Kirk Pickersgill, co-founder of Canadian fashion label Greta Constantine, recently returned from Milan where he supported longtime friends Dean and Dan Caten of luxury brand Dsquared2. This reunion highlighted a remarkable 43-year friendship that began during Pickersgill’s 15-year residency in Milan, where he initially worked in the PR and styling department of the renowned fashion house.
Despite current excitement surrounding his label’s 20th anniversary, Pickersgill revealed to Style Observer that fashion wasn’t his original ambition. “My dream was initially to become a cobbler!” he confessed. “I’ve always been fascinated by structure—the composition of heels, soles, and handmade craftsmanship. High school offered little creative outlet, though I wasn’t academically struggling.”
His career trajectory changed dramatically during his final year at North Albion Collegiate Institute when he discovered home economics and sewing classes. This led to a cooperative learning program at fashion house Comrags, where he secured full-time employment after his internship and spent five years refining his design skills.
In 2006, Pickersgill and business partner Stephen Wong launched Greta Constantine, returning to Canada the following year. The timing proved perfect, as Holt Renfrew—Canada’s premier luxury retailer—purchased their entire collection. The brand’s breakthrough came when Harrods’ iconic UK department store also picked up the line, thanks to the support of Camilla al-Fayed (daughter of Harrods owner Mohammed al-Fayed) and personal shopper Raymond Ponce.
The designers found their winning formula combining confidence-boosting bright colors with sculptural ruffles. As documented in The Kit’s 2023 feature, they quickly dressed gala attendees, actors, and wedding parties while staging runway shows in Toronto and New York. Their collections gained international traction across North America and the Middle East, achieving the rare distinction of building a Canadian fashion brand with enduring appeal.
Greta Constantine’s celebrity clientele includes remarkable achievements: Amanda Gorman wore the Keele dress for TIME’s Black Renaissance cover (February 2021); EGOT winner Viola Davis appeared in the Yvresse dress for Ebony’s May 2022 cover; Emmy Award-winning actress Sheryl Lee Ralph selected Resort 2022 for the HCA TV Awards red carpet; Angela Bassett chose the label for the 2021 Emmys; Julia Roberts wore the brand to the Ticket To Paradise premiere (2022); and Meghan, Duchess of Sussex, sported the ‘Kace’ midi skirt during her 2018 Belfast visit.