I’m a hat person out of necessity. Thanks to several years of high-alpine living and more

I’m a hat person out of necessity. Thanks to several years of high-alpine living and more than my fair share of sunburns, I’ve tried embracing trendy wool wide-brim hats and summer sun hats made of straw. However, nothing really fits the, ahem, bill for me like a trucker hat. Now a staple for bad-hair days and a symbol of a life lived outdoors, trucker hats get their name from the fact that they were originally given away as freebies to truck drivers, farmers, and other rural workers in the 1960s as promos from farming-supply companies. But over time, their popularity has grown to the point where nearly every outdoor brand has at least one in its lineup. With so many options on the market, I picked these favorites by focusing on a few key things—company ethics, overall quality and durability, and style. Here are the ones that rose to the top. “My Meridian Line hats are designed from the inside out—every stitch and piping and internal art considered,” says Jeremy Collins, an illustrator whose imagery has saturated nearly every niche of the outdoor industry. He’s worked with everyone from Keen to Protect Our Winters on highly recognizable marketing campaigns. In 2014, he cofounde...

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When you buy something using the retail links in our stories, we may earn a small commission. Outside does not accept money for editorial gear reviews. Read more about our policy. Considering you’re probably going to be wearing one every day for the rest of the season, you can never have too many beanies. We picked six of our favorite styles to keep you warm and stylish through the winter months. An understated beanie can go with nearly any outfit. This one from Upstate Stock is made from acrylic and mohair and sewn here in the United States. It’s light and warm, and you can rock it cuffed or uncuffed, depending on your mood. Coal partnered with Protect Our Winters for a beanie that’s produced using 76 percent less energy, 85 percent less water, and 76 percent less waste than your standard acrylic beanie. The secret ingredient is a Polylana yarn, which is made from new and recycled polyester.  If your style is more colorful, you’re going to love the Herschel beanie. Choose from wild patterns like ducks, raccoons, or narwhals. Whatever design you choose, the build is a simple but effective acrylic with an outgoing pom. The Emilime is hand knit from soft alpaca wool for ultimate ...