Less Prep School, More City Cool: A Loafer Styling Guide

The loafer was introduced in the early 20th century as a casual house shoe. Less stuffy than its laced counterparts, the loafer was designed to emulate Native American moccasins. Prep school students began wearing the penny loafer in the 50s, slipping a penny into the slot of their shoes as a fashion statement. They’ve been a men’s wardrobe staple ever since, with many style updates along the way.

All-too-often spotted beneath salmon pants and ill fitting navy blazers, the loafer is a preppy classic that deserves attention beyond the halls of fancy boys’ academies. Their easy on-and-off construction and elegant lines make them a practical favorite, and with careful styling, they can be the ultimate cool-guy accessory.

Bulk Up

One way to update your loafer look is to choose a pair with a thicker, graphic sole complete with rugged treads. This chunky shoe shape looks fresh and modern, and, when paired with skinny pants, creates a cool and unexpected silhouette. Top it off with an oversize shirt for a look that plays with traditional proportions.

Taste the Rainbow

The market for loafers is flooded with options in brown, camel and black. Explore colorful options for an unexpected touch in any outfit. If neon isn’t your style, go for a pair in jewel-like blue, forest green or moody burgundy instead for a look that’s funky but still sophisticated. Wear these bold loafers with rich-hued separates, like rust-colored wool trousers.

Update the Classics

A loafer is a traditional shoe that looks good with traditional pieces, but freshening the pieces you wear with your loafer through simple styling tricks or slightly altered shapes makes your look more current. Roll your pant legs up two or three times for a hip highwater look, choose a shirt in a graphic print, or sharpen up with a skinny suit — or a combination of all three.

Slip into something a little more stylish with a great pair of loafers. Style thoughtfully and you’ll look sharp and classy without a hint of prep.

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