The best hiking hat I have ever used is the same one I have been wearing for more than 20 years

I strongly recommend the Tilley Wanderer Cotton Duck Hat because I have counted on mine for well over 20 years, wearing it in the pouring rain, heavy snow, and under the beating sun. Tilley makes the most functional and durable hats I have ever come across, and these are the hats I trust not only for myself but also for everyone in my family.

I got my first, last, and only Tilley hat shortly after the end of my sophomore year of high school as I geared up for a three-week, 250-mile trek across much of the north of Spain. I would be trekking that distance on the Camino de Santiago pilgrimage route along with a small group of other students (and one eccentric but inspiring teacher), our route commencing in the city of Burgos and ending at the cathedral in the center of Santiago itself.

We would average about 15 miles a day (or 24 kilometers, to use the measurements of the land) given a few short days and a few absolute slogs. During that often trying but always charmed trek, I experienced hiking boots that rubbed my feet so raw they bled constantly and would take weeks to fully heal, a cheap foam sleeping pad that afforded only slightly more comfortable than a piece of cardboard, a cheap plastic poncho that ripped along several seams (and yes, it rained often and heavily), and a hiking pack that I could never seem to quite dial in fully, a serious problem given the miles and hours spent with a solid 35-pound gear load on my not-fully-developed body.

In short, I was not all that well equipped for this, my longest and most intense (at the time) overland experience. Now, 22 years later at the time of this writing, I have a half dozen multi-day hiking packs, each perfect for different applications, I have hiking boots suited for snow and ice (crampons optional), for hot weather, for wet conditions, and then, of course, there are all the trail shoes, I have rain gear of all sorts, and on the list goes – I’ll gladly talk gear to no end, just get me going, but for now, let’s focus on the only item from that long ago trek that’s still not only a part of my kit but is a go-to: my Tilley Cotton Duck Hat.

Tilley Endurables, named for founder Alex Tilley, has been making hats since 1980. And that’s handmaking, to be specific. Every hat the Canadian company sells is stitched by a master craftsman using top quality materials, and I can vouch for that because my own Tilley hat has – living up to the brand’s name – endured dozens of downpours, multiple snow showers, several accidental drops (or paddle knocks) into salt and fresh water, and more hours of unrelenting sunshine than I could calculate. And that’s not to mention the gallons of sweat I’ve pumped into the thing.

So they’re tough and durable, which is the takeaway there. And if that were all they were, that would be good enough. But the myriad brilliant, informed design elements built into these hats is what makes them truly remarkable. Like the wind cord that can be looped behind the base of the skull to keep your hat in place in a moderate breeze, tucked under the chin to keep it snug in bigger gusts, or secured both under the chin and behind the head to keep the hat on the head in gale-force winds. Like the dual side snaps that can fold up the brim to promote maximum airflow and wind resistance and to give that awesome desert soldier look. Like the concealed pocket within the hat that can hold cash, a passport, or a picture. (My own hat always has a picture of my wife and kids hidden away within, by the way.) Or like the fact that the hat floats, something, as noted, that has benefited me on myriad occasions. 

Looking at my Tilley hat today, no one is going to think it’s new, but I’d be surprised if anyone not very much in the know weren’t surprised to learn just how old the hat is and just how many times it has served me, from the waterways near my New York home of today to the mountains of my erstwhile California home to jungles and peaks in South America to miles and miles spent trekking across various European landscapes and beyond. With a quick run through the washing machine, some stretching and re-shaping (a knee and a pair of hands are all you need for that), and a bit of time in the sun to dry, the hat always returns to superb condition despite a bit of age showing but showing in that badge of honor way. 22-plus years on, I can’t see myself needing a new Tilley for many years to come, if ever. All that is why this is also the brand of hat I recommended to my wife and that we bought for our son. If they made a hat small enough for our daughter, we’d get her one, too. But that’s OK, as her brother will outgrow his long before it ever breaks down, so we can hand that one down to her and then get him what will, quite likely, be his own forever Tilley.