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25 times Taylor Swift effortlessly nailed street style

The 'Better Than Revenge' singer has tried and tested hundreds of covetable looks

Tania Leslau
Fashion features writer
July 8, 2023
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What a time to be alive for die-hard Swifties. Taylor Swift fans have been treated to the re-release of her 2010 album Speak Now, now known as Speak Now (Taylor's Version), meaning many can barely contain themselves. Following her long-term battle to take back the rights to her own material, the singer has remained the focus of the public’s imagination for quite some time, with fans and fellow stars alike heralding her heroic actions.

 In the spirit of Swiftie sensationalism, we’ve decided to analyze not only Taylor's musical influence but also her grip on fashion. It’s no secret that she is a certified fashion girlie, as her wardrobe has spanned cowgirl western-wear to preppy 2010s concoctions and so much more across the years. 

WATCH: Taylor Swift reveals details of new album

Throughout her reign, the global superstar has pioneered iconic silhouettes such as the skater skirt, the traditional Oxford brogue, and the recurring humble Breton striped long-sleeve. Unlike her glitzy on-stage archive that orbits around sequinned bodysuits and billowing gowns, Taylor’s everyday style is more understated, without ever sacrificing the ability to impress.

 So, without further ado, sit back, relax, and enjoy this deep dive into Taylor Swift’s best street-style moments to date.

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Taylor recently enjoyed a meander through New York in a pleated mini skirt, leather loafers, an oversized boyfriend shirt, and a baseball cap.

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As she arrived for a recording session a few days later, the 33-year-old sported a ditsy print corset featuring sweet ruby blooms set against a cream backdrop, structure tailoring and a scoop neckline. She paired the popular piece with some black shorts featuring a relaxed fit that perfectly contrasted the rigid fit of her top and slingback Reformation brogues.

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Taylor channeled fairycore last spring as she was spotted in a white two-piece featuring a sweetheart silhouette top and a coordinating midi skirt.

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Taylor dazzled in a silk blue celestial mini dress as she attended the Republic Records MTV VMA 2022 after-party at the Fleur Room in Chelsea, New York.

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The beloved singer looked perfect in pinstripes as she waved at crowds outside the Beacon Theatre in New York.

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Taylor opted for a velvet plum-hued suit as she arrived at the AMC Lincoln Square 13 theater for a screening of her short film All Too Well in Manhattan.

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 The 33-year-old went all out on the glitter-front in sparkling multicolored trousers and a masculine blazer during a date at Zuma with ex-boyfriend Joe Alwyn. 

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 Think pink was Taylor's outfit inspo for this Barbiecore look. The star wore metallic hotpants and a blossom pink blazer - Margot Robbie would certainly approve. 

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Taylor was a true American dream in denim as she stepped out in a classic striped shirt, distressed shorts and boots in New York. 

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 The star served tourist chic in a large hot pink hoodie that boasted a graphic print of New York as she was pictured stepping out in the Big Apple.

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Tropical goddess Taylor offered up rainforest razzmatazz in a printed short set boasting a foliage-clad design and a shocking pink colour scheme.   

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The singer was a vision in double denim as she hit the streets in a mid-wash denim crop top and black denim shorts.  

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Jungle fever was on the cards with this Taylor creation, which consisted of a khaki playsuit layered over a white baby tee and boho accessorises.  

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A sartorial Francophile, Taylor blasted onto the music scene armed with Breton stripes. The singer often debuted a French-inspired look, like the one above which featured a scoop-neck top and denim shorts. 

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 Taylor was an IRL princess as she was pictured in New York wearing an embellished lavender mini dress and tan-toned heels.

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The polymath musician ensured her airport style was on point as she left LAX in some burgundy shorts and a black long sleeve.  

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 Taylor enjoyed a night out in LA looking angelic in a white flippy mini skirt, mega nude heels and a cropped tank top. 

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 Another example of Taylor's penchant for stripes, the star coolly graced the New York streets in platform heels, hot pants and a long sleeve top.

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A true throwback moment, Taylor blessed us with her presence as she stepped out in a look Jackie Kennedy would approve of. The star looked divinely chic in a pale blossom pink shift dress and leather handbag, paired with some electric blue point-toe heels. 

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If we can glean anything from this list, it's the fact that Taylor really likes shorts. She once again opted for a blue heel to complement some monochrome shorts, complete with a simple black tank top.

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Taylor looked like she had been plucked from the pages of a novella in a sweetheart ditsy green mini dress which she teamed with some daring hot pink heels. 

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The songwriter tapped into Britpop back in 2015 when she appeared in some black high-waisted shorts, a tank top and a black bowler hat.

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Sporting a sun-kissed glow Malibu Barbie would only dream of, Taylor reveled in a spot of shopping. She waved at spectators, showcasing some striped denim shorts, nude high heels and a white longline T-shirt. 

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Her Love Story era consisted of feminine silhouettes and cascading blonde curls, so it would almost be illegal not to include evidence from this blissful period. In 2009, Taylor was snapped in a white cardigan, an array of bohemian thin scards and a floral mini dress.

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The Midnights singer epitomized pop princess style in 2009 when she emerged in a mermaid-esque blue metallic mini dress featuring a vintage cut, a strapless design and a ruffled skirt.

MORE TAYLOR: Taylor Swift Eras tour: A bejeweled return for the world's biggest pop star

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