The 10 Best Men's Dress Shoes

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This wiki has been updated 42 times since it was first published in April of 2015. Even the most dashing outfit can be undermined by tattered or boring footwear. Fortunately for you, the men's dress shoes on this list will ensure that you always stand out — and feel great — whether you're on a date or a job interview. We've included styles that work well dressed up or down, and ranked them here by comfort, style, and durability. When users buy our independently chosen editorial choices, we may earn commissions to help fund the Wiki.

1. Magnanni Marco Monk Straps

2. Florsheim Montinaro Chukka Boot

3. Allen Edmonds Strand

Editor's Notes

February 10, 2020:

With certain styles never seeming to go out of fashion, like the Allen Edmonds Strand oxfords, it was important to us to keep things as current as possible, and for particularly dressy occasions, monk straps offer some of the best performance out there. They're easy to put on and take off, and they have a lot more character than a basic lace-up can offer. That's why we kept both the Magnanni Marco Monk Straps and the Anthony Veer Roosevelt II on this list.

What we did get rid of were the Johnston & Murphy Melton. J&M is a pretty reliable company, but these shoes were simultaneously a little too basic and total scuff magnets, so much so that few pairs seem to be able to make it from the factory to your doorstep in very good condition. We replaced those with a pair representing one of the hottest styles around from one of the oldest American companies in the Florsheim Montinaro Chukka Boot. They look just as good with a suit as they do with jeans and a leather jacket, and their memory foam footbeds make them incredibly comfortable, as well.

4. Cole Haan Pinch Tassel Loafers

5. Cole Haan Cambridge

6. ZRO Modern Oxford

7. Ecco Holton

8. Anthony Veer Roosevelt II

9. Asher Green Spectator

10. Bolano Brayden

Dance Like A Fool

If we're lucky, they have lights inside them that flash when we walk.

We go through a lot of shoe phases throughout our lives. Early on, we live in sneakers fastened to our feet by velcro. If we're lucky, they have lights inside them that flash when we walk. Then, we graduate to laces, though we usually remain in sneakers. Sandals and boots come and go with the seasons. At some point, though, even as young men, we encounter our first pair of dress shoes.

At around five years old, I got myself into my first suit, and I spent the bulk of the night dancing up and down the rooms of a fancy banquet hall, my eyes fixed on my footwear, fascinated by the way the shoes caught the light.

I became rather divorced from dress shoes in my later childhood years, my teens, and even my early 20s. It wasn't until I started dressing like a grown man from head to toe that the coverings for those toes became more important to me.

I soon realized that a good pair of dress shoes could tie together a whole outfit in ways that are mostly subtle, but that are certainly undeniable. It doesn't even matter if the rest of you is dressed up; any time you look down, you should feel that rush of completion, of accomplishment.

You'll notice that the shoes on our list are all derived from cowhide treated one way or another. They're either leather or suede, the former bearing a greater degree of reflective power, and responding better to polish. The soles, each of which bears a slight elevation for comfort and posture, are either leather, rubber, or wood with rubber gripping in the heel, providing better traction that shouldn't inhibit your ability to dance like a fool five-year-old, should you be so inspired.

Style By Style

I'm sure I'm not alone in this, but I've made some bad footwear decisions throughout my lifetime. I knew it when I made them, too. I'd get a pair of shoes I thought would be the coolest things in the world and realize very quickly that I looked ridiculous in them. Specifically, I'm haunted by a pair of bright red Vans with a large black skull and crossbones on them. I don't know what I was thinking.

Shoes with a more pointed toe, though rounded, are very much more in vogue than the flat-front styles that ran the shoe show back in the 1990s and early 2000s.

That said, there are people out there for whom those shoes would have worked. I was young, and I was still learning who I was and how I wanted to express my sense of self. As you take in the options we've provided on our top ten list of men's dress shoes, it'd be a good idea to know a little bit about yourself, about your current wardrobe, and even about the look or looks to which you aspire.

If you're the consummate casual dresser, you aren't prohibited from enjoying the occasional dress shoe. In fact, sporting a couple of these ten styles with a nicer pair of jeans creates one of the smarter casual looks available in modern menswear. It says that you're so casual about being casual that you almost inadvertently make it look nice. The suede shoes on this list, in particular, are tailor-made for dressing up or down as you see fit.

For the businessmen among us, the boys who have themselves in suits on a daily basis, your decision will be based as much on color and shape as anything else. Shoes with a more pointed toe, though rounded, are very much more in vogue than the flat-front styles that ran the shoe show back in the 1990s and early 2000s.

Then, there's a sort of intermediary between the more causal look and the smart business attire with a hint of high fashion to it. These are the shoes on our list that fit better in a loafer category than anywhere else. Their number one priorities are comfort and convenience. You shouldn't need a shoe horn to get into them, they require no tying, or strapping, or buckling, and their appearance screams of the easy life.

A Well-Adorned Walk Through History

Until the late 16th century, footwear rarely meant more than strips of leather or cloth tied or strapped to one's feet. The sandal styles popular in Mediterranean climates like Greece and Italy didn't make a lot of sense in the colder rainy filth of early modern England, France, and Germany.

Every once in a while, a new style element makes its way onto the wheel, but rarely in the realm of dress shoes, where a more conservative bent has reigned for centuries.

In the courts of those countries, however, footwear evolved into the 17th century to include bows, buckles, and even heels. Later in the century, as war tore through Britain and the rest of Europe, military fashions began to inform the design and popularity of men's footwear.

The periods in Europe of Enlightenment, as well as the French Revolution, popularized a more agrarian aesthetic, as the power and importance of the common citizen took on a whole new meaning. This was the first wave in which the aristocracy looked to the styles of the peasantry for fashion inspiration, a trend that would last on into today.

More recently, the fashions that developed in the Enlightenment and post-Enlightenment periods seem to swirl around one another, with one version of a shoe popular for about a decade or two and another one taking its place thereafter, only to be supplanted itself by a third as the wheel of footwear turns round and round. Every once in a while, a new style element makes its way onto the wheel, but rarely in the realm of dress shoes, where a more conservative bent has reigned for centuries.

Daniel Imperiale
Last updated by Daniel Imperiale

Daniel Imperiale holds a bachelor’s degree in writing, and proudly fled his graduate program in poetry to pursue a quiet life at a remote Alaskan fishery. After returning to the contiguous states, he took up a position as an editor and photographer of the prestigious geek culture magazine “Unwinnable” before turning his attention to the field of health and wellness. In recent years, he has worked extensively in film and music production, making him something of a know-it-all when it comes to camera equipment, musical instruments, recording devices, and other audio-visual hardware. Daniel’s recent obsessions include horology (making him a pro when it comes to all things timekeeping) and Uranium mining and enrichment (which hasn’t proven useful just yet).

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