debut and Fearless eras, she was all about sheeny, shiny fabrics and bustles – it was all very Say Yes to the Dress.”

Regarding the assertions that Swift’s looks are somehow dishonest, Chapelle disagrees. “If anything, having not been a part of traditional teen experiences is probably why she wants to cling to certain aesthetics because it’s her way of being able to live out those opportunities that she may not have gotten to experience.”

Chapelle also says the mix of expensive labels with mall and small online brands, such as Urban Outfitters, Anthropologie and Mazin, a lesser-known jewelry brand, keeps her closer to her fans. “This mix underlines a certain approachable ideal.”

Kornhaber says that unlike Chappell Roan (who has a Courtney Love-goes-to-Las Vegas vision) or Troye Sivan (whose gender-fluid style landed him in Prada and Uniqlo campaigns), Swift does not seem interested in inventing a refined, new world every time she releases an album. He suggests that Swift’s visual messages are often too obvious and her videos “extremely literal” beside artists such as Sivan and Roan.

Swift’s fascinations, whether visual, historical, cultural or literary, tend to draw on East Coast and old-world influences, Kornhaber says, referring to songs such as The Last Great American Dynasty, and various video inspirations pulled from the Gilded Age – an era of American new money after industrialization.

Whatever the case, Toronto-based celebrity stylist Zeina Esmail is reaping the rewards of Swift’s attainable and luxurious style. Esmail is co-owner of the 1132 Consignment, a boutique that curates vintage pieces from brands such as Gucci, Hermes and Chanel (all of which Swift wears). Her most recent big sale came from a Swift fan who purchased a faux fur coat by Des Phemmes – a garment that looks similar to the fuzzy purple Oscar de le Renta coat Swift wears onstage and in the video to her song Lavender Haze.

“We’ve had mothers and daughters who were going to travel to Taylor’s Eras tour stops in Europe already buy a few key pieces that reflect her evolution into upscale fashion brands like Gucci and Etro,” Esmail says.

With reports from the Federal Reserve and Bloomberg Economics indicating that the Eras Tour injected US$4.3-billion to the GDP of the U.S., Swift’s arrival into Canada in November is expected to produce a surge of audience members looking to buy pieces that emulate Swift’s style through the years.

Businesses such as 1132 may draw Swifties, including those from out of town, looking to shop for Eras-inspired concert outfits.

Esmail herself styled Swift for the November, 2014, cover of FASHION magazine during the launch of the album 1989, when the pop star began making more of a concerted effort to wear higher-priced fashion made by houses.

“You can see the confidence she has with what she has started to wear more aggressively [post-1989] and how it has led up to her wearing Schiaparelli,” she says, referring to the custom all-white gown Swift wore with black opera gloves at the 2024 Grammys. “The customers who are fans with tickets that plan on going to her tour stops in Canada are already coming to us for pieces that represent Taylor’s more sophisticated side.”

Esmail says Swift’s point of view can also be seen as educational for fans who are learning about craftsmanship and design, adding that the singer offers a “starting point into luxury that isn’t scary or offensive.” “I like that she’s exploring sexier or more elegant sides of herself these past couple of years because that transformation is teachable without it sounding like a lesson. In many ways, that’s what a good performer can do: simply live, make mistakes and lead by example.”

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