Olivia De Gregorio _ Lot 57

Independent

Title: Vae Infantem (Woe Baby)

Reflecting on grief and the suggestion of affection through touch, ‘Vae Infantem’ draws on personal experiences as a young widow, using the threat of fire as a metaphor for self-immolation. Surrounded by sundews and jewel beetles, the piece uses codes to connect to Pre-Raphaelite narratives through the language of flowers, symbolist intention, and technical processes. The model, Olivia Da Costa, also wears a one-million-year-old amber earring which was designed and donated by Brandon Hurtado Sandler as a collaborative offering for the work.

Dimensions: 10" x 10" x 1.5"

Medium: Oil paint on wood panel

Value: $2,500

Date: 2025

Painting in oil, Olivia Di Gregorio constructs imagery that reflects multi-states of change and isolation. Her practice operates at the intersection of classical atelier traditions and contemporary psychological inquiry, informed by the tensions of diaspora as a biracial Canadian of Chinese and Italian heritage. Drawing from her foundational experience as a primary caregiver, Di Gregorio explores the precarious terrain of vulnerability through the suggestion of "wished-for" moments of escapism within fantastical planes. These environments allude to lingering dangers and the hidden realities that shape the subject. Her process employs 3D modeling and digital collage to construct preparatory maquettes after the old masters, which serve as the skeleton for an analogue execution using historical materials. This interdisciplinary approach allows for a subversion of symbols from Pre-Raphaelite and Flemish iconography via floriography, addressing the visceral deconstruction of self as a part of evolvement. A graduate of OCAD University and a former painting assistant to Kent Monkman, Di Gregorio is a multi-year recipient of the Ontario Arts Council grant and a 2025 Figureworks Prize finalist. Herwork has been featured in international publications and platforms including Beautiful Bizarre Magazine, BOOOOOOOM, and Divide Magazine. In addition to her studio practice, she serves as a demonstration artist for Winsor & Newton. Following recent residencies at the Pouch Cove Foundation, her work continues to juxtapose a perceived innocence with moments of catastrophe, causing the bloom derived from a seed of chaos.