THE RULES

1. Sure, they're stylized and debonair, but that doesn't mean you have to wear them with a suit. Let these uptown players have a taste of downtown action by pairing them with your favorite khakis or jeans. John Lobb ($1,510).

2. Speaking of jeans, roll them up to show a little sock when you're wearing double monk straps. With their signature metal buckles, these shoes can handle plaids, stripes and paisleys better than lace-ups. Paul Stuart ($448).

3. Because there are no laces, there's more leather on display with these shoes, so be diligent in caring for them. Double monk straps lose their appeal when they lose their luster. Polish every two weeks or so. Ralph Lauren ($1,250).

Read More:
The Best Wine-Colored Clothing
Tastemaker: Dunhill's Kim Jones
Artisanal America