The 17 Most Stylish Types of Men’s Shoes

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If you spend as much time as I do obsessing over menswear (and for the sake of your sanity, I really hope you don’t), you’ve probably noticed that there are about a bajillion different pairs of shoes on the market. 

At least, that’s certainly how it feels

Every season, my local shoe store trots out a ton of new models in a wide range of colors, styles, toe shapes and construction, resulting in hundreds – if not thousands – of new shoes to choose from. 

But while the top brands are always trying to innovate and add new flourishes to make their shoes feel fresh, the truth is that, fundamentally, there really aren’t that many different types of shoes for men. 

To help you step up your shoe game, in this post we’ll break down the most stylish, fundamental and essential types of men’s shoes, and show you how to get the most out of each type of shoe. 

The Most Stylish & Dapper Men’s Shoe Styles

Breaking Down the Most Essential Shoes Every Man Should Own

The Most Stylish Types of Dress Shoes for Men ↓

Oxford Shoes

Oxford shoes
[Image: Beckett Simonon]

Oxfords are arguably the most essential type of dress shoe in the modern man’s wardrobe. 

(Which is ironic, because their origin is old as sh*t. They’re named for the UK’s Oxford University, where they originally became popular way back in the Victorian Era of the 19th century.) 

Shoe nerds like me geek out on oxfords thanks to their closed lacing system, which means the eyelet tabs that the laces pass through are sewn on underneath the shoe’s vamp. 

But for most guys, the reason oxfords are so essential is because they’re arguably the most sophisticated and formal shoes a man can own. 

Their sleekness and simplicity make them perfect for pairing with formal suits like a business suit or tuxedo, and great for formal occasions like weddings, funerals, fancy first dates or important business meetings.  

I wore a pair of plain toe black oxford shoes when I got married a few years back, and have since worn the same pair to a friend’s engagement party. 

Sharp Selections: 

Derby Shoes

Man wearing chinos and derby shoes
[Image: StepPro / Shutterstock]

If oxfords are the most essential of all the different types of dress shoes, derbies are a close second place. 

While they’re similar to oxfords in a lot of ways, the key difference is that derbies have an open lacing system, meaning the eyelets for the laces are sewn on top of the vamp, rather than underneath. 

The result is a slightly more casual look, but make no mistake: 

This is still one of the most sophisticated shoe types you can find, especially if you opt for a well made pair with a leather sole (as opposed to a thicker rubber sole), which keeps them looking sleek and refined. 

While derbies might not cut it at super fancy black tie events, which call for the absolute most formal clothes, they can be paired with pretty much every other type of formal attire, including business suits. 

Plus, derbies are arguably more versatile than oxfords, since their (slightly) more casual nature makes them perfect for pairing with the kind of sharp, smart casual outfits you wear outside of the office. 

As a rule of thumb, if you want a pair of super fancy shoes you can wear for a special occasion, opt for oxfords. 

But if you want a more versatile shoe you can pair with casual attire for everyday wear, go with derbies. 

Sharp Selections: 

Monk Strap Shoes 

man wearing jeans and double monkstrap shoes
[Image: Allen Edmonds]

Monk strap shoes refer to shoes that forego laces in favor of a single piece of leather, which is strapped across the top of the shoe and held in place with one or more buckles. 

There are two main varieties of monk shoes: 

Single monk straps, which have just one (usually slightly bigger) buckle, and the more popular double monk straps, which (you guessed it) have two. 

And while there is technically a third kind – triple monks – I wouldn’t recommend them, partially because they’re rare and pretty hard to find, but also because, in my humble opinion, the third buckle is just overkill. 

Sharp Selections: 

Brogues / Wing Tips

man wearing jeans and wingtip shoes
[Image: Benjamin Rascoe / Unsplash]

Brogues aren’t really their own kind of shoe in the same way that oxfords, derbies and monk straps are, but they’re very much worth knowing about.  

Rather than being defined by their construction and lacing system (or in the case of monks, lack thereof), brogues are defined by the decorative perforations that dot the shoe. 

As such, you can actually find oxford brogues, derby brogues and even monk brogues, so I’d argue that it’s more of a style of shoe than a distinct type. 

But it’s worth calling out, since brogues have a more bad-ass origin than your standard pair of dress shoes:  

They date back to British hunting parties, who would poke small holes in the leather uppers of their shoes to release water while they trekked through puddles and bogs. 

