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File consists of photocopies of reflections written by students in response to a presentation given by Winsom for a group of students in New Jersey.

File contains personal records relating to Winsom's travels and activities. Includes a photocopy from a Belize travel guide, a flyer for Whisky Hill Craft Gallery, records relating to celebration of life services for Madgery and Leonard Gardner, and other event invitations and travel records.

File contains professional documents relating to Winsom's work. Includes professional correspondence, a CV, loan agreements for exhibitions, meeting notes, release forms relating to two editions of the publication Canadian Who's Who, budget documents, and other related documents.

File consists of Winsom's business cards, member cards, badges, and name cards for events and speaking engagements. Includes three business cards, a CARFAC member card and five name cards relating to events and talks, such as the Dagara Shamanic African Diaspora Training (2003-2004) and the Belize International Film Festival (2005).

File consists of textual records relating to Winsom's grant applications and awards, as well as grant and award programs that Winsom sat on the jury for or participated in. Includes records relating to the Toronto Arts Council Foundation 2002 Awards, an invitation to a Gala Dinner for the Minister's Forum on Diversity and Culture (2003), a schedule for the ceremony relating to Winsom's Honorary Doctorate from OCAD University (2015), and related documents. Also includes records relating to Winsom's participation in the jury for the First Visual Arts Students Awards for the North York Board of Education in 1995, the Mid-Career Artist's Grant from the Ontario Arts Council in 1999, and a program for the 17th Annual Harry Jerome Awards in 1999. Winsom was commissioned by The Black Business & Professional Association to create a work for the Harry Jerome Awards, which is discussed on page 3 of the program under the title "The Fabric of Life."

File consists of prints, cards and postcards, and other printed material featuring illustrations or images of artworks by Winsom, including a 1996 calendar of Winsom's artworks. Also includes a poster for Reggae Thursdays at Club Safari featuring designs by Winsom that were used without her permission.

File consists of textual records and ten original sketches by Winsom relating to an illustration project for the 1999 edition of Every Woman's Almanac, published by Women's Press. Winsom provided illustrations for the months February, October and November.

File contains five issues of the Women's Almanac (and one duplicate issue) and related printed material relating to the Women's Press. Winsom provided text and illustrations for multiple editions of the Women's Almac,

File consists of original sketches and printed material relating to Granny and Me (1994), a children's book by Gale Henry, illustrated by Winsom. Also includes original sketches relating to the production of OYA, a short video by Winsom.

File consists of 16 pages of sketches and illustrations by Winsom, as well as one dyed textile work of Winsom's name glued to paper. Includes pattern designs, cards, motifs for fabric, and other sketches. Materials are predominantly undated.