Linsey Woolsey

Fall 2026

Flannel Outfit Ideas, for Men

Frost on the truck. A flannel, open, over a white tee.

A flannel shirt can be worn three ways. Open over a plain white tee, like a light jacket, on a mild Saturday. Buttoned and tucked into khakis, with a crew-neck sweater over it and the collar out, for supper at someone’s house. Or buttoned to the top, cuffs down, when the frost hasn’t lifted by nine.

Frost on the Truck

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A man in an open green and brown check flannel over a white tee, khakis with mud at the knee and cognac leather Chelsea boots leans on a frosted pickup truck in a farmyard at first light.
AI-generated. We'd rather spend a photographer's fee on firewood. The real pieces may look different.

In each, let the flannel be the only pattern. Keep everything around it plain: white, oatmeal, khaki, brown, navy. Choose a muted check, in green, brown or navy, over a bright red buffalo plaid, unless you’re headed into the woods. Brushed cotton, heavy enough to hang straight. Fit matters more than with a dress shirt: the shoulder seam on the shoulder, the cuff at the wrist bone, the hem long enough to tuck.

On the feet, leather boots, Chelsea or lace-up. Khakis or dark jeans both work, so long as they’re plain.

Skip flannel on flannel, a flannel tied round the waist, and a matching hat. Leave it untucked when it’s open, tucked when it’s buttoned.