Sharp Selections: 

Essential Types of Loafers for Men ↓

Penny Loafers 

Man wearing chinos and penny loafers
[Image: Miad Vosoughi / Shutterstock]

One of the most common types of loafers, Brooks Brothers refers to penny loafers as “all in all just about the most versatile shoe you will ever slip on.” 

And they’ve got a point. 

What makes penny loafers so versatile – and so essential – is that they can be dressed up or down, and take you just about anywhere. 

Depending on the toe shape and the quality of the material used (usually leather or suede), they can be paired with a suit and worn to formal events, or paired with jeans to punch up your casual style. 

Oh, and in case you’re wondering about the name, it’s an old school reference to a time when a single penny was actually useful: 

Back in the day, a phone call on a pay phone cost two cents. Guys would slip one penny into the tongue of each loafer, so that they always had enough money to make an emergency phone call if they had to. 

Sharp Selections: 

Bit Loafers 

man wearing bit loafers
[image: Beckett Simonon / Instagram]

Bit loafers look a lot like penny loafers, only instead of a single strap across the top of the shoe with a hole that fits a penny, they have a metallic bit that’s similar in shape to a horse bit. 

The extra metallic detail gives bit loafers a slightly more sophisticated look and feel than other loafers, which many people think of as one of the more casual men’s shoe styles. 

They’re a good alternative to penny loafers if you want to add a dapper detail that will help you stand out, and a great option for more dressed up summer occasions, when you’re going for a look that’s casual, but well put together. 

Sharp Selections: 


Tassel Loafers 

multiple tassel loafers
[image: Beckett Simonon / Instagram]

Whereas the two loafers above can be worn by many different types of men, tassel loafers tend to be reserved for fashion-forward clothes horses. 

The addition of the leather tassels lend these loafers a distinctly dashing, European, devil-may-care vibe.  

They remind me of something that could (and almost certainly has) been worn by Italian fashion aficionados like Lapo Elkann, the heir to the Fiat care fortune who’s well known as one of Italy’s most dapper men.  

Sharp Selections: 

Driving Shoes  

Man wearing chinos and drivers
[Image: Wolf & Shepherd]

While you don’t see tassel loafers as often on this side of the pond, drivers are s little more common. 

And much more versatile. 

Driving shoes are distinguished by their rubber soles, which is designed to help your foot grip the pedal when you’re behind the wheel. 

But the same features that makes them easy to drive in also makes them pretty comfortable to walk in, making drivers a great everyday shoe. 

I have a couple different pairs of drivers, and come spring I usually ditch the socks and make them my go to for running errands or going for walks with the family.

Sharp Selections: 

Other Types of Casual Shoes for Men ↓

Athletic Shoes 

athletic shoes surrounded by weights
[image: Alexandra Tran / Unsplash]

Nowadays sneakers have been elevated to the point where they’re practically business wear (or at least business-casual). 

So when I say athletic shoes, I mean shoes you can actually wear while working up a sweat.

Whether you prefer basketball shoes, tennis shoes, cross trainers or any other specific type,  every man needs a good pair of athletic shoes from performance-focused brands like Nike, New Balance or All Birds.

Sharp Selections: 

Casual Sneakers 

Man wearing white sneakers
[Image: cottonbro / Pexels]

Casual sneakers can refer to everything from the type of crisp white sneakers that are basically wardrobe essentials to more athletic-looking shoes that don’t actually see any game action. 

After all, if you want to keep your sneakers clean enough to wear with your jeans, khakis or other casual pants, it’s probably a good idea to have a casual pair that’s separate from your athletic shoes.  

What’s great about casual sneaks is that they’re so versatile. 

While most of the various types of shoes on this list have a specific time or place where they look great, a good casual pair of sneakers can be worn in pretty much every other scenario. 

They make perfect walking shoes, which makes them great for running errands, commuting to and from the office or just about any other daily task.

Sharp Selections: 

Dress Sneakers 

man wearing dress sneakers
[image: Wolf & Shepherd / Instagram]

One of the newer styles of men’s shoes to emerge in recent years, dress sneakers essentially take the idea of casual sneakers and dial up the dapperness. 

These are definitely sneakers, but they’ve got the svelte toe shape of dress shoes, which gives them a more sophisticated and refined look. 

They can be worn in all the same scenarios as casual sneakers, but you can also get away with them in dressier/more formal environments, like offices and social situations that require you to be well dressed.  

