Taylor Swift-Inspired Wellness Activities in Toronto, ON

Emulate your fave eras with on-point styles from Toronto’s fashion and shopping scene.

Lucky enough to get tickets to Taylor Swift’s Eras Tour?

Or are you just inspired by Swift’s headline-making fashion choices?

If you answered yes to any of these questions, Toronto’s fashion scene has you covered. Swifties have endless choices when it comes to shopping a favourite fashion era from Swift’s 10-studio-album discography. Here’s where to shop each look across town.

Style era: Taylor Swift and Fearless

Want to mirror Swift’s ingenue years? Head over to midtown’s Second Nature Boutique in search of the country-inspired florals and ruffled sundresses that Swift favoured from the launch of her self-titled 2006 debut album to her chart-topping 2008 sophomore effort, Fearless.

Second Nature’s selection—which includes embroidered cutout dresses and cuffs with stones—is nothing short of timeless.

To fully finish your look, travel to downtown Yonge Street and try on a few pairs at Bootmaster, home to coveted western footwear brands, including Lucchese, Boulet, Frye and Liberty.

Style era: Speak Now

Few Swifties can forget what is referred to as one of Taylor’s most iconic pieces: the Reem Acra dress she wore on the cover of her disc of 2010’s Speak Now. Swift and her latest styling team loved the dress so much that they recreated it for the Eras Tour with couturiers Nicole + Felicia.

Aside from wedding dresses, Avenue Road’s Estrelle Bridal stocks gowns that mirror the majesty of Swift’s unforgettable fairytale princess looks. Due to the personal attention you’ll receive in this boutique, consider booking an appointment ahead of time.

Style era: Red

Swift’s 1950s pin–up–inspired clothes, which she wore during her Red album period, are quirky, feminine and oh-so-flattering. Riffs on this look can be found at one of the city’s most fun-to-visit shops, Doll Factory by Damzels.

Racks of crimson high-waisted shorts, sparkly tops, cherry-coloured lace dresses and graphic tees—items that Taylor donned for Red, her circa-2012 fourth album—are what local designers Kelly Freeman and Rory Lindo are experts at reimagining in their Queen Street West boutique.

Style era: 1989

Need cool retro looks that don’t break the bank? Look no further than Exile Vintage, located in the walkable and super-eclectic neighbourhood of Kensington Market.

This quintessential vintage hotspot carries buttons and fan merch from new wave bands such as Duran Duran, Wham! and Culture Club (all of which inspired the sound and vision of Swift’s 1989, which was released in 2014).

Pro tip: Grab a snack beforehand with a taco break at Seven Lives Tacos y Mariscos or pie stop at Wanda’s Pie In The Sky, as you’ll need your energy to search through hundreds of vintage tees and jeans from the era of excess.

Style era: Reputation

When Taylor released Reputation in 2017, she was going through some David Bowie-like ch-ch-ch-changes. Her outfits went from feminine and retro to androgynous or rock-inspired.

The city’s main headquarters for rockers seeking second-hand black leather jackets and punk-influenced jeans and tops has been Black Market Vintage Upstairs, a Queen West thrifting hotspot for over five decades now.

Inventory moves quickly, but odds are you’ll find at least one item with Reputation’s main motif, a hissing snake.

Style era: Lover

When Swift had a girls night out with Blake Lively last year, fans flipped out because she was wearing a super affordable mini from Canadian chain, Aritzia.

The cute dress echoed the sorts of looks she pulled out for her 2019 Lover album. Think: a mood board’s worth of sharply tailored, beautifully belted outfits that mixed metallics with LBDs and separates with blasts of colour.

Aritzia’s flagship in the Toronto Eaton Centre shopping mall (on downtown Yonge Street) stocks all of the above, emulating Swift’s style during one of her most romantic music eras.

Style era: Folklore and Evermore

Taylor’s 2020–2022 period—when she released the pastoral albums Folklore and Evermore—can be credited with popularizing granny-style cottagecore vibes throughout closets around the world.

From bohemian blouses and linen peasant tops, to oversized sweaters and crochet maxi dresses, Swiftian vintage pieces can be found at Set Me Free in Toronto’s east-end Beaches neighbourhood—the perfect place to stroll while listening to songs like “Cardigan” and “Willow.”

Budget-friendly and extra-comfy, this shop stocks all the knits, pleats and taupe straw hats that any Swift-ballad-lover (or craft-enthused grandma) could ever desire.

Style era: Midnights

If you’re looking for the kind of high fashion labels that Swift wore during 2022’s Midnights period, look no further than 1132 Consignment, situated within the city’s charming and upscale Summerhill area.

Co-owned by Zeina Esmail, a celebrity stylist who has actually dressed Swift, this high-end boutique is curated expertly. Expect racks and shelves of Swift’s favourite Midnight labels and pieces, from Roberto Cavalli dresses to Dolce & Gabbana handbags (which Taylor has been known to carry on repeat).

Style era: The Tortured Poet’s Department

From Stevie Nicks-esque shawls to private-school-inspired ensembles, equestrian get-ups and beachy wraps, eclectic chain Anthropologie’s fashion range embodies the essence of Swift’s latest disc, Tortured Poet’s Department.

And if you don’t find the right collegial blazer or flowy midi dress you seek, there are plenty more indie fashion and accessories shops along Queen Street West to discover.