<p class=”body-text”>Go for a <a href=”https://www.esquire.com/style/mens-fashion/a43307082/dr-martens-loafer-review/” target=”_blank”>loafer</a>, an <a href=”https://www.esquire.com/style/mens-fashion/g46867536/best-oxford-shoes/” target=”_blank”>oxford</a>, or a <a href=”https://www.esquire.com/style/mens-fashion/g43124911/best-derby-shoes-for-men/” target=”_blank”>derby</a> depending on taste and formality restrictions. Whatever your choice, proper <a href=”https://www.esquire.com/style/mens-fashion/a60878857/boat-shoe-trend-2024/” target=”_blank”>footwear</a> shouldn’t cramp your feet or style. Burn your sneaker-dress-shoe hybrids and cheap faux-leather, none of that stuff is on the list. Yes, that means a few of these may still require a break-in period, but all these models have small startup times. </p><p class=”body-text”>Before the next wedding, <a href=”https://www.esquire.com/style/mens-fashion/a45210983/cocktail-attire-for-men/” target=”_blank”>cocktail party</a>, or fancy work shindig pops up on the calendar, check out our picks below. Your feet will thank you.</p>” data-next-head/>
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Comfiest Loafer
G.H. Bass Larson Lug Weejuns Loafers
Pros
- Comfort of a moccasin
- Excellent lug detailing
Cons
- Runs a little big
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 lug sole for something a little edgier. 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.
| Colors | 3 |
|---|---|
| Sizes | 7-14 |
| Materials | Leather, EVA outsole |
Comfiest Iconic Derbies
J.Crew Ludlow Derbys
Pros
- Sturdy shoe overall
- Versatile
Cons
- Some buyers report squeaking
These best-selling shoes are crafted with comfy, durable materials like Italian leather and a cork insole that molds to your feet. 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.
| Colors | 2 |
|---|---|
| Sizes | 7-14 |
| Materials | Leather |
Comfiest double monk shoes
Thursday Boots Saint
Pros
- Shock-absorbing insoles
- Wide size range
Cons
- Some buyers say they run a little small
A good double monk shoe—like this exceptionally stylish and comfortable pair from Thursday Boot Company—is a great dress shoe option that feels just a bit different than your other dress shoes. It’s a little more pulled together and never looks messy with its lack of laces. 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 and sturdy stitching. They fit up to size 16.
| Colors | 2 |
|---|---|
| Sizes | 6-16 |
| Materials | Leather, rubber |
Best Luxury Dress Shoe
Gucci Horsebit Loafers
Pros
- Iconic design
- Soft but sturdy leather upper will form to your foot with wear
Cons
- Expensive
We at Esquire love the Gucci Horsebit 1953 Loafer, but we also understand it can be a little low profile for some or feel just a little too trendy. This loafer has a higher, more substantial sole, which is as classic as it gets. 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 | 8-13 |
| Materials | Leather |
Most comfortable suede dress shoes
Beckett Simonon Dean Oxfords
Pros
- Rubber heel caps prevent slipping
- Water-repellent suede
Cons
- Shipping can take some time
A brown suede oxford 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 and come in five colors. They’re made with a water-repellent suede and an almond shape 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.
| Colors | 2 |
|---|---|
| Sizes | 7-14 |
| Materials | Suede, rubber |
Comfiest Black Penny Loafers
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.
| Colors | 3 |
|---|---|
| Sizes | 6.5-15.5 |
| Materials | Leather, rubber |
I-Require-Comfort-Above-All-Else Dress Shoes
Clarks Whiddon Shoes
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 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.
| Colors | 5 |
|---|---|
| Sizes | 7-15 |
| Materials | Leather, rubber |
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.
Why You Can Trust Esquire
We’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.
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