I have a confession: I care about how I look while running. I’m a style disaster in any professional setting but will suffer for fashion on the trail. That’s why I’d rather cramp up from lack of water (like I did last year during the Lithia Loop Trail Marathon) than wear a running vest or belt. I’ve been known to wear chafe-inducing cotton shirts because a teenager once heckled me about a tight, shiny synthetic top.
I’ve also sworn off the nerdy, lightweight, tight-fitting, moisture-wicking run-specific hats and have instead opted for a trucker. Now, I consider hats essential, as I’ve spent too many years as a raft guide under the blazing sun. That, plus I hate getting sunscreen in my eyes. But hats tend to have a few inherent issues: They fight the sun but don’t breathe well, they don’t prevent forehead sweat from dripping into my eyes, and they’re ugly.
Over the past couple years, I’ve gone through a number of trucker hats—including an MSR promotional hat that had “Wanna Spoon?” on the panel—but by far the best one I’ve ever tried is The North Face’s Trail.
This hat, which I’ve used nonstop for the past eight months, has all the style of a trucker with some smart technical details. For starters, a purpose-built wicking sweatband keeps my eyes sweat-free, even when I’m running on stupid-hot 90-degree days. The band is twice as thick as what you’d find in a normal cap and absorbs, then wicks, all the water coming out of my pores.
Unlike normal trucker hats with solid, not-very-breathable front panels, the Trail comes with a perforated panel with holes so big I can stick my pinky through them. Out back is regular mesh. Combined, all those breathability features make for a hat that vents like a cheese grater when I run. There’s constant airflow.
The Trail is also comfortable for long stretches at a time, thanks in large part to its flexy bill. This might seem like a minor detail, but it creates a lot less pressure on my forehead than a rigid bill, so I can stand to wear the hat for the time it takes to run a 50K.
The only two downsides are price and bacteria buildup. The thick headband can get funky: I have to be careful to hang the hat in in the sun after a long run, and maybe (gasp!) hand-wash it occasionally. And at $30, the Trail is at the top end of the trucker hat market and probably costs five times what you’d pay for a gas station option. But compared to other pieces of gear—like, say, your pricey shoes—it’s a reasonable investment. Sometimes you have to pay the price for looking good.
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