10 Comfortable Dress Shoes That Don’t Compromise on Style

G.H. Bass is the OG of the penny loafer—one that's made many of our lists here at Esquire. The brand's beef-roll-style loafer is iconic. Though you can go for the standard shape, we like this tassel add-on for something a little edgier. The shoe features a leather upper, moc stitching around the toe, and a heel tap. It comes in medium and wide widths—and a couple of other gorgeous colors, too.These best-selling shoes are crafted with a comfy, durable, soft leather inside and out. They're made with a Goodyear welt, making them easy to fix up and maintain when you need to. They have an easy look that pairs well with anything from denim to wool to silk. And thanks to their impeccably chic, thin laces, you can adjust the fit to your foot as needed. This pair really stood out to us because of its hard-wearing details and the natural look and feel that will only get better with age.Advertisement - Continue Reading BelowYou might be tempted to believe that "Comfiest Cap-Toe Oxfords" is an oxymoron, and we understand. A comfy leather oxford is hard to come by, due to the narrowed toe and closed lacing system. But these get pretty damn close. You will have to break them in, but it doesn't take forever, and there is more room in the foot than you might expect. It's a cap-toe oxford with a sleek, pairs-with-everything look. The insole is extra cushioned for maximum comfort, and because the leather is so flexible, reviewers say there's minimal creasing.Astorflex is a reliable choice for dress shoes that are solidly middle-of-the-road: not too dressy, not too trendy, and not too expensive. The soft suede construction opens around the laces (that's what makes them derbies) with a flexible rubber outsole that doesn't stray from its vocabulary of understated elegance. They pair easily with a summery suit or a more business-casual fit, and on the comfort side, the rubber outsole minimizes shock and provides traction if you get caught in inclement weather.Advertisement - Continue Reading BelowWe at Esquire love a derby, but we also understand that cheaper ones tend to look cheap too. Hate that. Instead, if you're really going for it, a high-end, well-made derby can make all the difference. This Todd Snyder one has a high lug sole, which is a little more stylish than a super buttoned-up sole. From its high-quality craftsmanship to its versatility and ability to pair with almost everything in your wardrobe—our particular favorite is the jeans, blazer, and loafer trifecta—this shoe instantly elevates. And, yeah, it's very comfortable too.A brown suede derby is a little offbeat but still a classic alternative dress shoe, particularly good for summer weddings and linen suits. These stunners are made-to-order with a water-repellent suede and an almond-shaped toe that gives a clean, natural line to any dressed-up outfit. Plus, there's a steel shank inside for keeping a solid, stable base on a shoe that can sometimes feel precious. The quality and details are top-notch all around.Advertisement - Continue Reading BelowLoafers generally err on the side of comfortable, but some have a tendency to cut up your heels and pinch your toes. Tecovas loafers are not those loafers. These are made with a soft cowhide leather, a grooved tongue, and a padded interior. They're made to be easy to slip on and off (but only when you're trying to).Okay, hear us out. You may have heard that Docs are a pain in the ass to break in, and that's kind of true, but after you do break them in, these will be the comfiest shoes you own. Our experts note that they basically mold to your feet as you wear them, so the leather ends up feeling soft all around and the rubber adds just the right amount of bounce to lessen the impact of each step. They're also versatile and work just as easily as a casual-ish dress shoe as they do as a knock-around one.Advertisement - Continue Reading BelowFlorsheim is another OG in the dress-shoe world, with comfy picks like this "oxford" that's really a derby. The burnished finish of the leather upper gives the shoe a slightly vintage look, and the rubber sole offers arch support and traction when you hit the dance floor. The style comes in four colors and has a cushioned removable footbed with built-in heel support.Clarks has a rich history thanks to its beloved desert boots, but the brand also does dress shoes that are equally comfortable. Its Whiddon shoe is a sleek lace-up that has a slightly casual bicycle-toe design that works better for semiformal occasions than for a black-tie event. No need to worry about these hurting halfway through the night, either. A removable triple-layer insert has extra cushioning, heel support, and a breathable lining that helps wick away sweat if your feet start to heat up mid-party. They obviously, however, look comfortable. Do with that what you will.Advertisement - Continue Reading BelowWhat Do I Need to Consider When Choosing?When it comes to choosing any pair of shoes, prioritize your comfort. We can't tell you how often we've been in a pinching, too-narrow pair of shoes wishing we'd tried them on before buying.Of course, comfort varies from person to person, but you should pay special attention to the various widths and the kind of footbed it has. Does it have a padded insole and arch support? If so, the shoe is likely to be comfier, especially in the early days of wearing it, before it's broken in.Considering where and when you'll wear your shoes will also help you in the long run. Loafers, for example, are far more versatile and easy to dress up and down than oxfords. A slip-on shoe is the better choice if you need to get in and out of them quickly (e.g., if you're traveling). Other details, like the construction of your shoe, are important too. A Goodyear welt adds some water resistance that a Blake construction doesn't.Color and material are other essential considerations in picking your perfect pair of shoes. Are you going to wear them in a place where the weather is inclement? If so, you may want to find a waterproof option. What about the dress code for the event you're RSVP'ing to? If you're looking for dress shoes for day-to-day wear, hey, dealer's choice on the color, but if you're attending, say, a black-tie wedding, you're going to want a more traditional hue like black.How Do You Clean Dress Shoes?If your dress shoes come with cleaning instructions or you can find them on the brand's website, follow those. But if you find yourself stuck with mud or dirt caked on your shoes and have no clue how to clean them, keep reading.Start by wiping your shoes down with a dry cloth to see how much dirt and debris you can clear. If the dry method doesn't do it, a small mixture of warm water and gentle soap should remove the rest of the dirt. Use a soft cloth to apply it, then if it looks like the shoes need it, apply a little leather conditioner at the end to keep the uppers supple. Remember to let them air-dry completely, and feel free to stuff them with newspapers or put them on a shoe tree to help collect extra moisture while maintaining their shape.Advertisement - Continue Reading BelowDo I Need to Break In Dress Shoes?We're going to level with you: Even comfortable dress shoes have to be broken in. High-quality shoes should be durable, which means leather that's substantial enough that it can form to your feet as you wear them.Once they're properly broken in, they'll fit like your favorite socks. And we know what you're thinking: Okay, but how can I do this quickly and without pain? While there's no magical solution, our experts recommend that you wear them around the house as often as you can—pace the halls and dance in the kitchen—and whatever you do, make sure you purchase them well ahead of an event like a wedding so you're not miserable come the big day.Why You Can Trust EsquireWe're not going to say something is great unless it's actually great. Every product in Esquire's roundups is carefully chosen by our fashion and e-commerce teams.When it comes to dress shoes—especially ones that emphasize comfort—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 endorse for their own wear. We've had to go through a lot of trial and error, and these comfortable dress shoes are the ones that are simply the best.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 tastes 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 about this sort of stuff, this is the place to be.