I love Timberland Boot Company — I wore a pair today — which is why I’m excited to have a pair of Counterpane Spectator Oxfords (retail $250) to give away this week.

Timberland Boot Company shoes and boots not only cool with a laidback, yet dressy look and feel, but they’re extremely durable and the most comfortable pair of shoes I’ve ever owned. I’d say they’re as comfortable as Rockports, but I’ve never even been within 10 feet of a pair so I’m only guessing.

Click here for your chance to win.