Target has an impressive resume of designer collaborations, including Diane von Furstenberg, Kate Spade, and Lilly Pulitzer, and now the retailer is adding luxury outdoor company Woolrich to its list.

Dear Mr. Smith: What is your take on the classic red-plaid lumber jacket? Rugged or thuggish? You may be surprised to know that I have two of these heavy cotton overshirts in my wardrobe. One is the ...