Taylor Swift Turns Heads in Topshop Dungarees and Heeled Boots on NYC Date With Calvin Harris

In late May 2015, in New York City, Taylor Swift delivered a masterclass in off-duty dressing—proof that her street style was just as intentional as her red-carpet looks. Known at the time for leg-baring silhouettes and playful minis, the singer shifted gears with a relaxed daytime outfit that relied on proportion, polish, and carefully chosen footwear rather than flash.

Stepping out for lunch with Calvin Harris, Swift grounded her look with sleek heeled ankle boots that subtly added height and structure, reinforcing a style principle that still holds today: when the outfit is simple, the shoes do the heavy lifting.

Taylor Swift wore her shoulder-length bob down with side-swept bangs

Leaving her Manhattan apartment, Taylor Swift stepped out in black dungarees layered over a white Topshop ribbed crop tee—an intentionally pared-back base that allowed her heeled ankle boots to define the look’s structure and proportions.

Taylor Swift steps out in New York City wearing black dungarees over a white ribbed crop top, paired with sleek Topshop ankle boots and a chic Bordeaux Gucci convertible bag

Keeping the focus intentional, Taylor Swift skipped jewelry entirely, allowing a Bordeaux Gucci convertible bag to serve as the look’s single accent.

With her shoulder-length bob worn loose and softly side-swept, the restrained beauty—finished with a natural pink lip—reinforced the outfit’s clean lines and kept the visual emphasis squarely on the structure and lift provided by her heeled ankle boots.

Taylor Swift styled black dungarees with a Topshop ribbed crop tee

After their lunch date at The Spotted Pig in the West Village, the couple looked inseparable as they walked hand-in-hand back to Taylor’s apartment.

Despite the added boost from her Topshop heeled boots, which likely gave her around four extra inches, Taylor Swift’s 5 feet 9 ¼ inches (175.9 cm) frame still looked petite next to Calvin Harris.

Standing at a towering 6 feet 5 ¼ inches (196.2 cm), the Scottish DJ easily measured up well above his stylish girlfriend during their NYC outing.

Taylor Swift holds hands with Calvin Harris, pairing her black dungarees and Topshop ankle boots with a Gucci bag, while Calvin keeps it casual in a grey t-shirt, dark jeans, and Adidas sneakers

This time, she hid her eyes behind a pair of Westward Leaning sunglasses.

Taylor Swift and Calvin Harris leaving The Spotted Pig restaurant and heading back to Taylor’s Manhattan apartment on May 28, 2015 (Credit: TNYF / C.Smith / Patricia Schlein / WENN)

Her leather boots by Topshop highlighted the pop star’s seemingly endless legs.

Taylor Swift’s Topshop “Magnum” ankle boots feature sleek leather, almond-shaped toes, and wrapped architectural block heels that add both height and polished sophistication to her look

The “Magnum” ankle boots have about 4 inches of wrapped architectural heels, almond-shaped toes, and side-zip closures.

The sleek, high-shaft design and sturdy block heels of Taylor Swift’s Topshop Magnum ankle boots create a leg-lengthening silhouette that complements her slim black dungarees

Stepping Out in Style: Taylor Swift’s Most Iconic Shoe Moments

Taylor Swift has consistently showcased her impeccable fashion sense, often elevating her looks with statement footwear. Here are some of her most memorable appearances featuring standout shoes:

Clueless-Inspired Dior Plaid and Stuart Weitzman Boots at the 2024 VMAs

• Event: 2024 MTV Video Music Awards
• Outfit: Taylor channeled a punk version of Cher Horowitz in a yellow plaid Dior ensemble.
• Footwear: She completed the look with black Stuart Weitzman Ultrastuart Maverick over-the-knee boots.
• Read more: Taylor Swift’s Clueless-inspired Dior plaid outfit and Stuart Weitzman boots at the 2024 VMAs

Glamorous in Casadei Over-the-Knee Boots at the 2019 AMAs

• Event: 2019 American Music Awards
• Outfit: Taylor stunned in a custom beaded green Julien Macdonald gown.
• Footwear: She elevated the ensemble with Casadei over-the-knee heeled sock boots.
• Discover more: Taylor Swift’s record-breaking night at the 2019 AMAs in Casadei boots

Edgy Ensemble with Vetements Platform Boots at Gigi Hadid’s Birthday

• Event: Gigi Hadid’s 21st Birthday Party
• Outfit: Taylor wore a sparkly Haney one-shoulder high-low dress.
• Footwear: She added an edge with Vetements leather platform boots.
• Explore her style: Taylor Swift’s edgy look with Vetements boots at Gigi Hadid’s birthday

Schoolgirl-Inspired Look with Christian Louboutin Booties

• Event: Arrival at Los Angeles International Airport
• Outfit: Taylor sported a “Flitter Flutter” shirt by Miss Patina and tan pleated shorts.
• Footwear: She completed the outfit with black nappa Christian Louboutin “Mamanouk 120” lace-up booties and knee-high socks.
• See her look: Taylor Swift’s schoolgirl-inspired outfit with Louboutin booties

These moments highlight Taylor Swift’s versatility and flair in styling knee-high boots, cementing her status as a fashion icon.

Taylor Swift’s Topshop ankle boots are now sold out, but you can shop the latest Topshop shoe styles currently available at Nordstrom.

Topshop “Magnum” Heeled Boots, $160

Super-sleek and chic, this refined ankle boot is crafted from the softest leather and features an almond toe and wrapped, architectural heel for a richly polished look.

Crafted in smooth black leather, Topshop’s “Magnum” ankle boots feature a sleek almond toe and a sturdy wrapped block heel—delivering clean lines, subtle height, and everyday polish that grounds both casual and dressed-up looks