If you're still rocking your high school sneakers, it's time to start incorporating some grown-man shoes into your wardrobe. Not just for preppy dudes anymore, the dressy slip-on penny loafers are the suave and smart way of showing off your sophisticated side. Be easy—we're not telling you to dress like Don Draper overnight, but one solid pair of proper footwear will get you noticed by top-notch ladies. So before you invest in a pair of Air Jordans, think about how a good pair of penny loafers will last you for years to come. Step in the right direction and check out our Summer Trend: Penny Loafers.