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.

We noticed Heath in his red-and-black plaid shirt a few weeks ago, which we chalked up to being a Brokeback Mountain memento. Then, we turned a blind eye towards Vince Vaughn in his plaid shirt ...