It’s got a standard fit and a curved hem, and button-flap chest pockets add a cool blue-collar touch. Brixton Bowery Flannel Shirt, $65, available at Tillys 8.

For instance, navy with a medium blue or forest green and burgundy plaid. Sharper contrasts, such as the classic red and black buffalo plaid, skew more laid back and less refined. (Here are some ...