Consider This: Florsheim Veblen Plain Ox, $175

If you have one pair of "nice shoes," make them brown. You can wear them with a suit, to interviews, weddings, and even on nights out. There's nothing wrong with a tough pair of wingtips, but lately we like the plaintoe oxfords we've been seeing more and more of. It's a simple shoe that goes with anything, and when you're dropping over $100 on a pair of kicks, there better be multiple ways to wear them.