Buy It Now at Shoe Mart, $529

If there's one pair of shoes you own that aren't sneakers, they should be a hardy pair of longwing brogues. Part formal, part casual, they're dressy enough to make people think you're important, while not so precious that you'll be worried to scuff them up a little. Yes, good ones are pricey, but unlike your Jordans, you can get these resoled and refurbished for years to come. They're like their own retro.