Before stadium tours and headline-making red carpets, Taylor Swift was quietly refining her signature style on the streets of New York—this 2014 lineup captures a pivotal moment when her love of vintage-inspired dresses, polished accessories, and standout shoes began to fully take shape.
Taylor Swift’s Iconic Summer Look: Oscar de la Renta Dress and Prada Pumps
Taylor Swift may not exactly be your run-of-the-mill edgy pop artist, but she certainly holds herself well in the fashion department with her selection of ’40s-, ’50s-, and ’60s-inspired ensembles.
Taylor Swift stuns in an Oscar de la Renta floral dress, paired with green Prada pumps and an Elie Saab crossbody bag (Credit: WENN)
Her daytime looks are always classy, put-together, and charming.
On June 20, 2014, in New York City, Taylor Swift was spotted wearing a chic Oscar de la Renta short-sleeve floral-printed dress paired with elegant Prada suede point-toe pumps. She completed her look with a stylish Elie Saab Spring 2012 crossbody shoulder bag.
Taylor Swift in a vibrant, short-sleeve, floral-printed Oscar de la Renta dress (Credit: WENN)
The country/pop singer wore an Oscar de la Renta summery floral dress from the brand’s S/S 2014 collection.
We admire how Taylor chose to wear this floral number with a pair of green pumps and a green bag, which contrast with her adorable day dress. We share the singer’s love for floral dresses.
Taylor Swift wearing a floral summer dress while on a sunny day in the East Village, Manhattan, in New York City on June 20, 2014 (Credit: WENN)
A few weeks earlier, she wore another beautiful dress from the premier Dominican-American fashion designer, renowned for his elegant women’s evening wear, bridal collections, and ready-to-wear lines.
Óscar Arístides de la Renta y Fiallo, known professionally as Óscar de la Renta, passed away just a few months later, on October 20, 2014.
Taylor Swift’s Vermilion Red A-Line Dress by Oscar de la Renta
On May 19, 2014, Taylor Swift wore yet another head-turning outfit when she arrived at the gym in New York City.
Taylor Swift in a red dress and high-heeled shoes while out shopping and going to the gym in Manhattan, New York City, on May 19, 2014 (Credit: TNYF / WENN)
Taylor sported a vermilion red cotton-blend A-line dress from Oscar de la Renta ($1,890), which featured a fitted waist, a scoop neck, darts to the chest, a pleated skirt, a sleeveless design, and an invisible back zip fastening.
She accessorized with a headband by Deepa Gurnani and a cream leather “Sella” tote from Tod’s and completed the outfit with peep-toe slingback sandals by Prada.
Taylor Swift’s vermilion red cotton-blend A-line dress from Oscar de la Renta
Taylor Swift’s Bold Romper and Gucci Heels Turn NYC Street Into a Runway
Two days earlier, Taylor Swift was spotted heading to her gym in New York City. While only outside for a few minutes, she was quickly surrounded by fans and onlookers.
Taylor Swift turned heads in a bold black-and-white SUNO romper paired with sunshine-yellow Gucci suede pumps that perfectly popped against her monochrome outfit in New York City on May 17, 2014 (Credit: Alberto Reyes / WENN)
The American singer wore a coated print SUNO romper with on-seam pockets and an exposed back zip.
She accessorized with jewelry by Red C Jewels and a streamlined satchel by Bhailiu, completing the outfit with a pair of yellow Gucci suede pumps.
Taylor’s black-and-white playsuit was the perfect blend of playful and polished, effortlessly highlighting her famously long legs. Its breezy silhouette and bold contrast made it ideal for a warm spring day in the city.
Her look turned heads and reminded us just how well Taylor pulls off a romper. Over the years, she’s repeatedly embraced the style—whether stepping out casually or gracing red carpets.
Taylor Swift elevated her city-chic romper with bold accessories: a structured mustard-yellow satchel and matching Gucci suede pumps—easy to replicate with a floral romper, color-pop heels, and a sleek shoulder bag in a complementary hue
Taylor’s Gucci pumps featured a bologna construction, a specialized process resulting in a soft, flexible shoe that conforms to your foot. There’s also a tiny interlocking G detail on the back heel and a metal logo under the shoe’s arch.
