The flannel shirt is one that's had many lives, from workwear to grunge to urban hipsters and back again. A sartorial contradiction, they're burly and hard-wearing, and yet soothingly soft and warm at the same time. A plaid flannel is the kind of shirt you want to wear when the leaves are falling and the air is crisp. They're the shirts you're supposed to wear with the jackets of the season—tweed, leather, moleskin. And don't be afraid to dress them up either. Just make sure that the check pattern is compact in scale and the fit is trim. And of course, when wearing a more substantial shirt like a flannel plaid, a more textured tie is in order, like nubby wools or square-ended knits.