Rancourt & Co., $310
These aren't the penny loafers your dad (and even your grandad) wore back in the day. Today's loafers are leaner and meaner than ever. The silhouette has been slimmed down and designers are modernizing the materials along with stepping up the details by adding such tweaks as buckles and brick soles. The resulting slip-ons are more stylish and more comfortable than ever. Not to mention versatile. While we'll no doubt be spending plenty of time this summer in sneakers or barefoot, no other shoe can so easily transition from a backyard barbecue to the boardroom. It's hard not to love a shoe that works in any sartorial situation and not even require socks.