Skip to content

Tilley founder launches new iconic hat for Rotary clubs

Speaking in Innisfil, Alex Tilley shares the somewhat checkered story of his career, from pumpkins to elephants

Alex Tilley is a Canadian icon, the epitome of entrepreneurial inventiveness.

He’s the founder of Tilley Endurables, a line of clothing known for its quality, practicality and quirkiness.

Tilley was the guest speaker at the Aug. 15 meeting of the Innisfil Rotary Club, and he arrived dressed in Tilley products, from his shirt and pants, to his skivvies.

He generated a laugh when he told the meeting, “In this life, you get what you pay for… Today I’m speaking for free.”

Tilley’s early career was somewhat checkered. His first entrepreneurial success came in Grade 6, when he noticed people selling pumpkins at a house near his school in Kitchener. He went home, brought back his wagon, purchased the pumpkins, “and then I sold them door to door in a wealthier part of town,” making a profit.

Unfortunately, he was hit by a car at age 12, suffering a head injury that made it difficult for him to remember things.

“It’s a bit of a challenge,” Tilley admitted. “On the other hand, I’m fairly bright in other areas.”

Tilley’s father advised him to get a university degree and then go work for Bell, figuring he would have a job for life.

After graduating, Tilley did get a job at Bell. It lasted 30 days.

He started a company that went broke.

He was then hired on by the Bank of Nova Scotia. “That lasted nine months, and then I got fired.”

Tilley just didn’t fit a standard business model, but he could certainly identify a gap in the marketplace.

After reading about corporations having problems with finding artwork suitable for the walls of their offices, he launched Fine Art Consultants of Canada, working with artists to sell or rent artwork to the corporate world.

The venture was a success, but it still left Tilley plenty of time for his hobbies, including sailing a vintage wooden boat.

That’s when, he said, “I decided to make myself a hat in keeping with the beauty and quality of my sailboat.”

The difficulty?

“I do not know how to make a hat. I do know what I want in a hat,” he said.

He worked with a qualified designer to produce what came to be known as the Tilley hat, making a number of changes and modifications that improved both practicality and durability.

When the wind blew the hat off while sailing, he added a “fisherman’s knot” at the back to secure it.

Tilley was 42 when he launched the clothing line that still bears his name. He initially sold his hats from home “because it was a hobby,” for $15.50 apiece – “two dollars more than my costs.”

It was enough to make a profit.

Demand grew. Tilley started selling the hats at boat shows, along with a new line of Tilley shorts.

“I found eventually that people will pay for quality,” so prices went up even as the clothing line expanded, often driven by requests from customers.

Tilley Endurables sold shirts that combined features from both the Cuban and American armies, pants that had pockets sealed with Velcro – “stopping a hand from getting your wallet” – and durable satchels based on a Second World War dispatch bag once sent to him with a suggestion that it would make a good model for a new Endurable.

Tilley’s Unholey Socks, which have a three-year guarantee, are manufactured in Iowa, the only item made outside Canada.

There’s even a line of Tilley underwear, with a unique “secret pocket” for storing valuables.

In fact, there were 1,500 different Tilley Endurable products and models, sold in 18 countries around the world.

Inside each Tilley hat, a label states, “Hand-crafted with Canadian persnicketiness,” and offers a lifetime guarantee against loss or damage.

“I’m a believer in long guarantees. That’s why I put a lifetime guarantee on it,” Tilley said.

He said he used to receive letters and photos from satisfied customers – letters he would quote verbatim, “with permission,” in newspaper ads to help sell his products by “word of mouth.”

Tilley was invited to speak at the Innisfil meeting by Jamie Hardie, who recently worked with the entrepreneurial icon on several marketing projects.

Hardie’s favourite story was based on a letter from an elephant keeper at the Bowmanville Zoo. The elephant liked the hat so much, it reportedly ate it “three times.” Each time, the keeper would patiently wait for the hat to pass through the elephant’s “system," then wash and reshape the hat, good as new.

“Every product seems to have a story, or has made a story,” said Hardie.

Now 80, Tilley is retired.

Two years ago, he sold Tilley Endurables, but still retains a connection with the company.

He has also launched a new venture. He's working with Tilley to produce a line of hats exclusively for Rotarians, embroidered with 'Rotary' and the Rotarian wheel. Ten dollars from the sale of each hat goes to Rotary International.

If it’s successful, he could expand the venture to provide specially designed Tilley hats for other organizations, but right now he’s still testing the market.

“I’m 19 years old, inside my body, but it’s a financial challenge,” said Tilley, who doesn’t use a cellphone or Twitter.

Rotarians at the meeting brought their own Tilley hats, to be autographed by the founder.

“My mother bought me this hat in the '80s,” said Richard Ratte. “It’s been on every canoe trip to Algonquin Park.”

The hat was originally white, but Ratte said he boiled Tetley tea bags and dipped the hat into the brew to get a beige colour.

The Rotarian Tilley hat may not be a big project for the man who put artwork on corporate walls and launched a clothing empire, but Tilley joked, “now that I’m getting on, I’m not as ambitious.”

He has been a Rotarian since 1993, affiliated with both Toronto and Bracebridge clubs, and he hopes the Tilley Rotary hat will be a significant fundraiser for the club.

For more information, or to order, visit

“This is the best hat that has ever been made,” Tilley said. “My ancestor, 12,500 years ago, he was the first person to put a brim on a hat!”

No one at the meeting challenged the claims.

Miriam King

About the Author: Miriam King

Miriam King is a journalist and photographer with Bradford Today, covering news and events in Bradford West Gwillimbury and Innisfil.
Read more