The 17 Most Comfortable Dress Shoes, Tested by Style Editors

Clarks Whiddon Shoes

Pros

• Affordable
• Removable padded insole
• Available in wide widths

Cons

• Some buyers say they run a little tight

Clarks has a rich history thanks to its beloved desert boots, but the brand also does dress shoes that are equally as comfortable. Its Whiddon shoe is a sleek lace-up that has a slightly casual bicycle toe design that works better for semi-formal occasions than 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.

One customer said:"Easily the best pair of Clarks I've had so far. Well made, elegant, and they have an extra thick and heavy sole which makes them even more comfortable."

Florsheim Medfield Shoes

Pros

• Fit true to size
• Great all-weather traction
• Available in wide widths

Cons

• Some buyers don't like the burnishing

Florsheim 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.

One customer said:"This shoe is amazing for the price—looks terrific, made well, and seems comfortable enough for standing and walking for long periods of time."

Magnanni Federico Shoes

Pros

• Extra cushioning on the insole
• Minimal creasing
• Butter soft leather

Cons

• Only available in one color

You can tell from the look of the smooth, buttery leather that these shoes will fit like your best pair of gloves. It's 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.

One customer said:"These are easily the best shoes I have ever owned. The style is so very classic but modern at the same time. They were so comfortable that I didn’t have to break them in at all. I wore them all day right out of the box to my son's wedding and never had a complaint."

Samuel Hubbard Tipping Point Shoes

Pros

• Breathable leather lining
• Removable memory-foam footbed
• Comes in medium and wide widths

Cons

• Sells out quickly

The slightly thicker sole on these Samuel Hubbard wing-tip derbies is the first sign that these were made for all-day comfort. But that doesn't take away from the aesthetic of the classic broguing in the leather upper. Inside, a triple-density memory foam insole adds to the overall plushness and can be popped in and out as needed. Guys who have bought and worn them say there's no break in period and if you need a dress shoe with arch support, these are the ones.

One customer said: "I've worn Ferragamos for years; but, I needed something less constrictive, with a wider width ... because I’m now spending more time than ever before wearing a suit (and therefore needing to wear dress shoes all the time). The Hubbard Tipping Points are exactly what I needed. They provide all-day comfort and allow me wear dress shoes every day without the experience being uncomfortable."

Tod's Penny Loafers

Pros

• Made from soft and durable quality leather
• Rubber outsole with embossed rubber pebbles for traction

Cons

• Pricier than other options

Loafers generally err on the side of comfortable, but some have a tendency to cut up your heels and pinch your toes. Tod's loafers are not those loafers. The brand put many of the same details from their beloved driving shoes into these penny loafers like the pebbled rubber sole for grip and the smooth and flexible leather upper.

One customer said:"The craftsmanship is outstanding, with high-quality leather that feels luxurious and durable. The fit is perfect, providing excellent comfort for long hours of wear. The elegant design is timeless and pairs well with both formal and semi-formal attire."

Thursday Boot Company Aviator Shoes

Pros

• Shock-absorbing insoles
• Blake stiching for flexibility
• Wide size range

Cons

• Some buyers say they run a little small

A good brogue like this exceptionally stylish and comfortable pair from Thursday Boot Company should be in every man's closet. Alongside the soft leather lining is a shock-absorbing insole that takes the pressure out of every step and is antimicrobial so it won't smell funky if your feet sweat. The outside is made for durability with premium leather, sturdy stitching, and waxed cotton laces that won't fray over time. What's also great about TBC is that they come in three colors and fit up to size 16.

One customer said: "The quality and fit of the shoe is top tier, if I had the need for every color of this shoe, I would definitely buy them all ASAP."

Gucci Horsebit 1953 Loafers

Pros

• Iconic design
• Soft but sturdy leather upper will form to your foot with wear

Cons

• Expensive

We're calling the Gucci Horsebit 1953 Loafer one of the official favorite shoes of Esquire. We've waxed poetic about several Gucci loafers but this version is worthy of another level of praise. From its high-quality craftsmanship to its versatility and ability to pair with almost everything in your wardrobe—our particular favorite is a jeans, blazer, and loafer trifecta—this shoe instantly elevates. And, yeah, it's very comfortable, too.

Mephisto Max Wingtip Derbies

Pros

• Very durable
• Shock-absorbing sole

Cons

• Pebbled leather isn't everyone's taste

The first word to describe Mephisto's wingtip derbies is durable. The stacked rubber sole with shock absorption is a solid choice for avoiding foot pain. If you plan to stand for hours, these will deliver just the right amount of support without feeling overly clunky. The textured full-grain leather upper is certainly a style preference, but a classic one—and there's a black version, too.

One customer said: "Outstanding and durable dress shoes—I've had mine for a decade and they are still going strong. Take care of them, they take care of you. After 12 hours my feet still feel great. Awesome product!"

