The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (2024)

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Taylor Swift has been in the spotlight since the mid 2000s, but her street style really started to stand out in the 2010s. 2014 in particular was a big year for Swift's fashion in the lead up to her album "1989." She had fun with accessories that year ... including unconventional ones like her cat Olivia. A longtime fashion staple of Swift's, standout coats also played a part in her "1989" wardrobe. By 2015, Swift had adopted tank tops and tailored shorts. But in 2016, Swift's street style had a brief rocker period. Eventually, she returned to vibrant colors and denim garments. She also hinted at her glamorous red-carpet style with her nighttime looks. A few days later, Swift wore one of the most colorful looks of her bleached-hair era. In the summer of 2018, Swift's street style began to reflect the transition from her "Reputation" album cycle to that of "Lover." Swift fully embraced the colorful side of her style in 2019. In 2023, the "Midnights" musician subtly leveled up a simple summer dress with luxurious jewelry. In June of that year, she mixed a bunch of classic pieces to create a casual but cool look. And she showed the fashionable side of cargo pants in September 2023. The following month, Swift stepped out with her boyfriend Travis Kelce — and their couple style stole the show. She put a feminine twist on an athletic style before releasing "1989 (Taylor's Version)." Swift was bejeweled on her birthday in December 2023 with a celestial dress. Her latest street-style look had "Reputation" vibes. References

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Amanda Krause

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The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (1)

  • Outside of music, Taylor Swift is widely known for her sparkling red-carpet outfits and stage looks.
  • But she also has a strong street style, as seen during her New York City strolls over the years.
  • Swift seems to be a fan of statement coats, patterned tights, and denim ensembles.

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Taylor Swift has been in the spotlight since the mid 2000s, but her street style really started to stand out in the 2010s.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (2)

For a New York City outing in November 2011, for example, Swift tucked a navy, cable-knit sweater by Ralph Lauren into a pleated yellow skirt from ModCloth.

Her academia-esque look was completed with magenta Marc Jacobs kitten heels, red lipstick, and a blue Fendi purse that matched the sparkling 13 drawn on her hand.

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2014 in particular was a big year for Swift's fashion in the lead up to her album "1989."

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (3)

She wore lots of crop tops and miniskirts at the time, like this gray two-piece set from Alice + Olivia.

Still, it was her accessories that made looks like the above stand out. She wore vibrant pink pumps designed by Christian Louboutin and carried a yellow version of Dolce & Gabbana's Linda Tote bag.

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She had fun with accessories that year ... including unconventional ones like her cat Olivia.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (4)

She carried her cat on a September day in New York City while wearing a classically preppy look.

She tucked a white Free People top adorned with lace sleeves into a plaid skirt from RD Style, and completed the look with a maroon pair of sheer knee-highs by Tabbisocks.

Swift also wore black loafer pumps from & Other Stories and carried a green Dolce & Gabbana bag.

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A longtime fashion staple of Swift's, standout coats also played a part in her "1989" wardrobe.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (5)

Less than a month after her fifth studio album was released, Swift was photographed spending time with Karlie Kloss in New York City.

She wore a little black dress underneath a tan, tattersall coat, sheer polka-dot tights, and lace-up heeled Oxfords.

Swift also carried a burgundy purse and sported a thin gold headband adorned with a small bow.

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By 2015, Swift had adopted tank tops and tailored shorts.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (6)

For one outing in May 2015, Swift wore an open-back tank top from Zara with black-and-white printed shorts from River Island.

She also added blue patent-leather heels from Pedro Garcia for a pop of color, Swarovski sunglasses, and a Mary Katrantzou bag.

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But in 2016, Swift's street style had a brief rocker period.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (7)

Not only had the musician chopped her long locks in favor of a bleached bob, but she also wore edgier clothes for a brief time.

In May 2016, she was photographed leaving a gathering at Anna Wintour's home while wearing a plaid Louis Vuitton dress with chunky boots and a leather jacket — both from the fashion house.

For accessories, she chose only a small black purse designed by Mark Cross.

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Eventually, she returned to vibrant colors and denim garments.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (8)

In August 2016, Swift walked around New York City while wearing a pink Brandy Melvilletank top underneath a denim, overall-style dress from Tularosa.

She also sported a black Marni bag and flower-printed sneakers from Gucci.

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She also hinted at her glamorous red-carpet style with her nighttime looks.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (9)

One evening in September 2016, Swift was photographed wearing a black V-neck Aritzia bodysuit worn underneath a white miniskirt from Related Apparel.

