The basic rule with sneakers is this: If you must wear them (at Asylum we believe a gentleman should be shod in a stout pair of brogues whenever possible), the kicks you rock on the street shouldn't look the same as those you wear at the gym. If your sneakers look like the ones your dad wore at the gym back in the 70s, on the other hand, well, that's all good.

Athletic shoe design peaked early. Forget air-cushioned soles, shock-absorbing heels and custom lacing systems -- old-school sneaks were all about clean lines, simple colors and a flattering shape.

Shoes don't come much more old-school than the Nike Cortez, based on the shoe giant's first product. And with a hefty discount, they're now offered at a suitable retro price. ($55.99 from Nike.com)