Greta Constantine fashion designer Kirk Pickersgill has just returned from a quick trip to Milan, Italy, where he supported long-time friends Dean and Dan Caten, founders of luxury fashion house Dsquared2. The Canadian twins and Pickersgill have a solid 43-year relationship. Indeed Pickersgill, who lived in Milan for 15 years, worked with the label’s PR & Styling department.

Exhausted from his flight, but upbeat about interest in his label’s 20-year milestone, Pickersgill reveals to Style Observer (SO) that fashion was not top of mind. “My dream was [initially] to become a cobbler!

“Back then everything was made by hand. I was interested in the composition of the heel, the sole; I love structure. In high school I was not an academically bad student but there was little or no creative outlet.”

Things changed, however, in his final year at North Albion Collegiate Institute. He attended home economics and sewing classes. On graduation he got into a co-operative learning programme at fashion house Comrags, where he secured full-time employment post-internship and spent five years honing his design skills. Needless to say, his dream of designing shoes was put on pause. The self-taught designer, along with business partner Stephen Wong, started Greta Constantine in 2006, a year before returning to Canada. “It was time,” he states, even as he describes his time in Milan as “the best years of my life”.

Truth be told, there was little time to look back. Holt Renfrew, Canada’s haute retail endroit, had purchased the entire Greta Constantine collection and, too, the iconic UK luxury department store Harrods. Camilla-al-Fayed, (Harrods owner Mohammed-al-Fayed’s daughter) and Raymond Ponce, Harrods personal shopper, were instrumental in securing the collection.

Wong and Pickersgill had found a winning formula and were on a roll. As stated in The Kit in a 2023 article by Rani Sheen: “They dressed gala-goers, actors and wedding parties in confidence-boosting splashes of bright colour and sculptural ruffles. They staged runway shows in Toronto and New York; picked up retailers in Canada, the US, and the Middle East; and through it all unlocked a rare achievement: A Canadian fashion brand with longevity.”

1. Amanda Gorman — the youngest Inaugural poet in US history — covers TIME’s The Black Renaissance issue in the Greta Constantine Keele dress, February 2021 (Photo: Awol Erizku)

Actress Viola Davis, who has earned the rare and coveted #EGOT status — winning an Emmy, Grammy, Oscar, and Tony — was photographed by Keith Major wearing the Greta Constantine Spring 2022 Yvresse dress for the Ebony May 2022 cover. (Photo: Keith Major)

Emmy Award-winning actress Sheryl Lee Ralph arrives on the 2nd Annual HCA TV Awards red carpet rocking Greta Constantine Resort 2022. (Photo: IG/@gretaconstantine)

Actress Angela Bassett attended the 2021 Emmys in Greta Constantine Resort 2022. 

Julia Roberts wore Greta Constantine to the Ticket To Paradise LA premiere, 2022. (Photo: IG/@gretaconstantine)

(Photo: IG/@gretaconstantine)

Meghan, Duchess of Sussex, donned a Mackage Mai coat, Victoria Beckham sweater, Greta Constantine ‘Kace’ midi skirt in teal, “Oxid” Jimmy Choo pumps, and a Charlotte Elizabeth Bloomsbury bag on her visit to Belfast, Ireland — March 2018.