Sharp Selections: 

Crossovers / Hybrids

Man wearing chinos and hybrids

And speaking of a newer kind of shoes … 

Crossovers, also known as hybrids, go even further toward dress shoes by essentially taking the top half of an actual dress shoe – i.e. a full-grain leather upper with a sophisticated toe shape – and dropping it onto the footbed of a running shoe. 

The result is a shoe with (most of) the sharp style of a dress shoe, and (all of) the comfort and support of a sneaker.  

In addition to a perfect blend of comfort and style, what’s cool about crossovers is that you can get them in a number of different varieties, including everything from a penny loafer to a pair of full brogue wing tips. 

Sharp Selections: 

Boat Shoes

Man wearing chinos and boat shoes
[Image: Sperry / Instagram]

As their nautical name implies, boat shoes (also sometimes called dock shoes) owe their origins to the sea

They were originally designed to help sailors keep a solid grip on the deck.  

But just as drivers offer a lot of advantages outside of the car, boat shoes offer plenty of advantages on land, including a classic style that makes them great to pair with shorts in the summer.   

Personally I like to rock a good pair of boat shoes in casual summer situations where most other people wear sandals, like at the beach or the pool. 

They’re just as easy to slide on and off, but look a lot more stylish, making them easier to transition to non-aquatic events. 

Sharp Selections:

The Most Essential Types of Boots for Men ↓

We’ve put together a (ridiculously comprehensive) list of the 23 most essential men’s boot styles that every guy should own, which I recommend you check out if you want more detail on which boots to where when.

But here are four of my personal favorite styles, which are probably the best, most versatile styles to have in your wardrobe.

Chelsea Boots 

man wearing jeans and chelsea boots

A good chelsea boot offers more convenience than most other types of men’s boots, without sacrificing anything in the style department. 

Where most ankle boots need to be tied with traditional laces, chelseas have an elastic side panel that allows you to slide them on easily. 

The result is a boot that’s not only convenient and simple to slide on, but also more protective from the elements, making chelseas the right shoe for really rainy days when you don’t want your socks to get soaked. 

Sharp Selections: 

Chukka Boots / Desert Boots 

man wearing jeans and chukka boots
[Image: Thursday Boot Co.]

There’s arguably no more versatile piece of footwear than a good chukka boot (also called a desert boot). 

Styled after the boots worn by the British military during their desert campaigns in WWII, chukkas are ankle-high boots that require minimal lacing. 

Chukkas come in a variety of shapes, styles and colors, and nowadays you can even find some models sophisticated enough to wear with a suit

But they’re traditionally thought of as a more casual boot, which is part of what makes them so versatile. 

A good pair of dark brown chukkas can be worn in pretty much any situation where you’d wear blue jeans (which is to say, damn near anywhere). 

Sharp Selections: 

Want to check out more chukkas? We’ve put together a full list of the best men’s desert boots on the market. 

Dress Boots

brown dress boots and plaid pants
What distinguishes dress boots from other styles is the sleek toe shape, which is as sharp and distinguished as dress shoes

“Dress boots” is, admittedly, a more loosely defined category of boot that can encompass a number of other styles: 

You could have chukka dress boots (like the kind referenced above), brogue or wingtip dress boots, cap toe dress boots, or any number of other variations.   

But the important thing to remember is that dress boots all have a sleek toe shape that’s reminiscent of the most sophisticated-looking dress shoes. 

Dress boots can be worn with a suit to help protect your feet from the weather without sacrificing any style.

Sharp Selections: 

Combat Boots

man wearing combat boots facing woman wearing sandals
(That was obvious, wasn’t it?)

Another style of boot modeled after the footwear that soldiers used to wear into battle, combat boots are basically the opposite of dress boots. 

Whereas dress boots could pass for fancy dress shoes from the ankle down, combat boots are usually defined by a rounded toe and thick heel that make them great for trudging through the battlefield, but not really appropriate for the boardroom. 

Fortunately for those of us who aren’t engaged in armed combat, they also happen to work great for pounding the pavement, and can help give your casual looks a more rugged, masculine vibe than just about any other type of footwear.

Sharp Selections: 

More Resources ↓
More Advice on Men’s Boots and Shoes from Irreverent Gent:

Banner Image: Liudmyla Guniavaia / Shutterstock | Illustration: Irreverent Gent

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

4 thoughts on “The 17 Most Stylish Types of Men’s Shoes”

    • 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.

  1. 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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