The 15 Best Loafers to Wear with Everything, All the Time

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Not to 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. Cocktail 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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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. Go ahead and see for yourself how well they pair with anything from jeans to suit pants.

Why we love this brand: It's one thing to be the company that invented penny loafers—it's another to still make chic, stylish pairs that merge contemporary with classic. G.H. Bass has been around for over 150 years, churning out comfortable, stylish shoes (alongside other goodies) the whole time. As far as heritage brands go, it's clear that this one has done its homework: the loafers are as comfortable as they are cool, and it helps that they aren't too pricey, either.

Jordaan Leather Loafers

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—and from the other shoes in your closet.

Why we love this brand: Aside from its impeccably luxurious Italian craftsmanship, Gucci's design is hard to beat. Few brands know how to balance heritage, style, and contemporary looks this well—just see the almond toe, horsebit, and burnished combo in this shoe. You get what you pay for with Gucci, and in this case, it's pure, unadulterated elegance.

The Monterrey Loafers

Tecovas, purveyor of some of the best Western-inspired styles, also has a suede loafer that takes after one of our favorite cowboy boots on the market. These are the go-to pair for when you want to mix it up a little bit from a classic loafer, but you don't want to sacrifice any elegance along the way.

Why we love this brand: You know a cowboy boot brand is good when actual Texans love it. But we don't just love Tecovas for its boots—clearly, the Austin-based label is rockin' with some pretty sweet loafers (and other kicks!) too. What sets Tecovas apart is its commitment to authenticity, cemented in a world where fashion is ever-evolving. That results in styles like this, drawing from cowboy heritage, but spun so as to look perfectly nice with some jeans or trousers in an urban city.

Pinch Tassel Loafers

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

Why we love this brand: Cole Haan is prove that you can get a shoe that feels luxurious on your feet without weighing too heavily on your wallet. Few brands these days can offer quality this good at prices that are also this good, and with its mix of classic and contemporary styles, Cole Haan sticks out from the crowd.

Berle Leather Penny Loafers

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.

Why we love this brand: To Boot doesn't skimp on the details. Its founder, Adam Derrick, is a footwear specialist who knows that quality looks as good as it feels, which is why the brand sources only premium French and Italian calf.

Edric Leather Penny Loafers

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.

Why we love this brand: If you're a frequent Esquire reader, you probably already know that we love Polo Ralph Lauren. What isn't to love, though? The brand does American prep like few others, with a trendy, timeless flair that's always universally flattering.

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, and look great the entire way through.

Why we love this brand: Docs are famously tough, but unlike other sturdy boots, they aren't—how should I put this—ugly. Instead, they're sleek and simple, with polished, flexible leather that molds to your feet over time, creating the perfect fit, just for you.

180 Penny Loafers

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.

Why we love this brand: Like I said—this is iconic! The geniuses behind black loafer, white sock are still crafting finely-made, high-end shoes to this day. Sure, the price is steep, but you get what you pay for: quality and history.

The Ellis Penny Loafers

Talk a walk on the wild side. (Yeah, I said it.) Blackstock & Weber is a beloved choice for loafers of all types, but the brand has some exceptionally cool ones that add a little something extra to your wardrobe.

Why we love this brand: B&W is a brand that's all about reflecting modern life. Its shoes are influenced by contemporary culture, from art to music to fashion, but they retain a timelessness that makes 'em easy to dress up or down, too.

Penny Loafers

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.

Why we love this brand: Like I said—Ferragamo makes the most comfortable loafers out there. Aside from that, though, the fine Italian craftsmanship lends itself to a sleek, luxurious look every damn time.

Vintage Check Panel Leather Penny Loafers

The iconic Burberry checked print makes a cameo appearance in these sleek black loafers, so everyone will know you have good taste.

Why we love this brand: Burberry is one of those heritage brands that just keeps on getting better with age, like a fine wine. Classic British style is imbued into the very core of the label, but with styles like these loafers, it shows that it isn't afraid to shy away from contemporary looks, too.

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.

Why we love this brand: Not only is Camper one of the most comfortable footwear brands I've ever worn, but its one of the most reliable and consistent in terms of style, too. At great prices, the brand makes shoes that feel as good as they look.

Le Loafer Monogram Leather Penny Loafers

The penny loafer dips its toe (ha, ha) into an edgier aesthetic with these clean black loafers, complete with a rubber sole and black metal logo.

Why we love this brand: Saint Laurent is where timelessly chic Parisian style gets a bit of edge. The brand manages to have it all: high quality craftsmanship, pristine, minimalistic styles, and versatility that will favor your ever-evolving wardrobe.

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.

Why we love this brand: Taft is for people who aren't afraid to put a little pep in their step—literally. The brand has a wide assortment of funky, fun prints that make getting dressed—even if you're wearing a simple suit—a little bit more fun.

Monolith Lug Sole Loafers

Prada's iconic chunky loafer is for the bold and the brave. This sizable beauty will give you the confidence you need to strut down the runway of life.

Why we love this brand: When Prada gets playful, it really gets playful, but it never takes away from the brand's sophistication. Take these loafers, for instance—fun, modern, and fresh, but with polished leather and a Prada logo that still announce its high-ranking position in the world of fashion and footwear.

What To Look For

Unlike a dressier pair of shoes, like Oxfords or derbies, there aren't any hard and fast rules you should follow when it comes to styling loafers. Think of them as your sneakers' dressier, classier older brother—they can still hang out on a casual day, but they're ready to tidy up your outfit and get to the office, too.

If you want to get the most wear out of your loafers, look for something that's A) versatile, and B) comfortable. Obviously. Versatility that allows you to wear the loafers with anything from jeans to dress pants will give you the most bang for your buck. And who wants to walk around all day in uncomfortable shoes? Not us.

How We Picked These Loafers

We wear a lot of different loafers, and have seen and tried even more, so narrowing this list down to only 15 options was exceptionally hard work. In the end, it came down to two things: what we know we love, and what we've found our readers do.

The loafers that made it onto this list are Esquire-vetted and approved, picked for the brands' style, quality, and comfort. Moreover, these are best-selling loafers that Esquire readers know and love.

How to Style Loafers

We're living in an era where you can wear loafers with socks or without, with a suit or with jeans. If you're wearing loafers for a dressier occasion, styling them with a nice dress sock will do the trick—just remember to match your shoes to your belt. If you're dressing them down, a white sock is always a classy look, but you can get more playful with colorful and printed socks, too.

Why You Can Trust Esquire

We’re not about writing how great things are if they aren’t actually great. Every product in Esquire’s round-ups are carefully curated by our fashion and e-commerce teams.

When it comes to loafers, you can rest assured that we’re hand-selecting styles that we’ve personally tested, tried, and loved, along with styles that the rest of our stylish colleagues here at Esquire endorse for their own everyday wear, whether that includes coming to work or going to the bar. We've even Endorsed some of these styles because we love 'em that much.

Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two feet are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.

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