The 5 Best Wool Shirts

Modern wool shirts are comfortable and easy to wear, while also being great at regulating body temperature. Here are our picks.

Sure, wool shirts are the kind of apparel worn by your grandfather when he would go hunting in the backwoods. Big, blocky red and black plaid patterns with buttons the size of radio knobs, right? We already know what you’re going to say. “I won’t wear a wool shirt. They’re itchy and uncomfortable. I don’t care if they keep you warm.”

You wouldn’t be alone in your opinion, but you’d certainly be wrong, especially if you were introduced to modern wool shirting. Wool shirts are making a bit of a comeback, but it’s more of a redefining. It’s not just about outdoor type styles but also for dress and casual office wear. Wool shirts run the range from thin and sophisticated to thick and burly.

The quality and weave of some of the newest wool shirts have changed such that they’re now superb even in summer. In fact, wool’s properties equate to keeping you cool in warm weather and warm in cold weather, even when the fabric is wet. It doesn’t cling to skin and pulls moisture away from the body naturally. What’s more, they don’t wrinkle and also don’t hold odor like synthetic fabric or cotton do, so you clean them less often.

They tend to cost more, but the idea is that they last longer. Better to own one great shirt that you absolutely love than have a closet full of crappy ones that you feel forced to wear because you paid for them.

Thick or thin, casual or semi-formal. Here are our favorite wool shirts for this fall season. You’ll find yourself coming back to them over and over again, and it might be your new favorite shirt fabric.

pendleton wool long sleeve button down shirt

Pendleton Board Shirt ($149)

When we can find a great shirt to complement our rugged and refined boot fetish, we’re thrilled, and the board shirt is a solid candidate for the position. The patterned button up uses virgin wool that is water, odor, and stain-resistant.

Plus, it’s a proven style for Pendleton since it’s based on their iconic field shirt. What’s more, you can machine wash the sucker, so it’s low maintenance. Not that you’ll have to wash it that often since wool naturally sheds odors. Pair it with a great pair of  boots, and you’ll never look like you’re trying too hard but just enough.

merino wool checked pattern long sleeve button down shirt

Wool & Prince Button-Down Shirt ($108)

CEO and founder Mac Bishop knows a thing or two about American-made apparel. With his father and grandfather having worked at Pendleton Woolen Mills, he grew up surrounded by it. In 2013, he founded Wool and Prince after growing ever frustrated with the high maintenance and short life of cotton dress shirts. He created a 100% wool shirt and tested its mettle by wearing it for 100 days unwashed and unironed, proving that wool’s properties are superior to cotton.

Their line of dress shirts and work shirts, designed in Brooklyn and impeccably made in Shanghai, are built to last and fit like they’re custom made. Our favorite is the button-down shirt in merino wool. It’s cut in their signature fabric weight, and the untucked casual style seals the deal for us. It can go with jeans, chinos, cords or wool slacks with equal aplomb. This is one shirt you’ll have for years, and it’ll surely outlast every other shirt you own, except perhaps for the ones you never wear.

man wearing a long sleeve button front wool shirt

Icebreaker Merino Flannel Shirt ($220)

If you haven’t worn anything by Icebreaker, you’re missing out. Their casual and athletic wear sourced from New Zealand merino wool are well-designed and incredibly well made. From hoodies and tights to sweaters and even underwear, their super-soft wool will make you a convert. The Merino Flannel Shirt can work untucked or tucked, for that more professional look, and it makes for the perfect cold weather wardrobe essential with 100% merino wool to help regulate body temperture. You could easily wear this with some flat front khaki shorts as you could with dark denim jeans.

man wearing a wool plaid pattern shirt

Woolrich Alaskan Melton Recycled Italina Wool Shirt ($220)

If you’re looking for a wool shirt that blends ruggedness and refinement, it’s the Alaskan, and Woolrich has seen fit to make this one right here in America, which we love. Woolrich uses a blend of recycled Italian yarn to create a button up that has a modicum of texture for a look that’s not overly casual nor dressy while providing a bit of stretch. The two snap button flap front pockets give it a work shirt aesthetic, along with a classic pointed collar and the clean lines of the Archival checked pattern . It’ll look properly handsome with any one of these great pairs of upgrade jeans.


Libertad Style + Performance Travel Shirt ($129)

Libertad’s version of the wool button up shirt is geared towards the traveler but really communicates a dressier appearance thanks to its rich colors and crisply cut shape. The travel versatility can be attributed to the 100% merino wool fabric made with modern techniques that transitions well between climates.

Forget wearing a cotton shirt when you fly for business meetings. This is the right choice thanks to its anti-wrinkle and moisture wicking properties that will have you looking like you had your own dry cleaner on the plane when you disembark. Pair it with a smart blazer and you’re ready for the skyways and byways.

Amos Kwon

Amos is an aficionado of cars, cigars, watches, whisky, tech, and style. He's written for Gear Patrol, Askmen, Inside Hook, and Fatherly. He's based in the Chicago area and lives with his wife and three children. Follow him on Instagram @wrathofkwon.