Paul Evans The Newman Chukka Boot

Pros

• Hand-painted leather
• Comes in several colors

Cons

• Runs a full size large

Chukka boots can lean casual, but these high-gloss leather boots are as sleek and sophisticated as they come. The soles have been hand-painted to match the upper for a seamless look. The inside is also lined in leather, for even more softness for your hard-working feet. These come in five leather colors and three suede options.

One customer said: "I am constantly getting compliments when I wear these shoes. The color and design are incredible. This is my third pair of Paul Evans and are quickly becoming my favorite. The fit was perfect and they are extremely comfortable. You can't go wrong with the Newman Chukka! The experience of ordering and shipping are always excellent."

Beckett Simonon Leonard Monkstraps

Pros

• Rubber heel caps prevent slipping
• Available in five colors

Cons

• Shipping can take some time

Monkstraps are a little offbeat, but still a classic alternative to derbies or oxfords. These stunners are made to order and come in five colors. The temperature-regulating leather lining keeps your feet from overheating, and then there's a steel shank sandwiched between the inner and outer soles for added support while standing. The quality and details are top-notch all around.

One customer said:"I continue to be blown away by these shoes every time I wear them. The quality is simply outstanding. I was somewhat nervous about how these would hold up to standing at work for 10 hours a day but they are super comfortable. On top of the quality and comfort they just look great. Excited to wear these shoes for a very long time and add some other Beckett Simonon options to the lineup soon."

Alden Cordovan Plain Toe Bluchers

Pros

• Good-year welt stitching adds water resistence
• Wildly versatile design

Cons

• Pricier than other options

Sometimes the best dress shoe is the simplest dress shoe. Case in point, this plain-toe blucher. If your dressy occasion ends up being a soggy one, the good-year welt stitching around the sole will keep any bits of moisture out. The double leather soles are flexible and durable, and adds the right amounts of cushioning for comfy walking and dancing.

One customer said:"This is the perfect shoe: dress it up or dress it down. And, comfortable to boot!"

Banana Republic Oxford Shoes

Pros

• Great traction sole and flexible leather upper
• Waxed laces won't fray
• Comes in two colors

Cons

• Limited sizes available

Banana Republic is a reliable choice for affordable dress shoes. These so-called "oxfords"—the open construction around the laces means they're actually derbies—with a flexible rubber outsole don't stray from its vocabulary of understated elegance. They pair easily with a 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.

One customer said: "These dress shoes are super comfortable in the sole and have soft leather! Perfect fit, my husband is a size 10 and these are a solid 10."

Dr. Martens 1461 Mono Shoes

Pros

• Durable and long-lasting
• Can be dressed up or down
• Good traction

Cons

• May require a break-in period

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 a knock-around one.

One customer said: "These are my all-time favorite shoes; tough, comfy, pretty indestructible, and last for ages."

Stuart Weitzman Club Shoes

Pros

• Good arch support
• Available in two colors

Cons

• Can sell out quickly

These are super classy and a little unique, too, with a slightly squared-off toe. Wear them with everything from trousers to a suit. The stacked heel, padded insole, and rubber outsole are ideal for flat feet that need arch support—but it doesn't make them clunky or heavy. They're still very lightweight and flexible.​

One customer said:"I love that Stuart Weitzman is making men's shoes now, and these classic Oxfords definitely deliver. They're comfortable for all-day wear and go with everything I already have in my closet. They've become a staple in my wardrobe, and I reach for them anytime I need an elevated shoe."

Koio Arezzo Loafers

Pros

• An EVA sole keeps the shoe lightweight
• Made with sustainable materials

Cons

• Some buyers say they run too large

Chunky loafers are a more trendy take on a classic, but a style like this with its lug sole and classic penny loafer details makes the dressier pieces you pair these with feel more modern. Plus, the cushiony bottom adds plenty of shock absorbency. On a more practical level, the tight stitching between the sole and leather upper adds water resistance.

One customer said:"I put them on right out of the box and they looked and fit perfectly! I’m on my feet all day at work and so far so good going on 7 hrs! Love them."

Ferragamo Funes Leather Loafers

Pros

• Slip-on style is ideal for business travel

Cons

• Only comes in one color

The almond toe shape on these Ferragamo loafers up its dressiness level from a classic loafer. The rubber sole makes standing in these loafers more comfortable and they are available in three different widths, so if you like the narrower look but have a wider foot, pick accordingly. There's a note that they run large so you may need to size down a half size.

G.H. Bass Weejuns Loafers

Pros

• Available in multiple colors
• Comfort of a moccasin

Cons

• Not a lot of traction on the sole

G.H. Bass is the OG of the penny loafer—one that's made many of our lists here at Esquire. The brand's beefroll-style loafer is iconic. The shoe features a leather upper, moc stitching around the toe, and a stacked heel. It comes in medium and wide widths and a bunch of colors, too.

One customer said:"This is the only dress shoe I wear. G.H. Bass just knows what they're doing when it comes to timeless footwear that will last you for years, dare I say even decades? This style is classic, versatile, and incredibly durable. So basically, anything you could ever want in a shoe."

What 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 RSVPing 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 a shoe tree to help collect extra moisture while maintaining shape.

Do 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 it.

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.