When you're a bit more buttoned up than usual there's always the spring/summer staple shoe, the suede buck. Walk-Over is a company that's been making them for years, and you can't go wrong with a classic red buck sole and white nubuck upper. Let 'em get dirty over the season. If you want a little more pop, their Derby 100's and Derby Midi's come in any color suede you can imagine, and the soles come in a grip of colors too. These are so versatile, you can rock them with jeans, khakis, or even wear them with a suit depending on the occasion.
Buy It Now at Walk-Over Shoes, $249-255