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Because I had received so many pats on the back for the Hat, I decided to try for even more the next year (1981) by making proper sailing shorts. Knowing nothing about making clothing, I called on the services of a designer. When that didn't work out, I tried another, then another. Three different designers over a 9-month period!
 Ask and ye shall be told where to go - and whom to see
With a simple phone call I received material help from the Pentagon's clothing consultants (I figured, correctly, that they would know what would last, be comfortable, and be easy to wash and fast to dry, and seldom need ironing). The gentlemen at Genco, a chandlery in Toronto, suggested the marvelous marine-quality, stainless steel, welded-shut D-rings, which we still use (and before that, Hat material and grommets); finding Murray Barrett's (my late dear friend's) wallet lying on the foredeck gave me the idea of incorporating a Velcro-closed security pocket in case the wearer found himself unexpectedly turned upside down; Toronto sailor John Reekie gave me the idea of a flank pocket (he kept important extra stuff in one that he'd sewn in his own shorts).
The "Double-Bum" Shorts
Common Sense said that for strength use the strongest of thread (polyester, but wrapped in cotton so it wouldn't cut through the material), and to sew in lots of stitches (lockstitches, not easily unraveled chain stitches), then bar-tack the heck out of any place that would be stressed - and to double-layer the material in the seat so that friction would be between the two layers, and not between the cloth and a deck, which would wear out the seat quickly.
The time came to drop my shorts
I found a small company to cut and sew them, and because they were (and are) so expensive to make, tried to sell Tilley shorts for $45, But because other shorts at that time were only $30 or so, and because people didn't understand what went into them, sales languished.
By the summer of 1983, two things were apparent: 1: to my surprise and delight, I'd come to realize that the Hat and Shorts were actually the best of their type in the world; 2: I'd had enough; people just didn't seem to want the Shorts so it was time to drop them. I would just stick to the Hats, still selling them mostly from a neighbour's home, and at boat shows. (My "real" work? I had my own business, renting and selling quality works of art to businesses in Toronto. It was boring but doing well, and left me time to mess about with my sailboat, and sell Hats at about 16 boat shows a year.)
The Last Hurrah
But first, since Canada was represented in the 1983 America's Cup races, I presented the team with Tilley Hats, and a special edition of white (not the usual khaki) Tilley Classic Shorts. Then I stopped making them, concentrating on improving the Hat.
But by the fall of 1983, the word about the Shorts had gotten around and at the Annapolis Sailboat Show, people asked for them, and for pants of a similar quality and practicality - not for sailing BUT FOR TRAVEL!
It occurred to me that if I made trousers with a security pocket for a wallet, they would be excellent travel pants. So why not add a secret pocket for a passport?
"By George, Waldo! I've got the makings of a small business. I'll make travel clothing! I'll make it the best in the world! And then I'll make it even better!"
In January, 1984, I set up a small mail-order company. Alex Tilley and Family's Nautical Gear became Tilley Endurables, Inc. and we prospered nearly immediately. (And no, it has not always been easy).
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