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In Particular, 2014, Was a Big Year for Swift’s Fashion in the Lead up to Her Album 1989. She Wore Lots of Crop Tops and Miniskirts at the Time, Like This Gray Two-Piece Set from Alice + Olivia.

3. the Kitty ‘Accessory’

She Carried Her Cat on a September Day in New York City While Wearing a Classically Preppy Look. the “Love Story” Singer 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.

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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.

By 2015, Swift Had Adopted Tank Tops and Tailored Shorts.

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But in 2016, Swift’s Street Style Had a Brief Rocker Period. Not Only Had the Musician Chopped Her Long Locks in Favour of a Bleached Bob, but She Also Wore Edgier Clothes for a Brief Time.

Eventually, She Returned to Vibrant Colours and Denim Garments. in August 2016, Swift Walked Around New York City While Wearing a Pink Brandy Melville Tank Top Underneath a Denim, Overall-Style Dress from Tularosa. She Also Sported a Black Marni Bag and Flower-Printed Trainers from Gucci.

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She Also Hinted at Her Glamorous Red-Carpet Style with Her Nighttime Looks. One Evening in September 2016, Swift Was Photographed Wearing a Black v-Neck Aritzia Bodysuit Worn Underneath a White Miniskirt from Related Apparel.

9. Playing with Colour

A Few Days Later, Swift Wore One of the Most Colourful Looks of Her Bleached-Hair Era. Her Striped, Long-Sleeved Bodysuit Was from Ph5, While Her Pleated, Burgundy Miniskirt Was from Urban Outfitters.

10. Carefree and Cool

In the Summer of 2018, Swift’s Street Style Began to Reflect the Transition from Her Reputation Album Cycle to That of Lover. She Was Photographed in July of That Year Wearing a Pinstriped Unravel Project Shirt Hanging off One Shoulder and Distressed Denim Shorts from Gucci.

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Swift Fully Embraced the Colourful Side of Her Style in 2019. 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.

12. Bring on the Bling

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She Wore a Black Cotton Dress with a Black Belt Around the Waist, Us$450 Waylon Slide Sandals from Anine Bing, Us$200 Indio Sunglasses from the Same Brand, and a Brown Version of the Us$895 M Frame Box Bag from Mansur Gavriel.

12 of Taylor Swift’s Chicest Street Style Looks Through the ‘Eras’: from Her Zara Top and Floral Gucci Shoes, to the Rocker-Chick Dress from Louis Vuitton and Preppy ‘It’ Girl Moment with Ralph Lauren

By Marcus Vance

• Oct 8, 2026 • 5 min read

12 of Taylor Swift’s Chicest Street Style Looks Through the ‘Eras’: from Her Zara Top and Floral Gucci Shoes, to the Rocker-Chick Dress from Louis Vuitton and Preppy ‘It’ Girl Moment with Ralph Lauren

Direct Answer • Key Takeaway

Swift, 33, Has Been in the Spotlight Since the Mid 2000S, but Her Street Style Really Started to Stand out in the 2010S.

Marcus Vance

Cybersecurity & Digital Privacy Researcher

Marcus Vance is a cybersecurity auditor and technology writer dedicated to educating the public about online safety, data privacy regulations, enterprise security, and emerging cyber threats.

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