The 29 Best Loafers to Wear With Everything, All the Time (2024)

The OG of loafer manufacturers is still going strong. These are timeless and infallible, with a traditional look that, quite frankly, never goes out of style.

Horse-bit loafers are now a dime a dozen, but it all started with this guy right here. Gucci's quality craftsmanship, burnished look, and chic elegance make this pair stand out from the crowd.

Tasseled-up and hassle-free: a win-win. Cole Haan does comfort and affordability with everyday ease.

From James Dean to Pharrell Williams, the timeless black penny loafer has graced the feet of the best of the best. To Boot's option is sturdy and versatile, whether you want to dress it up for the office or down for the weekend.

If you want to look classy without conforming, opt for a fun, bold loafer. Taft has a wide variety of designs, like this dragonfly jacquard weave that puts a little extra something in your step.

Camper keeps it classy, cool, and comfy. With a lightweight sole and cushioned footbed, this is a loafer you don't have to be afraid of walking around all day in. Plus, with its contemporary look, you can pair it with just about anything, from jeans to dress pants.

These are a bit simple, a bit rugged, a bit classic. With contrast stitching and a sleek, simple silhouette, the minimalist chicness PRL is known for hits the bullseye with these.

Dr Martens are perhaps one of the most versatile loafers out there; wear with jeans, work trousers, anything. They'll last you forever, too.

With sewn-through stitching and a simple saddle strap, these elegant loafers are the epitome of understated luxury.

Ever wonder who started white socks with loafers? It was J.M. Weston, with this iconic shoe. Safe to say: a white sock will look best with these.

Talk a walk on the wild side. (Yeah, I said it.)

Take it from me (or, rather, my father, who has been wearing high-end loafers for decades; hi, dad!)—in the world of luxury designers, Ferragamo is the most comfortable shoe you’ll come across. It’s pretty chic, too.

A style so beloved by one Esquire staffer, that he wrote a whole damn review on it.

For affordable—yet classy—loafers, Dockers has you covered. These are under 50 bucks, but they look like they cost five times that much.

A solid, classic, infallible penny loafer that looks smart as hell with some white socks.

Clarks are known for their comfort, and these loafers are no different. It'll feel like you're wearing your favorite sneaker, but you'll look like a million bucks.

Why not make a statement? Bottega's chunky, lug-sole loafers are classy and cool, whether you pair 'em with jeans or dress pants.

Crafted from fine leather with Brunello Cucinelli's expert hand, these rich brown loafers are elegant AF.

For a classic, black loafer that dresses up any look, Magnanni has a comfortable and chic option that makes even jeans look suave.