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

Not toot our own horn or anything, but when it comes to loafers, Esquire has a pretty decent reputation. The modern iteration that we know and love (not to be confused with the moccasin, which Native Americans originated) was first popularized by our editors back in the ’30s. So when it comes to the best loafers, rest assured that we know what we’re talking about.

The most important thing to consider is the variety. The ubiquitous loafer takes on many forms and names: penny, dinner slipper, driver, and Venetian are just a few. What ties them all together is that they are slip-on, no-fuss shoes intended for easy living and, well, loafing around in style. co*cktail party on the horizon? The classic Gucci horse-bit is right up your alley. Looking to cruise down Big Sur or the Amalfi Coast? The dependable Ferragamos are best for that. Want to channel the vibe of a ’30s Esquire editor? The OG loafer, the G.H. Bass Weejun, is what you need.

Now that we're tumbling into autumn, the tried-and-true loafer is more than ready to alternate wears with your winter boots. More than a few Esquire editors have been rocking loafers all season around the office. If you want to do the same, take a gander at the selection below. Buy two, three—hell, get one for every day of the week. Look for something classy and stylish, something that'll go with your wardrobe, whether that consists more of blazers or biker jackets. The loafer has been riding strong for nearly a century and will never go out style. And we here at Esquire called it from the very beginning.

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Best Overall Loafers

G.H. Bass Logan Flat Strap Weejuns

The 29 Best Loafers to Wear With Everything, All the Time (11)

Best Overall Loafers

G.H. Bass Logan Flat Strap Weejuns

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.

Best Horse-Bit Loafers

Gucci Jordaan Leather Loafer

The 29 Best Loafers to Wear With Everything, All the Time (12)

Best Horse-Bit Loafers

Gucci Jordaan Leather Loafer

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.

Best Western-Inspired Loafers

Tecovas The Monterrey Loafer

The 29 Best Loafers to Wear With Everything, All the Time (13)

Best Western-Inspired Loafers

Tecovas The Monterrey Loafer

Tecovas, purveyor of some of the best Western-inspired styles, also has a nifty loafer that takes after one of our favorite cowboy boots on the market.

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Best Affordable Tassel Loafers

Cole Haan Pinch Tassel Loafer

The 29 Best Loafers to Wear With Everything, All the Time (14)

The 29 Best Loafers to Wear With Everything, All the Time (15)

Best Affordable Tassel Loafers

Cole Haan Pinch Tassel Loafer

Now 49% Off

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

Best Penny Loafers

To Boot New York Berle Leather Penny Loafers

The 29 Best Loafers to Wear With Everything, All the Time (16)

Best Penny Loafers

To Boot New York Berle Leather Penny Loafers

Now 30% Off

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.

Best Unique Loafers

Taft Fitz Loafers

The 29 Best Loafers to Wear With Everything, All the Time (17)

Best Unique Loafers

Taft Fitz Loafers

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.

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best comfortable loafers

Camper Walden Loafers

The 29 Best Loafers to Wear With Everything, All the Time (18)

best comfortable loafers

Camper Walden Loafers

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.

Best Designer Penny Loafers

Polo Ralph Lauren Edric Leather Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (19)

Best Designer Penny Loafers

Polo Ralph Lauren Edric Leather Penny Loafer

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.

Best Everyday Loafers

Dr Martens Adrian Snaffle Smooth Leather Kiltie Loafers

The 29 Best Loafers to Wear With Everything, All the Time (20)

Best Everyday Loafers

Dr Martens Adrian Snaffle Smooth Leather Kiltie Loafers

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

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best subtle loafers

Paraboot Coraux Loafer

The 29 Best Loafers to Wear With Everything, All the Time (21)

best subtle loafers

Paraboot Coraux Loafer

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

Best Iconic Penny Loafers

J.M. Weston 180 Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (22)

Best Iconic Penny Loafers

J.M. Weston 180 Penny Loafer

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.

Best Animal-Print Loafers

Blackstock & Weber The Ellis Penny Loafer

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Best Animal-Print Loafers

Blackstock & Weber The Ellis Penny Loafer

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

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best high-end comfort loafers

Ferragamo Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (24)

best high-end comfort loafers

Ferragamo Penny Loafer

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.

Best Versatile Loafers

Astorflex Patnoflex

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Best Versatile Loafers

Astorflex Patnoflex

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

best affordable everyday loafers

Dockers Colleague Dress Penny Loafer

The 29 Best Loafers to Wear With Everything, All the Time (26)

The 29 Best Loafers to Wear With Everything, All the Time (27)

best affordable everyday loafers

Dockers Colleague Dress Penny Loafer

Now 29% Off

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

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best simple loafers

Banana Republic Amir Penny Loafer

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best simple loafers

Banana Republic Amir Penny Loafer

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

best affordable comfort loafers

Clarks Tilden Free Loafer

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

The 29 Best Loafers to Wear With Everything, All the Time (30)

best affordable comfort loafers

Clarks Tilden Free Loafer

Now 54% Off

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.

best chunky loafers

Bottega Veneta Lug Loafer

The 29 Best Loafers to Wear With Everything, All the Time (31)

best chunky loafers

Bottega Veneta Lug Loafer

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

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best luxury loafers

Brunello Cucinelli Leather Tassel Loafers

The 29 Best Loafers to Wear With Everything, All the Time (32)

best luxury loafers

Brunello Cucinelli Leather Tassel Loafers

Now 40% Off

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

best elevated loafers

Magnanni Rafa II Apron Toe Bit Loafer

The 29 Best Loafers to Wear With Everything, All the Time (33)

best elevated loafers

Magnanni Rafa II Apron Toe Bit Loafer

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

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

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