My thoughts on Alex Tilley, Canadian entrepreneur, inventor of the Tilley Hat, and… friend.

It has been more than seven weeks since Alex Tilley’s passing on Oct. 28, 2025 and I find myself thinking of him multiple times a day, reviewing what I had learned about his life and celebrating those highlights.

It wasn’t that way for the first several weeks. Mostly, it felt as if there was a void in the universe without Alex in it. Something was horribly wrong within that vacuum. Perhaps it was because his presence was larger than life… that he somehow took up a little extra room than most. Or perhaps it was because of who he was in my life—the subject of a biography that took me twelve years to write—that I felt his absence more deeply. Or perhaps I was feeling frustrated that I had missed out on the visit I was to have with him, arranged for two days after his unexpected death. I mourned that last chance to spend time with him.

I settled on another explanation, a simpler one: I was missing a dear friend.

People spoke about how Alex was busily signing Tilley Hats in heaven and the thought of that brought a smile to my face. I also told myself that with his various health issues, Alex’s quality of life certainly wasn’t the best over the past year and we all knew it wouldn’t be getting any better.

Although comforting, those thoughts didn’t fill the emptiness in my heart. I came to believe that celebrating his life was the best way for me to work through my grief.

Alex Tilley was a complicated man who took some time to get to know. He hid his persona beneath a well-practiced banter to help him get through his social awkwardness. He despised small talk but loved to talk about the highs and lows of entrepreneurship, about Tilley hats and clothing and, of course, about travel and sailing. I found his observations about the world and the human condition insightful and sometimes surprising. It was often between the lines of his conversations and his actions where I learnt the most about him. I saw a man full of bravado at one moment and intensely modest (even insecure) the next. He was passionate and quirky and lovable and frustrating and brilliant and difficult… all at the same time. There was an intensity and depth about him, but there was also much joy and laughter.

He looked at life through a refreshingly optimistic lens, choosing to see the best in others, stubbornly pursuing excellence and adamantly giving unconditionally to his customers, friends and family. He lived in the moment and savoured life’s adventures.

I celebrate him for the small things (although he did a lot of big things) because the small things feel very big to me.

The small things first… Alex gave generously to those in need throughout his life, often in small, secret gestures. He prioritized his time to share his experiences with young entrepreneurs and business students to “help them on their way.” He prided himself on being a “heavy rescuer” which not only meant he came to the aid of anyone who needed help, but also that he proactively sought to make people’s lives better. He was creative in an “unlimited” way where he didn’t allow his ideas to be constrained by past practices, naysayers or any proclaimed impossibilities.

The big things next… He invented the best hat of its kind in the world. He insisted upon Canadian manufacturing even though it meant much less profit for him. He earned the respect and endorsement of Sir Edmund Hillary. The Canadian Armed Forces selected his hat to adorn our soldiers’ heads during the Gulf War. He chose to offer a lifetime warranty on his hat. He was known as a genius marketer (who else could boast of the elephant who ate the Tilley hat three times?).

I will always think of him in his own words, what he wanted his epitaph to say: A Good Man Who Made A Better Hat.

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