Born in Jamaica and raised in Canada, Pickersgill has long been influenced by his upbringing. His approach to design can be traced back to his mother Lois, the family matriarch, who glided through the home with elegance, confidence, and grace. For nearly two decades, Pickersgill worked in styling, fashion direction, and merchandising roles in Milan before returning to Toronto in 2006 to begin Greta Constantine with his then design partner, Stephen Wong.
Starting a new business is always difficult, but doing so during a global financial recession demanded that the team operate differently. In lieu of woven or non-stretch fabrications, the brand decided to specialize in jerseys - so that the garment would contour to the nuances in shape of the wearer and not the other way around. If the collection was to empower the consumer, then it would need to do so not only at the party, but also during the morning commute. The cuts were drafted to accommodate individuals with fuller hip and bust measurements.
The approach resonated within the world of celebrity and soon afterwards, Academy Award winners Ariana DeBose, Rita Moreno, and Viola Davis wore their Greta Constantine pieces with the same pride, confidence, and elegance as Lois Pickersgill herself. Now nearly two decades since the brand's inception, Pickersgill continues to lead Greta Constantine with the very same passion, excitement, and drive that fuelled him all those years ago.