The 17 Most Comfortable Dress Shoes, Tested by Style Editors
<p class=”body-dropcap”>Whether your dress shoe of choice is a <a href=” target=”_blank”>loafer</a>, an <a href=” target=”_blank”>oxford</a>, or a <a href=” target=”_blank”>derby</a>—proper <a href=” target=”_blank”>footwear</a> shouldn’t cramp your feet or style. Sneaker-y hybrids that have no business mashing up, options that look worn out quickly, cheap-looking stuff you’d swear was plastic and not leather—we’ve seen some pretty ugly dress shoes. This list doesn’t include any of them. From substantial stompers to sleeker styles with thinner soles and supple leather, all of them will cradle and support your feet without being overly stiff. Yes, a few may still require a break-in period, but that should be minimal. </p><p class=”body-dropcap”>Before the next wedding, <a href=” target=”_blank”>cocktail party</a>, or fancy work shindig pops up on the calendar, check out our 17 picks below. Your feet will thank you.</p>” data-next-head/>
Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.
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 semiformal attire.”
| Colors | 3 |
|---|---|
| Sizes | 6.5-15.5 |
| Materials | Leather, rubber |
Best Luxury Dress Shoe
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.
| Colors | 2 |
|---|---|
| Sizes | 5-17.5 |
| Materials | Leather |
Best for Arch Support
Mephisto Max Wing-Tip Derbies
Pros
- Very durable
- Shock-absorbing sole
Cons
- Pebbled leather isn’t everyone’s taste
The first word to describe Mephisto’s wing-tip 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!”
Best Dressy Boot
Paul Evans The Newman Chukka Boot
Pros
- Hand-painted leather
- Come in several colors
Cons
- Run 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 hardworking 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 experiences of ordering and shipping are always excellent.”
| Colors | 5 |
|---|---|
| Sizes | 5-16 |
| Materials | Leather |
Best Monk-Strap Dress Shoes
Beckett Simonon Leonard Monk Straps
Pros
- Rubber heel caps prevent slipping
- Available in five colors
Cons
- Shipping can take some time
Monk straps 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.”
| Colors | 5 |
|---|---|
| Sizes | 7-14 |
| Materials | Leather |
Best Goes-with-Everything Dress Shoe
Alden Cordovan Plain-Toe Bluchers
Pros
- Goodyear-welt stitching adds water resistance
- 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 Goodyear-welt stitching around the sole will keep any bits of moisture out. The double-leather soles are flexible and durable and add 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!”
| Colors | 2 |
|---|---|
| Sizes | 7-13 |
| Materials | Leather |
comfiest new dress shoes
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 don’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.”
| Colors | Brown |
|---|---|
| Sizes | 5-14.5 |
| Materials | Leather |
Sleekest Loafers
Ferragamo Funes Leather Loafers
Pros
- Slip-on style is ideal for business travel
Cons
- Only come in one color
The almond toe shape on these Ferragamo loafers up the dressiness level from a classic loafer. The rubber soles make 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.
Comfiest Loafer
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 beef-roll-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.”
| Colors | 7 |
|---|---|
| Sizes | 7-12.5 |
| Materials | Leather |
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 on a shoe tree to help collect extra moisture while maintaining their 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 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.
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