The 8 Most Stylish Types of Shoes For Men

Dave Bowden

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Types of Shoes For MenIf you spend even half as much time as I do trolling the aisles of department stores and menswear shops (note to self: get more hobbies), you may have noticed that the sheer number of men’s shoes is kind of overwhelming.

Every season, shoe stores release new models that come in a wide range of colors, styles, toe shapes and construction.

And, inevitably, every few months I find myself unable to resist buying another new pair, much to the chagrin of my (lovely, if long-suffering) wife.

But when I proudly go to display my new kicks on my (at this point comically large) shoe rack, something even more embarrassing becomes immediately apparent:

Even though I insisted that my most recent shoe purchase was utterly unique, when I put them on the rack, they usually look an awful lot like many of my other pairs.

Are they in better condition? Of course. But are they radically different? Well… not so much, to be honest. (Do not tell my wife!)

The Most Essential Shoes for Men

(There are fewer than you’d think…)

While shoe brands are always trying to innovate and add new flourishes to their models, the truth is that they can only do so much to distinguish them, because there really aren’t that many types of men’s shoes.

Sure, shoe addicts like me may continue to shell out money for new pairs each year, but if you really want to look sharp and stand out, all you really need to do is make sure you have a few key styles in your wardrobe.

In this post I’ll lay out the eight most stylish types of shoes for men, explain how you can get the most out of each style, and give you a few suggestions about which ones to buy if you want to look your best.

Types of Shoes For Men

The 8 Most Stylish Types of Shoes for Men

A Round Up of Must-Have Men’s Shoe Styles

Types of Shoes For Men

1. Wingtips

Types of Shoes For Men

Also called “brogues,” wingtips are among the most versatile (and thus, often the most worn) shoes in any man’s wardrobe.

One of the biggest benefits of wingtips is how perfectly they skirt the line between “dressy” and casual.

A sleeker pair with a well shaped toe can work just fine with a business or wedding suit, while a more casual pair – like the thick-soled Beckett Simonon Kents or the suede M.Gemi Idros – can help take a basic sweater-and-jeans outfit next level.

A Few to Try:


2. “Dress Shoes”

Types of Shoes For Men

That’s not a technical term, of course, but there are numerous shoe styles that are formal or “dressy” enough to wear on occasions that call for a suit, like weddings, funerals or job interviews.

As mentioned above, some brogues could be considered dress shoes, but generally speaking dress shoes are sharper and have a more pointed toe (just don’t go too pointy — you want to look refined, not like the genie in Aladdin).

In addition to the sharper shape, dress shoes tend to have fewer bells and whistles, like a thin outsole/welt and neutral laces and eyelets. As a rule of thumb, the sleeker a shoe looks, the dressier it is.

Pro Tip:

Keep in mind that dress shoes aren’t just for wearing with suits. Throw a pair on when you’re just rocking chinos and your favorite polo to instantly take your look from casual to “smart casual.”

A Few to Try:

Deep Dive:

3. Boat Shoes or Loafers

Types of Shoes For Men

Maybe the most classic warm weather staple of all time, the boat shoe evokes thoughts of John F. Kennedy effortlessly rocking a pair of Ray Ban wayfarers and sailing off the shore of Nantucket. Loafers, meanwhile, give you a similarly laid back (though admittedly more landlocked) vibe.

When you need something more casual than brogues but a little more grown up than sneakers, boat shoes or a comfortable pair of leather loafers are the perfect choice.

A Few Loafers Shoes to Try:

A Few Boat Shoes to Try:


Types of Shoes For Men


4. Sneakers

Types of Shoes For Men

Whether you’re running a few quick errands or just out having a casual drink with friends, sometimes you just want to wear sneakers, you know?

Sneakers long ago developed a culture unto themselves, and it’s pretty easy to find yourself intimidated or overwhelmed by the sheer volume and variety of shoes on the market.

Fortunately, they’re also a pretty easy pair of shoes to nail. Just keep it simple and look for one classic color (white, black, grey and blue are always safe choices), few labels, and a bit of contrast coming from the sole, laces, eyelets or all of the above.

A Few to Try:


5. Desert Boots/Chukkas

Types of Shoes For Men

When the weather gets too cold for your boat shoes or loafers, swap them out in favor desert boots or chukkas. The preferred footwear of everyone from Steve McQueen to James Bond, these boots scream “casual but classy.”

From about September to December, and then again from March to May, you could easily go weeks without having to wear a different kind of shoe (and I have to admit I sometimes do).

Clark’s offers one of the most classic, can’t miss pairs, as does Johnston & Murphy, but I prefer a style with a slightly sharper toe shape, like the ones pictured here from Alberto Fellini.

A Few to Try:

Deep Dive:

6. Suede Bucks, Brogues or Derbies

Types of Shoes For Men

Falling somewhere in between leather wingtips/brogues and boat shoes/loafers, suede shoes are a great way to stand out and add a little flair to your look, without going full peacock.

They’re a great way to make denim look a little more dressed up (though if you want a more rugged look, I’d suggest pairing your jeans with boots), and can also work well with chinos and casual pants.

If, like so many of us, you work in a business-casual office, suede bucks are a great way to look put together and respectable without crossing the line into stuffy or boring.

A Few to Try:


7. Double Monk Straps

Types of Shoes For Men

Double-monks came back hard a few years ago and haven’t gone away.

Named for the small buckles they use in lieu of traditional laces, monk straps tend to look a little more stylish and refined.

You can wear them in pretty much any situation where you’d normally wear dress shoes, or to elevate an otherwise casual look where you would normally suede bucks or chukkas.

A Few to Try:


8. Dress Boots

Types of Shoes For Men

Chukkas are great, but you can’t really wear them with a suit or a more formal outfit.

If you work in a formal office or frequently find yourself wearing a suit in cold-weather climates, you might want to consider a pair of boots that have the refined leather and sleek toe shape of a dress shoe, but run all the way up to your ankles.

A Few to Try:

J&M

Types of Shoes For Men

More Details ➤


Wrapping Up

Types of Shoes For MenNow that you know which shoe styles are most likely to help you look sharp and stand out, you’ll have a better idea of what to look for next time you’re trolling the department store? (No? Still just me? Well, I tried.)

Of course, while shoes are important, they’re still only one piece of the overall men’s style puzzle. If you really want to learn how to look great and out-dress the other guys, you need to know how to nail the details—all the details.

Enter your email address below and I’ll send you a checklist outlining the Nine Details You Need to Nail to step up your style and put both your best foot and your best face forward.

Types of Shoes For Men
The (handsome) devil is in the details

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Types of Shoes For Men

Further Reading ↓
From Irreverent Gent:
Other Takes on Must-Have Types of Shoes:

4 thoughts on “The 8 Most Stylish Types of Shoes For Men”

  1. Good list. I’ve been looking for some leather sneakers. Never would have thought to look at Suit supply, but those are pretty slick.

    • I know, right? I actually love Suitsupply’s casual clothes. They’re a bit pricey, but the style and quality are both a cut of above what you normally find in mall brands.

  2. Dave, question for you: are boat shoes ok to wear to the office? My office is super casual and I feel like dress shoes would be out of place, but I don’t like doing the sneakers look when I’m at the office. What do you think?

    • Hey Jake. Unless your “office” happens to be sea-based, then boat shoes at work are a big no for me. Why not go for another casual style like the suede bucks I recommend above? They’re not nearly as stuffy as dress shoes, but look more put together and business-like than sneakers.

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