If we may be allowed a generalization, men are not shoe people. Most men we know of have a few pairs of shoes in their closets, maybe four or five, and these poor things get worn to death in the service of an unmerciful master.

We’re not saying that having an entire room of your home dedicated to shoes is necessary. We’re not asking you to become Imelda Marcos reincarnate.

What we are saying is that the following ten shoe styles are ones that every man should own, no matter what his age, creed, or station in life.

This guide is the first of many forthcoming shoe purchasing guides that will be targeted to specific personalities. Stay tuned for more in the future, but without further ado:

The Top Ten Shoes Every Guy Should Own

In no particular order, these are the ten shoe styles that any man would benefit from having in his closet.


The black oxford in particular is a crucial dress shoe for any man. Wearable with a suit and even a tuxedo when polished to an exceptionally high shine, a black oxford means business and implies that the wearer knows when to be loud and, just as importantly, when not to be.

Whether a wholecut or cap-toe version, it’s a can’t miss shoe when you need to dress formally.


A brown brogue is incredibly versatile. There are many different brogue styles to choose from, all with varying levels of formality. A smart brown quarter brogue pairs wonderfully with a suit, whereas a chunky full brogue is an excellent choice for denim. Either way, your shoe closet isn’t full without a pair.


A derby shoe (also known as a “blucher“) is kind of the ultimate in dress casual shoes. Their silhouette generally reads “dress shoe” but their open-throat lacing system makes them a bit less sleek, making them a great casual or business casual option. Try a pair in suede for some variation.

Chelsea Boot

A pull-on ankle boot is clutch when the weather cools off. It’s sleek, it’s handsome, and it pairs just as well with jeans as it does with a suit. Try a chelsea boot in pebbled leather for some added texture and visual interest.

Desert Boot

Desert boots are an iconic piece of menswear. Essentially a suede chukka boot with a crepe sole, they are incredibly comfortable and do a lot to elevate a casual outfit in a way that sneakers simply can’t. As an added bonus, even the Clarks’ original versions are still relatively inexpensive so adding a pair to your wardrobe doesn’t hurt too much.


In fairness and accuracy, we should have named this article “The Top Eleven Shoes Any Man Should Own,” because you need two pairs of sneakers: one for wearing out, and one for working out.

Sneakers you can work out in are instantly recognizable. They’re clunky, come in bright colors, and are ergonomically designed to aid you in whatever activity you’re doing: running, playing basketball, doing keg stands, that sort of thing.

Sneakers you can wear out, on the other hand, are sleek and slim and are often made in higher-end materials like leather and suede. These are the ones you throw on with jeans and a t-shirt when you’re hung over at brunch.

Driving Shoe

Driving shoes are like slippers you can wear outside. Super comfortable and sleek, they’re a fantastic alternative to sneakers when you want to dress casually but still have an elevated presentation to your ensemble.

As an added bonus, the rubber nubs that comprise the sole of the shoe actually help to grip brake and gas pedals, making driving shoes ideal for, well, driving.

The downside to driving shoes is their relatively short lifespan for city dwellers who tend to walk a lot more than other folks. The underside of the toe box is exposed and scratches the concrete with every step you take. Wearing these as walking shoes will significantly decrease the amount of time they’re wearable, so be cognizant of that.

Penny Loafer

As far as casual classics are concerned, the penny loafer takes the cake in the footwear world.  Popularized with sack suits in the 1950’s by Ivy League students, penny loafers are always stylish. Available in dressy versions with smooth calfskin uppers and leather soles or casual iterations in suede with driving soles, any guy could use a pair (or two, or three) in his shoe collection.


Shoes with buckles, be they one or two, occupy an interesting place in the footwear canon. Not as dressy as a balmoral but dressier than a derby, monkstrap shoes are the one “fashion” shoe that’s widely accepted but still not commonly worn. There are multiple versions: single and double buckles

Monks look equally excellent with jeans as they do with suits.

Duck Boots

L.L. Bean is the originator of the duck boot, so it’s no surprise that they’re often referred to as a “Bean boot.” L.L. Bean isn’t the only brand that makes these waterproof boots though, and you would be well-served by owning a pair if you live in a place where it ever rains or snows.

Available from various companies in regular or insulated versions (the latter of which is for wear in cold, snowy weather), duck boots are an absolute must in a man’s closet.

Why Have A Well-Stocked Shoe Closet?

Beyond the obvious “Well, shoes are awesome” line of reasoning, it actually makes sense to have more shoes instead of less. Why? Cost and time savings.

To be fair, there is a not-insignificant up-front cost when buying shoes, especially if you opt for decent quality ones. Unless money is no object to you (and more power to you if it isn’t), then you’ll want to be strategic about shopping during promotional periods and leveraging other discounts. We’re fans of Allen Edmonds’ Factory Seconds and have had rather good luck with our finds there.

Perhaps counterintuitively, spending more money on the quantity of your shoes will increase their lifespan.You wear each pair less, meaning that less wear and tear occurs over time. In the long term, you save you money as a result.

Furthermore, buying repairable shoes means that you don’t have to pay full freight for new shoes every couple of years, but rather get them resoled or otherwise repaired for a cost that’s significantly less than new shoes. This means less time wasted looking through new shoes that you may or may not even buy.

Conclusion: General Shoe Guides

In case you missed it, we have a full shoe style guide that will get you up to speed on all the main footwear styles you can own. We encourage you to take a look and start panning the shoes you’d like to have in your closet!