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Iconic Canadian entrepreneur Alex Tilley dies at 87

By Nancy Beal

The Canadian entrepreneur who invented the Tilley Hat and a line of outdoor and travel clothing died October 28 of heart failure at age 87 in Muskoka, Ontario. Alex Tilley founded Tilley Endurables, which manufactured its products in Canada, sold worldwide, and supplied hats to the Canadian Armed Forces during the Gulf War.

Tilley wanted to be known as “A Good Man Who Made A Better Hat.”

Tilley was beloved among many Canadians for his “persnickety” dedication to quality, his high standards in customer service (with a lifetime guarantee on his hat) and, perhaps even more, for his creative and humorous advertisements (ever heard of the elephant who ate the Tilley Hat three times?). His endearing and quirky personality permeated Canadian culture for the 35 years he ran the company from its world headquarters in Toronto, where the hat factory was also located.

Born in Mount Albert, Ontario, raised in Kitchener and Sudbury, Tilley obtained his B.A. in Economics and Psychology at University of British Columbia. He moved to Toronto and worked as an art dealer for 15 years before inventing the Tilley Hat in 1980. Precipitated by his frustration with the lack of availability of a suitable sailing hat, his floating, water- and mildew-resistant, high-quality Canadian-made cotton hat became an instant success. In 2015, he sold his company and retired to his home in Muskoka, travelling and volunteering for various charitable causes including Rotary, Habitat for Humanity, and the South Muskoka Hospital Auxiliary. The company is currently owned by Toronto-based Gibraltar & Company, founded by Joe Mimran of “Joe Fresh” fame.

Tilley was passionate about supporting his country, his community and, in particular, young entrepreneurs. He demonstrated his Canadian pride by refusing to have his products manufactured overseas, at great cost to his bottom line. He volunteered extensively and donated to worthy causes including the Canadian Cancer Society, Street Kids International (now Save The Children), the Sir Edmund Hilary Foundation of Canada, and Rotary International. He often spoke to business students, inspiring them as he told his story of triumphs and challenges. He shared his mistakes and often said he “wanted to help them find their way.”

Obituary: Alexander Joseph Tilley
January 8, 1938 – October 28, 2025

With love and gratitude for a life well lived, we share the passing of Alexander (Alex) Joseph Tilley on October 28, 2025, at the age of 87.

Alex will be forever remembered by his wife, Hilary Clark Cole, his daughters Karen Tilley (Jay) and Alison Tilley (Jared), his stepchildren Graham Cole (Sadie) and Melanie Cole (Michael), and his grandchildren Elia and Jack. He is also survived by his dear brother John Tilley, as well as his many wonderful cousins, nieces, nephews, friends, former staff and colleagues, all of whom enriched his life and will miss him deeply.

Born on January 8, 1938, Alex lived a life defined by curiosity, creativity and adventure. He was best known as the inventor of the iconic Tilley Hat, a symbol of practicality, craftsmanship, and the spirit of exploration that mirrored his own values. What began as a personal project to create the perfect sailing hat grew into a hugely successful Canadian brand recognized around the world — one that reflected Alex’s dedication to quality, innovation, and integrity.

Beyond his entrepreneurial accomplishments, Alex was an avid sailor, a passionate traveller, and a lover of life’s simple, genuine pleasures. He inspired those around him with his wit, warmth, and unwavering optimism. His acts of kindness and generosity touched countless lives — from friends and family to the many people who crossed his path through his work and adventures. He made a difference in the world, one person at a time.

A family celebration of life will be held in the summer of 2026, on the water, where he always wanted to be. 

In lieu of flowers, please honour Alex’s memory by spending time outdoors, sharing stories, performing acts of kindness, and embracing the world with the same curiosity, joy, and innocence that he brought to every day of his life.

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