Way out of my price range but cleverly designed are these boots by Ralph Lauren. First up is the Doogan Plaid Wool Boot.
Redford Plaid Boot.
Ackley Wool Plaid Boot.
Oh. And then the Obrian Calf Shoe. "Sleek shoe handcrafted in Italy from hand-burnished calfskin with two brass buckles at the vamp inspired by luxuriously rugged equestrian style." I'll take one pair, please.