The first two features you should look for in the best barefoot dress shoes are a roomy toe box and little to no heel drop. Better for your feet. More comfortable in the long run. You get it.

And now that the podiatrists are happy, let’s talk style. Easy, breezy, elevated style.

My top five barefoot-shoe picks embody those attributes with their quality materials, generous construction, and low-profile silhouettes. Although not all pairs feature completely flat soles, I’ve deprioritized those with anything even close to resembling a prominent heel drop.

Business casual loafers. Resort-ready slip-ons. If they’re handsome, comfortable, and just dressy enough, you’ll find them right down there in my tidily curated list of the five best barefoot dress shoes for men.

Key Takeaways 

To find the best barefoot dress shoes for men, I began by researching dozens of pairs and their materials, construction, customer reviews, photos, and more. The resulting five are the best of the best across a range of categories, from travel-ready footwear to happy-hour stunners and everywhere in between. My top overall pick is Oliver Cabell’s oh-so-traditional Penny Loafer HB. On its heels in the budget-friendly corner is Mitvrs’ Slip-On Driving Shoe.

Why they’re great: These timeless, full-grain leather loafers from Oliver Cabell feature a roomy toe box, minimal heel drop, and class — just so much class. Hand-stitched in Portugal, these classic statement-makers are made to last and will serve you well whether you’re gearing up for the office or for a casual coffee date.

Who are these for? If you’re looking for that one pair of barefoot dress shoes for every occasion, it’s nearly impossible to go wrong with these loafers.

Flaws but not deal-breakers: The most comfortable, podiatrist-recommended barefoot dress shoes will have noticeably wide toe boxes and zero heel drop. The problem? A lot of them are… well, ugly. Oliver Cabell’s Penny Loafer HB doesn’t fully check those boxes, but it comes damn close and looks a lot more handsome while doing it.

Material: 100% Leather | Sole Material: Rubber | Sizes Available: 6–14 | Colors Available: 2

Why they’re great: Which brings us to Velasca’s Brugnon Tassel Loafers. Dandies, these. Made in Italy, these eye-catching loafers feature soft suede uppers, a calf-leather lining, leather soles, and handmade tassels. All of which translates to a remarkably durable shoe that can be dressed up or down.

Who are these for? The man who values quality, durability, tradition, style—and yes, bare feet.

Flaws but not deal-breakers: If your job or lifestyle requires standing all day (or at least a large chunk of it), then you’ll likely be better off with something like Vivobarefoot’s Ra III Oxford. But if it’s all about business-casual office attire, après-office escapades, and rooftop nightcaps, then these are all you.

Material: Suede Calf Leather | Sole Material: Leather | Sizes Available: 5–14 | Colors Available: 5

Why they’re great: Perhaps no two words better capture the spirit of unabashed leisure than “yacht” and “loafers.” Combine them? They wouldn’t dare. Except Aurélien did, and the Amsterdam-based clothing and footwear company’s take on the classic loafer is every bit as handsome as you’d expect. Roomy, unlined suede uppers keep things breathable and stylish while durable, boating-inspired rubber soles hold down the traction and comfort fort.

Who are these for? You don’t have to summer in Monaco to pull off a pair of suede loafers like this. You could just as easily pair them with some smart chinos and a knit polo on a leisurely Saturday afternoon in… not Monaco.

Flaws but not deal-breakers: Like some other top picks on my list, Aurélien’s Yacht Loafers won’t be the best fit for wide-footed guys who need fully open-toe boxes and completely flat soles. If you’re not in that camp, then it’s tough to beat the comfort that these loafers offer.

Material: 100% Leather | Sole Material: Rubber Latex | Sizes Available: 6–14 | Colors Available: 42

Why they’re great: Striking the right balance between casual, dressy, comfortable, and budget-friendly can be a tricky proposition for any shoe. And while Mitvr’s Slip-On Driving Shoes are far from perfect, they get the seamlessly elevated job done. The vented leather uppers will ebb and flow with the contours of your feet, and the footbed provides ample arch support — a welcome addition for flat feet.

Who are these for? These lightweight, inexpensive driving shoes are best for the casual guy who refuses to sacrifice style regardless of the occasion.

