The 13 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 of the loafer 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 many forms with many names: Penny, dinner slipper, driver, and Venetian are just a few. What ties them all together is that they’re 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 Pradas 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.

When we’re tumbling into autumn, the tried-and-true loafer is more than ready to alternate with your winter boots. More than a few Esquire editors have been rocking loafers around the office all season. 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 of 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 be making chic, fashionable pairs that merge contemporary with classic. G.H. Bass has been around for over 150 years, churning out comfortable, stylish shoes (and other goodies) the whole time. Among heritage brands, it’s clear that this one has done its homework: Its 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. The quality craftsmanship, burnished look, and chic elegance of Gucci’s loafers make them 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 look this well—just check out that almond toe, horse bit, and burnished leather combo. You get what you pay for with Gucci, and in this case, it’s pure, unadulterated elegance.

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 when you want to mix it up by straying a bit from the classic loafer but you don’t want to sacrifice elegance.

Why we love this brand: You know a cowboy boot brand is good when actual Texans love it. But we don’t love Tecovas just 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 in the ever-evolving world of fashion. That results in styles like this, drawing from cowboy heritage but in a way that looks perfectly nice with jeans or trousers in an urban setting.

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 proof 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 a price that is 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 leather.

Edric Leather Penny Loafers

These are a bit simple, a bit rugged, a bit classic. With their contrast stitching and sleek, understated silhouette, the brand known for minimalist chicness hits the bull’s-eye 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 but timeless flair that’s always universally flattering.

Adrian Snaffle Smooth Leather Kiltie Loafers

Dr Martens offers one of the most versatile loafers on the market—wear them with jeans, work trousers, anything. They’ll last you forever, too, and look great the entire way.

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: As I said, these are iconic! The geniuses behind the black loafer/white sock combo 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.

Ellis Penny Loafers

Take 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 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.

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 in all day. 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 it’s also one of the most consistent and reliable in terms of style. The company makes shoes that feel as good as they look, and at great prices, too.

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, minimalist 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 offers a wide variety of designs, like this dragonfly jacquard weave that’ll put a little pep in your step.

Why we love this brand: Taft is for people who aren’t afraid to stand out from the crowd. The brand has a vast assortment of funky prints that make getting dressed—even if you’re wearing a simple suit—a 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 that never detracts from the brand’s sophistication. Take these loafers, for instance—fun, modern, and fresh, but with polished leather and a Prada logo that still announces its elevated status in the world of fashion and footwear.

What to Look For

Unlike with a dressier pair of shoes, like oxfords or derbies, there aren’t any hard-and-fast rules you should follow when it comes to choosing loafers. Think of them as your sneakers’ classier older brother: They can hang out on a casual day, but they’re ready to tidy up your outfit and take you to the office, too.

If you want to get the most wear out of your loafers, look for something that’s both versatile and comfortable—obviously. Versatility that allows you to wear them 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 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 their style, quality, and comfort. Moreover, these are best-selling loafers from brands that our readers know and love.

How to Style Loafers

We’re living in an era in which 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.

Frequently Asked Questions

What is the difference between Blake stitching and Goodyear welting?

Aside from being handsewn, a Blake stitch and a Goodyear welt are the two most common kinds of constructions for a loafer. Blake stitching refers to the upper of the shoe being stitched directly onto the sole, with the insole and outsole attaching via a single-stitch method. Goodyear welting refers to stitching the shoe's upper to the welt, filling the sole with cork, and then stitching the welt to the outsole—in this method, the upper is not directly stitched to the sole.

Blake stitching, overall, allows more flexibility to the wearer. However, if you're going for longevity, a Goodyear welt allows a new sole to be replaced on the bottom of your shoe. Some buyers prefer the comfort of a Goodyear welt, too.

Are loafers worth investing in?

If you invest in loafers, you'll see time and time again why they're worth any amount of money. As you can see from the options above, there are plenty of great, affordable options, but don't be too quick to shy away from the more expensive ones, either. A loafer is a great, versatile dress shoe, so if you have a go-to pair that's built to last, you can feasibly where it just about anywhere, forever.

Top Loafer Brands and Styles

We love every pick on this list, or we wouldn't be recommending them to you. But, that being said, we definitely have our favorite favorites.

• For a beloved, infallible classic, there's no going wrong with G.H. Bass' iconic Weejuns.

• Here at Esquire, we can't get enough of Tecovas, and that goes for the brand's simple, stylish loafers, too.

• We've also waxed poetic before about how damn great the Doc Martens on this list are.

• And if you want something cool and luxurious—well, a thick-soled Prada shoe is hard to beat.

Shop More of Our Favorite Essentials

• Love leather loafers? We do, too. But for summer, you might want to grab a pair of breathable leather sandals, just in case.

• For a complete guide on dress shoes ranging from loafers to monk strap shoes, check out our ultimate dress shoes list.

• And, of course, no dress shoe is complete without an apt dress sock.

Why You Can Trust Esquire

We’re not about saying how great things are if they aren’t actually great. Every product in Esquire’s roundups is carefully chosen 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 tried, tested, and loved, along with options that the rest of our stylish colleagues here at Esquire prefer for their own everyday wear, whether that means going into the office or out to the bar. We love some of these styles so much, we’ve even endorsed them.

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 care (possibly too much!) about this sort of stuff, this is the place to be.

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