Gym Chic Taylor Swift Rocks Alexander Wang and Minna Parikka in Soho
The day after attending the Met Gala in a stunning Oscar de la Renta gown, Taylor Swift hit the gym in Soho, Manhattan.
Taylor Swift wore an effortlessly stylish jersey T-shirt dress by Alexander Wang with luxe leather loafers by Minna Parikka (Credit: TNYF / WENN)
She exited the gym sporting a jersey T-shirt dress by Alexander Wang, a fedora by Rag & Bone, Ray-Ban sunglasses, and a pair of leather loafers by Finnish shoe designer Minna Parikka.
Taylor Swift was spotted embracing a casual chic look outside a Soho gym in Manhattan, New York City, on May 6, 2014 (Credit: TNYF / WENN)
Her loafers nodded to Minna Parikka’s signature “kitschy-cool” aesthetic, with sculpted black-and-ivory bunny ears adding a playful, surreal twist to an otherwise classic silhouette.
Minna Parikka “Hop Couture” loafers elevate classic black-and-cream leather with the designer’s signature playful twist—sculpted bunny ears at the vamp adding a whimsical yet polished finish
Taylor Swift Stuns in Urban Outfitters Dress While Shopping in NYC
Taylor Swift has a knack for fashion. She always looks fabulously elegant, whether attending red carpet events or running errands around town.
Another example was Taylor’s look while shopping in New York City on April 22. The “You Belong with Me” songstress looked all geared up for spring as she stepped out in a floral dress.
Taylor Swift looks effortlessly chic in a floral Urban Outfitters dress and green Mary Jane shoes while shopping in New York City (Credit: Alberto Reyes / TNYF / WENN)
Taylor Swift was like a breath of fresh air while shopping in the Big Apple. She wore a golden poinsettia headband and green Shelly Mary Jane shoes, which matched and emphasized the femininity of her Urban Outfitters dress.
Her makeup, including red lipstick and wavy, short blond hair, completed her refreshingly girly look.
The dress featured a vibrant yellow floral print, adding a feminine touch. Crafted from soft woven rayon, it had a keyhole cutout at the scoop neck, a slit back with a button closure, puffed sleeves, and a hidden side zip for a seamless finish.
Taylor Swift accessorizes her chic floral dress with a classic black handbag and a charming golden poinsettia headband, completing her elegant look in New York City on April 22, 2014 (Credit: Alberto Reyes / TNYF / WENN)
From Retro Day Dresses to Statement Heels, Taylor Swift’s 2014 Style Era Still Inspires
These polished 2014 outfits capture Taylor Swift in one of her most memorable street-style phases, balancing ladylike silhouettes, bold color choices, and standout shoes with the effortless confidence that would become a signature.
For more of her best footwear and fashion moments, explore the related Your Next Shoes features below.
👠 Explore Taylor Swift’s Best Shoe & Fashion Moments:
- 📏 Taylor Swift’s height-and-heels breakdown explores how her shoe choices shape her overall style narrative, from towering boots to sleek red-carpet sandals.
- 🖤 Her 2024 MTV VMAs look pairs a yellow plaid Dior ensemble with black Stuart Weitzman Maverick over-the-knee boots for a punk-leaning twist on her polished aesthetic.
- ✨ Taylor Swift’s Billboard Women in Music appearance spotlights gold Sergio Rossi SR1 sandals styled with a navy Oscar de la Renta jumpsuit in one of her sharpest modern power-dressing moments.
- 🏆 Her CMA Awards outfit features Stuart Weitzman “Sultry” sandals that echo the lines of her dramatic cutout dress.
- ⚔️ Taylor Swift’s 2016 Met Gala look leans fully into futuristic glamour with strappy Louis Vuitton gladiator sandals and a bold, edgy Louis Vuitton ensemble.
- 🎤 Her high-waisted shorts era rounds up early-2010s Taylor style, including concert looks built around Keds, oxfords, and other signature shoes from her preppy phase.