When Alex Tilley lost yet another poorly made hat to the winds while sailing his restored 30-foot boat, he decided—as a hobby—to design his own hat. Soon, every sailor in Toronto wanted that rugged and durable hat, and the hobby went full-time. Fast-forward nearly 35 years, and Tilley Endurables hats, clothes and accessories are seen on travellers around the world. Proudly Canadian, Tilley feels duty-bound to make virtually everything in Canada. Tilley loves to see the world, but his favourite place is still at the helm of his old Bluenose sailboat in the waters of Lake Muskoka. 

What’s a “must-have” in your suitcase?

It might sound silly until you need it, but I’ve now added a Tilley Emergency Travel Cord to my bag. It’s a two-metre-long cordura shoelace. It comes in handy as a clothesline or when a suitcase breaks, or to secure a carry-on to a roller bag. 

Days on the road?

Generally, I travel twice a year now. As the ambassador for my company, I’m decked out entirely in Tilleys, of course. 

Top packing tip?

I pack lightly, making sure my clothing is all colour-coordinated. By wearing only Tilleys, including a vest and a shoulder bag, and carrying a very lightweight, packable backpack, I only need cabin luggage. 

Favourite Canadian destination?

I like rocks, trees and lakes, so that keeps me happy in the Muskoka. But I envy Albertans for their mountains.

Dream destination?

i’ve been to over 50 countries, but have yet to visit Iceland. I’m very interested in volcanoes and glaciers.

Latest adventure?

For fun last Canada Day, we travelled to Tilley, Alta., [about 2.5 hours southeast of Calgary] to participate in the celebrations, and we gave away lots of hats. 

Best business advice?

I didn’t invent a hat, I just made my hat better. Whatever you do in business, you must do better than anyone else. You must stand out in the crowd, be memorable. Also, most new businesses fail because of the owner’s inexperience. To succeed, find a business mentor. His or her experience can save you.