But her accessories really made the outfit. Swift wore strappy sandals from Louise et Cie, a tan clutch by Aspinal of London, and a white choker necklace from Adornmonde.

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A few days later, Swift wore one of the most colorful looks of her bleached-hair era.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (10)

Her striped, long-sleeved bodysuit was from PH5, while her pleated, burgundy miniskirt was from Urban Outfitters.

She wore both pieces with Michael Kors sunglasses, a Burberry bag, and platform, velvet sandals from Aquazurra.

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In the summer of 2018, Swift's street style began to reflect the transition from her "Reputation" album cycle to that of "Lover."

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (11)

She was photographed in July of that year wearing a pinstriped Unravel Project shirt hanging off one shoulder and distressed denim shorts from Gucci.

While the casual outfit matched the dark aesthetic of her sixth studio album — as did her black leather Tod's boots and Tommy Hilfiger bag — her vibrant lipstick, wavy hair, and Miu Miu earrings hinted at the era to come.

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Swift fully embraced the colorful side of her style in 2019.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (12)

Days before her song "ME!" was released to the world, Swift stepped out in New York City wearing one of her quirkiest outfits to date.

It consisted of a floral Zimmermann dress, a red Mango blazer, and Rupert Sanderson sandals.

The highlights of Swift's outfit, however, were her pink-tinted hair and her cat-printed purse from Anya Hindmarch.

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In 2023, the "Midnights" musician subtly leveled up a simple summer dress with luxurious jewelry.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (13)

After performingthree sold-out shows at MetLife Stadium in East Rutherford, New Jersey, in late May, Swift was photographed outside Electric Lady Studios in New York City.

She wore a black cotton dress with a black belt around the waist, $450 Waylon slide sandals from Anine Bing,$200 Indio sunglasses from the same brand, and a brown version of the$895 M Frame Box Bag from Mansur Gavriel.

But most impressive was Swift's gold, diamond-encrusted Cartier necklace from the 1980s.

The sparkling jewelry — called the Agrafe Herringbone Twisted Necklace — is no longer produced, but one recently sold on 1stDibs, an online luxury marketplace,for $27,250.

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In June of that year, she mixed a bunch of classic pieces to create a casual but cool look.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (14)

She wore a pinstripe shirt from The Row over a pleated Free People skort, and paired both pieces with a baseball cap, lace-up oxford shoes, and a Patou purse.

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And she showed the fashionable side of cargo pants in September 2023.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (15)

Swift's navy pants were designed by Vince, while her sheer, cashmere tank top was by Gabriela Hearst.

She wore them with ankle boots from The Row, a Ralph Lauren baseball cap, and a purse from Yuzefi.

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The following month, Swift stepped out with her boyfriend Travis Kelce — and their couple style stole the show.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (16)

Her chic black-and-gold ensemble featured an$825 houndstooth coat from Gant over a Versace corset top and high-waisted black trousers.

She also carried the $340 Nirvana bag from Aupenand wore a$70 gold necklace from Mazin Jewels. Her updo hairstyle and red lipstick completed the look.

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She put a feminine twist on an athletic style before releasing "1989 (Taylor's Version)."

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (17)

She was photographed in New York City wearing an$850 rugby shirt from Stella McCartney as a dress.

She wore the shirt, which was emblazoned with a golden horse design, with knee-high Prada boots in an auburn shade and a corduroy hat from Ralph Lauren.

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Swift was bejeweled on her birthday in December 2023 with a celestial dress.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (18)

Designed by Clio Peppiatt, the black garment was sleeveless, covered in black sparkles, and decorated with silver moons and stars.

Swift wore the minidress with a fuzzy Anine Bing jacket draped over her arms, platform heels, and a silver Aquazzura bag in hand.

She was also seen wearing a massive teardrop-shaped ring made from opal and blue topaz stones as she left the party. Though many assumed it was gifted to her by Kelce, it was later revealed to have been a birthday present from Keleigh Teller, Swift's friend and Miles Teller's wife.

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Her latest street-style look had "Reputation" vibes.

The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (19)

For an outing to Lucalli Pizza in New York City with Blake Lively, Swift sported a velvet green dress with long sleeves and a short skirt.

She also wore semi-sheer black tights and over-the-knee boots from the Jean Paul Gaultier x Jimmy Choo collaboration.

The shoes, which retail for $2,450, have fans convinced that "Reputation (Taylor's Version)" will soon be released because they're decorated with images of snakes — a symbol of the album and era.

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The best street-style outfits Taylor Swift has ever worn, from minidresses to overalls (2024)

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