The flannel shirt is a classic piece of menswear that's lived many lives, from workwear to grunge to Americana-loving hipsters and back again. Something of 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 tweed, leather and moleskin jackets of the season. Don't be afraid to dress them up either. Just make sure that when wearing a shirt like this, a more textured tie is in order, like nubby wools and silk knits. Or embrace the current '90s revival happening in menswear and pull one on over a loose T-shirt, roll up your sleeves and leave it open—or tie it around your waist on a sunny afternoon.