Flaws but not deal-breakers: Though Amazon reviews are largely positive, a handful of reviewers thought that the uppers on these men’s barefoot dress shoes were too thin and that the overall quality was lacking. No surprise considering this is a budget option.

Material: Leather | Sole Material: Rubber | Sizes Available: 7–13 | Colors Available: 16

Why they’re great: Remember those podiatrist-friendly barefoot dress shoes I was talking about earlier? Well, here they are. Not a single box is left unchecked when it comes to the Vivobarefoot Ra III Oxford. Wide toe box. Zero-drop heel. Leather uppers. Rubber soles. And lest we forget the dress shoe part of the equation, these cozy, roomy oxfords are office- and occasion-ready.

Who are these for? The guy who wants to look the part but is more concerned with comfort and foot health than turning heads or making sartorial statements.

Flaws but not deal-breakers: Look, I get it. These are some pretty specific-looking barefoot dress shoes. Kinda dad-like. Kinda sneaker-like. They’re not for everyone, but they damn sure are comfortable, and they’re more than capable of shepherding your bare feet through almost any occasion.

Material: 100% Leather | Sole Material: Rubber | Sizes Available: 7W–12W | Colors Available: 5

Buying Considerations for the Best Barefoot Dress Shoes

Size and Fit

The best barefoot dress shoes should have a wide toe box, little to no heel drop, and be made of materials that conform to the contours of your feet over time. Prioritize durable, comfortable shoes and—perhaps most importantly—remember that there’s no substitute for some old-school trial and error.

Style

Pulling off the casual dress shoe look is an art, not a science—especially in the absence of socks. There’s a time and place for traditional derby shoes, dressed-up boots, and other standard fare. That time is not now, and that place is not here. When it comes to the top barefoot dress shoes, stick with leisure-adjacent designs like loafers, slip-ons, and other laceless specimens.

Material

Regardless of whether you’re going for the true barefoot shoe experience or plan on wearing no-show socks, this is one type of dress shoe that demands comfort. And comfort, of course, starts with the materials used in the shoes’ construction. For the purposes of this list, I focused mainly on leather products. Shoes made of this timeless, elevated material are soft and forgiving and will conform to the contours of your feet over time.

How We Chose

As a fashion and grooming writer at FashionBeans, I compare, test, and research the products that make a gentleman a gentleman. If it can be worn, carried, or used in a way that elevates your look and feel, I’m into it.

For this review, I pored over trusted sources, customer reviews, materials, construction specifications, and my own experience to understand what makes the best men’s barefoot dress shoes. Some of my key considerations include:

Comfort: Not all men’s barefoot dress shoes are created equal. If you’re on your feet all day, for instance, then opt for a thicker rubber sole as opposed to a thin, dressy, all-leather one. If you’re a heavier guy, then you’ll need to lean into support and stability features first and foremost. For the purposes of this list, I made every effort to prioritize versatile shoes with wide-toe boxes and minimal to no heel drop.

Customer Reviews: I pored over multiple product reviews in search of both positive and negative throughlines to help inform my picks for the best men’s barefoot dress shoes.

Materials: Regardless of the shoe style, anyone can pull off a dressy look with enough confidence and sartorial wherewithal. That said, the majority of the top barefoot dress shoes on this list are made of some form of leather. Why? Not only will it seamlessly ebb and flow with the contours of your feet over time, but it’s also got an impressive shelf life and can elevate any outfit.   

Why Trust Us?

Kelly is a long-time writer for FashionBeans and an all-around shoe enthusiast. In addition to hours of independent research, Kelly relied heavily on his own experience to find the best barefoot dress shoes out there. He’s also written prolifically on the topic of footwear, covering the most comfortable men’s walking shoes, the best dad shoes, cowboy boot brands, and comfortable dress shoes, to name a few.

To substantiate that experience, he researched dozens of men’s barefoot dress shoes, examining materials, construction, customer reviews, and his own closet to pick the best of the best. If there’s a stranger to trust for footwear advice, it’s Kelly.

Final Verdict 

Beyond having roomy toe boxes and little to no heel drop, the best barefoot dress shoes embody easy, breezy, elevated style. My top overall pick based on its ample toe box, timeless style, and barefoot-ready silhouette is the venerable HB Penny Loafer from Oliver Cabell.