This Father’s Day, we pay tribute to the enduring bond between fathers and sons—a relationship that has long defined the legacy of style at Harry Rosen. Drawing inspiration from an iconic magazine cover that captured Harry passing the business to his son Larry, we recreated this moment in the very same private street near our Bloor location.

This modern interpretation shifts from the act of tailoring a suit to the symbolic passing of knowledge and vision. In the image, Harry prepares Larry and Ian for the next evolution of the brand—grounded in the timeless values he established, yet looking confidently toward the future. It’s a celebration of mentorship, legacy, and the continued pursuit of excellence across generations.Enabling Self-Expression and Finding Your Fit

Creative Direction: Grace Boivin
Filming and Editing: Matt Watkins

he brand moment launched on Father’s Day, while the assets below were shared throughout the shopping season—echoing the idea of passing on a legacy.

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70 Years of Style

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Harold x You: Enabling Self-Expression and Finding Your Fit