Loafers for Work & Play

J.Crew, $198

J.Crew, $198

J.Crew, $198

Summer footwear is all about comfort, versatility and ease. You want a shoe that is so easy, you can pair them with everything in your wardrobe—from your best business attire and your most loved pair of jeans (with a rolled cuff, of course) to your cut-off shorts and swimsuit. And a good pair of loafers can do all of that and always look sharp. But there are two things to keep in mind. First, you want a slightly tapered toe box. Secondly, you want rubber soles. The softer bottomed shoes will ensure that every step is comfy and you never look too formal. This is summer after all.

The Penny

While "penny loafer" stuck as a nickname, it could've easily been dubbed "dime loafer" as people in the '40s and '50s stuck dimes in their Weejuns (enough to make a pay phone call at the time).

Tod's, $625 / $375

Rancourt & Co., $240

Sebago, $165

Cole Haan, $140 / $99.95

Aquatalia, $395 / $197.49

Aquatalia,
$395 / $197.49