Winn grew up in the Greater Toronto area, graduated from The University of Toronto with a Hon. B.A. followed by a B. Ed.

Currently Winn is represented by Judy Inc. as a creative prop stylist and is also engaged by Sutherland models in their print and talent division.

Winn’s creative styling may be seen in House & Home, Belle and Today’s Parent. A selected list of clients, includes: Clover Leaf, Winners, Birks, Loblaws, Sears, Bell and Canadian Tire.

Winn has appeared in print magazines such as Oprah, Good Housekeeping and Time Magazine; has been engaged by retailers such as The Bay, Nygard International, and Tilley; and as member of ACTRA, has a number of television commercials to her credit.

Winn has produced gala evenings and fashion shows in unique contemporary venues which have included the Atrium at CBC headquarters to Lula Lounge.
In April 2006 Winn produced and co- coordinated a sold out concert at Roy Thomson Hall in Toronto. Over the last thirteen years Winn has produced events that have collectively raised more than $380,000 for various volunteer projects.