Olivia Di Gregorio
Bio:
Olivia Di Gregorio is an internationally exhibited and published new generation artist in Toronto, having graduated from OCAD University in 2019 with a Bachelor of Design in Illustration, and a minor in Drawing & Painting. Since graduating, Di Gregorio was chosen as a finalist in the Traditional Art category for the Beautiful Bizarre Magazine Art Prize in 2021, and has exhibited work in international galleries from San Francisco, Denver, South Korea, and the UK. Her paintings have also been published in Supersonic Art, and BOOOOOOOM’s ‘Tomorrow’s Talent’ Vol. II, Vol. III, and Vol. IV. Last year, Di Gregorio was invited to be a resident artist at The Pouch Cove Foundation in Newfoundland, and was recently selected as a finalist for the 2025 Figureworks Prize in Ottawa.
Artist Statement:
Painting in Oil, Olivia Di Gregorio’s imagery reflects multi-states of change and isolation. Her experiences with diaspora as a biracial Canadian of Chinese and Italian heritage, and as a caretaker for those who’ve been physically ill guide her attempts to express wished-for moments of escapism within ethereal planes. Integrating moments of hardship and elements of lingering dangers, Olivia’s paintings allude to the hidden realities within the environment that will shape the subject. Juxtaposing innocence with the chaotic nature of the deconstruction of self as a part of evolvement, we see Di Gregorio’s work depict moments of catastrophe causing the bloom derived from a seed of chaos.
Portrait by Hal October, 2018
Curriculum Vitae
Education + Training
2020
- Grand Central Atelier, Light and Form Online Workshop, Still Life Online Workshop, New York City, NY. July 31st – Oct 30th
2019
- Bachelor’s of Design in Illustration, and a minor in Drawing & Painting, Ontario College of Art and Design University (OCAD U), Toronto, ON
2018
- Angel Academy of Art, Painting from the Live Model Summer Workshop, Florence, TOS. July 16th - 27th
Solo Exhibition
2021
- Children of a Midnight Spring, Likely General Gallery, Toronto, ON
Select Group Exhibitions + Art Fairs
2025
- (Upcoming) Rare Phenomena, WOW x WOW, Online Exhibition, UK
- MicroVisions 8, WOW x WOW, Online Exhibition, UK
- Figureworks, Wallack Galleries, Ottawa, ON
2024
- Revival, WOW x WOW, Online Exhibition, UK
- Women, James Baird Gallery, Pouch Cove, NL
- Silent Soliloquies, WOW x WOW, Online Exhibition, UK
- MicroVisions 7, WOW x WOW, Online Exhibition, UK
- Youth, Truth, and Imagination, Joseph D. Carrier Art Gallery, Toronto, ON
2023
- Intertwined, WOW x WOW, Online Exhibition, UK
- Main Show Exhibitor, IX Art Show, GoggleWorks Center for the Arts, Reading, PA
- The Eclectic Majestic, WOW x WOW, Online Exhibition, UK
- Memory Hive, WOW x WOW, Online Exhibition, UK
- Phobic Shadows and Moonlit Meadows, Ryan Joseph Gallery, Denver, CO
- Buried Connections, WOW x WOW, Online Exhibition, UK
2022
- Renewal, WOW x WOW, Online Exhibition, UK 2022
- Mystical Rhythms, WOW x WOW, Online Exhibition, UK
- WOW2, WOW x WOW, Online Exhibition, UK
- The Portrait Show X, Modern Eden, San Francisco, CA
- ‘Within The Static’, WOW x WOW, Online Exhibition, UK
2021
- The Portrait Show IX, Modern Eden, San Francisco, CA
- Toronto Outdoor Art Fair, Online Exhibition, Toronto, ON
2020
- Toronto Outdoor Art Fair, Online Exhibition, Toronto, ON
- Artist Untapped: Artist Project 2020, Better Living Center, Toronto, ON
- December Group Show, Galerie D’Este, Montreal, QC
2019
- Daegu Art Fair, Partial Gallery, Daegu Convention Center, Buk-gu, South Korea
- Homeless and Healthy, OCADU U Life Painting Group, University of Toronto, Hart House, Toronto, ON
- Transformation: Witchfest North 2019 Art Exhibition, Beaver Hall Gallery, Toronto, ON
- Why The @#&! Do You Paint? : Meaning, Gladstone Hotel, Toronto, ON
- Ada Slaight Studios Celebration Exhibit, OCAD University, Toronto, ON
- EXUBERANT: Presented by the Women’s Arts Association of Canada and OCAD University, Women’s Arts Association of Canada, Toronto, ON
- Art History Matters Exhibition, University of Toronto, Hart House, Toronto, ON
- Grad Ex 104, OCAD University, Toronto, ON
2018
- OCAD University Illustrative Drawing and Painting Exhibition, Artscape Youngplace, Toronto, ON
2017
- NANOPARTii, The White House Studio Project, Toronto, ON
Auctions
2023
- Art With Heart, Casey House, The Carlu, Toronto, ON
2022
- Canadian Tire Jumpstart Charities Auction, Toronto, ON
Awards and Grants
2025
- Ontario Arts Council, Materials for Visual Artists Grant, ON
- Figureworks Prize Finalist, Ottawa, ON
2023
- Ontario Arts Council, Materials for Visual Artists Grant, ON
2022
- Ontario Arts Council, Exhibition Assistance Grant, ON
- Ontario Arts Council, Project Grants for New Generation Artists, ON
2021
- Beautiful Bizarre Art Prize, Raymar Traditional Art Award Finalist, Australia
- Ontario Arts Council, Exhibition Assistance Grant, ON
2020
- Artist Project Untapped Finalist, Toronto, ON
2019
- Partial Gallery Membership (Alumni), OCAD U Career Launchers, Toronto, ON
2017 –2018
- Creative Quarterly, CQ52, Fine Art Runner-up, Student category, New York City, NY
- Creative Quarterly, CQ50, Fine Art Runner-up, Student category, New York City, NY
Residencies
2025
- The Pouch Cove Foundation, July, St. John’s, NL
2024
- The Pouch Cove Foundation, September, St. John’s, NL
Select Publications and Press
- “Issue 13” Divide Magazine, publication date: February 24th, 2025
- “Tomorrow’s Talent Volume IV Art Book” BOOOOOOOM, publication date: September 30th, 2024
- “Tomorrow’s Talent Volume III Art Book” BOOOOOOOM, publication date: August 1st, 2023
- “Ethereal, beautiful works by Canadian artist Olivia Di Gregorio” Supersonic Art, Zach Tutor, publication date: February 15th, 2022
- “RAYMAR Traditional Art Award 2021: Finalists Announced” Beautiful Bizarre Art Prize, publication date: August 20th, 2021
- “Tomorrow’s Talent Volume II Art Book” BOOOOOOOM, publication date: April 9th, 2021
- “Artist Project 2020: Interviews” Sidewalk Hustle, Kathryn Kyte, publication date: February 24th, 2020
- “What to See at Artist Project 2020” Sidewalk Hustle, Kathryn Kyte, publication date: February 21st, 2020
- “Exhibition Programme 1” Intaglio: University of Toronto Art Journal, publication date: May 31st, 2019
- “Issue 2", Cross Process, Toronto, Canada
Other Experience
2025
- Winsor & Newton Demonstration Artist
2022 - 2025
- Teaching Assistant/Tutorial Leader for ‘Contemporary Painting’ at OCAD University
2019 - 2021
- Painting Assistant at Kent Monkman’s Studio