When stars land in Toronto, whether it be for a film festival or a press tour, they know who to call to make sure they’re looking sharp for the red carpet — Toronto’s own Jenna Gandy. The tailor, when she’s not altering dresses to perfection for brides-to-be, is often working behind the scenes as a luxury fit specialist for celebrities.
Earlier this summer, it was Gandy who got Bridgerton’s Nicola Coughlan into her show-stopping press tour looks in Toronto — a Sara Mrad silk organza minidress with a flowing cape and a Dior dress. “Because it’s such a time crunch, I was literally chasing her around with a needle for her sleeves!”
It’s a position Gandy has been in many times, trying to beat the clock. She helped sew Taylor Swift into her Louis Vuitton look just before the TIFF red carpet in 2022.
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But her biggest challenge was when Shania Twain asked her to create a custom look for her tour — in less than a day.
“She’s the kind of person who just gives you an idea and lets you do what you think is best,” Gandy says. In the end, it was a matching red crop top and skirt with a train that she pulled together in time.
“It’s funny — I don’t want the pressure, but then I thrive under it and feel this huge relief and want to do it again. It’s like riding a roller-coaster without having to get on the ride,” she says.
Gandy has also become the go-to tailor for emerging Toronto stars, altering Simu Liu’s suits to fit him like a glove and adjusting Maitreyi Ramakrishnan’s dresses to be red carpet-ready.
It’s a position she never could have envisioned for herself when she first joined the fashion school at the International Academy of Design & Technology in Toronto. “But you learn the basics there, and they didn’t really teach alterations,” she says.
So Gandy looked elsewhere to pick up some sewing skills — dry cleaners, factories, retail stores, suit shops. After years of learning, she was ready: her own practice, the Tailorette, was born.
“It’s a lot about learning bodies — kind of like sculpting, in a way,” she says. “If someone lifts weights and has big quads, how do I accommodate that? If someone has long arms or a short torso, your clothes are going to lay differently, so I always work to create balance.”
For Gandy, the art of tailoring is altering an outfit to fit each individual’s specific build so they feel their best. “Self-love is huge; we’re always trying to chase this new version of ourselves. I like helping people feel good in their skin, right where they are.”
Gandy made her way into the industry with men’s suiting, originally fearful of bridal tailoring: “It always seemed like a scary thing.”
Little did she know that she would eventually become a bridal specialist. “It’s all because I love a good love story,” Gandy says of her affinity for bridal tailoring. “I want brides to shine — sending them down the aisle in their dress, it’s like sending a bird out of the nest.”
As someone who is so detail-oriented that her cousins have nicknamed her “The Deets,” Gandy says she becomes ultra-focused on every little part of a wedding dress — so much so that, “I literally feel like I’m in a relationship with the dress! It’s like it has an entity of its own.”
Although stars often look to Gandy as the expert on fit and fashion, she says she’s always learning. “I don’t have 30 years under my belt yet — those are my leaders, my mentors. I just want to keep the beauty of tailoring alive.”
