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, letting a Bordeaux Gucci convertible bag serve as the look’s sole 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.
👗 Explore Celebrity Outfits Featuring Topshop:
- ✨ Olivia Palermo wears Topshop tunic and trousers at London Fashion Week, styled with a black sleeveless coat and Tabitha Simmons heels.
- 👑 Kate Middleton’s pink Topshop embroidered dress stood out during her India royal tour, paired with Pied à Terre wedges for a polished daytime look.
- 🎤 Kylie Jenner rocks a green quilted Topshop skirt, pairing it with a cropped top and Chanel boots for an edgy winter outfit.
- 🎬 Maria Menounos styles distressed Topshop jeans with red pumps at the 2016 Sing movie premiere for a chic, casual vibe.
- ⚓ Kelly Osbourne stuns in a nautical striped Topshop dress while attending the 21st Annual Race to Erase MS Gala.
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:
- ✨ Taylor Swift’s punk-plaid Dior moment at the 2024 VMAs was sharpened with Stuart Weitzman Ultrastuart Maverick thigh-high boots, turning a Cher Horowitz-inspired silhouette into something tougher and more stage-ready.
- 🎤 Her record-breaking 2019 American Music Awards look paired a sparkling Julien Macdonald mini dress with Casadei Techno Blade over-the-knee boots for a sleek, leg-lengthening finish.
- ❄️ Taylor’s polished winter mini-skirt outfit leaned into cozy preppy dressing, grounded by brown suede Christian Louboutin knee-high boots with angular block heels.
- 🎉 At Gigi Hadid’s 21st birthday party, Taylor toughened up a sparkly Haney mini dress with towering Vetements platform ankle boots.
- 📚 Her schoolgirl-inspired LAX outfit turned knee-high socks and Christian Louboutin “Mamanouk 120” lace-up booties into a sharp, fashion-forward airport statement.
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