Last year, I inherited an old button-up wool shirt in red and black buffalo ... plaid, I put it in there.” The folder’s contents include sleeves from Caribou Coffee cups, a Farm Bureau ...

Sharper contrasts, such as the classic red and black buffalo plaid, skew more laid back and less refined. (Here are some of our other favorite dress shirt picks.) Feel and fit are important.

1850: Pennsylvania-based Woolrich Woolen Mills creates the first buffalo plaid flannel shirt. Workers instantly love the warm, practical button-up and its red-and-black checked pattern.