$45 / $17, at Urban Outfitters
I've been eyeing these cool Vans Authentics at J.Crew because of their subdued washed colors, and the way the boot laces really class up the canvas uppers. Then I came across these similar sneakers, in a unique eggplant colorway. Despite the bold color, they'd look good with anything from navy, khaki and even a jungle camo patterned pant. It's the type of shoe you can scoop up now to break in, and still wear all summer long with a pair of shorts and a short-sleeved woven shirt. And these here are a lot cheaper than that pre-washed pair. The best part? After a season of wear, the color will be a little worn-in (in the good sort of way), and the shoe will be ten times more comfortable.