The Only Six Pairs Of Shoes You’ll Ever Need

by   |  in Smart Casual

The truth is, no man needs 20 pairs of shoes.

Hell, most men could get away with much less..

And if you’re interested in creating a lean wardrobe, stocked with versatile, interchangeable pieces, you should strive for fewer choices, not more.

In fact, you only need six pairs of shoes, but a very specific set of six.

Check out the list, then leave a comment telling us which shoes you’re missing, what shoes you own that aren’t totally necessary, and what others (if any) you would add to this collection.

Need the shoes now and no time to read? Here are my recs:

Note: These shoes are listed in order from most casual to most dressy, with a more pricey and a more affordable option. Athletic or activity-specific shoes are excluded… When it comes to finding the best tap dancing / climbing / boxing shoes, you’re on your own.

White Canvas Sneakers

The perfect casual shoes, these can be worn with or without socks and are great for casual, warm weather situations. Think weekend errands, poolside days, beach trips, barbecues and good old fashioned chilling.

Oh, and these make a great substitute for your brown leather flip flops.

canvas shoes

Light Brown Boat Shoes

A step up from white canvas shoes but still casual, boat shoes should usually be worn without socks. You can wear them with shorts, chinos or casual jeans. You can’t go wrong with tan or brown, but feel free to get creative with colors and styles.

boat shoes

Medium Brown Ankle Boots

The desert boot (or chukka) might just be the most versatile men’s shoe on earth. You can wear a brown ankle boot with jeans, chinos, cords or trousers. You can dress them up, down and everything in between.

My Cole Haan Glens are probably my favorite pair of shoes, but you can’t go wrong with the trendy-yet-timeless Clarks Desert Boot (especially in Beeswax).


Rich Brown Loafers

Boat shoes are great, but you really shouldn’t wear them with trousers or in business casual environments. Loafers, on the other hand, are perfect for those situations. They’re easy to slip on and off, which is nice when you’re running late (or trying to get through airport security). They’re dressy enough for almost any professional setting, but they’re still one click below Oxfords

Don’t just reserve loafers for work, though. You can upgrade your warm weather casual looks by swapping out those boat shoes or sneakers for a pair of leather loafers. Bonus points if you ditch the socks. Just make sure to do it right.


Brown Wingtips

These are your work horses. Your go-to dress shoe. Your wingman (well, wingtips, at least). You get the point. If you work in an office, you probably wear some combination of jacket/button up shirt/trousers every day. Brown wingtips will almost always work with these outfits.

Go for something on the darker side, as opposed to a walnut or cognac color. Don’t be afraid to wear a shoe with some decoration.

If you’re going to splurge on any of your six essential shoes, you splurge on these. It will be worth it in the long run to buy resoleable shoes. That said, there are plenty of affordable options.

wing tips

Black Cap Toe Oxfords

If brown wingtips are the practical, fuel-efficient sedan you drive to work everyday, black Oxfords are your motorcycle that only leaves the garage on weekends. Because black shoes are less versatile (and often more boring) than brown ones, you simply won’t wear them as much.

But when you do, it very well may be a special occasion, and you want to look good. So buy nice shoes that will look great for the long haul, and make sure to keep them polished.

You can choose a plain toe or cap toe, but stay away from the broguing, or decoration. After all, these are the shoes you will wear to black tie events, funerals, etc.

black cap toes

Do you have all of these shoes?

Keep in mind that these colors are just guidelines. If you prefer dark brown or blue boat shoes and tan suede desert boots, knock yourself out! Just make sure to diversify your browns so you don’t end up with three different styles of shoe in the same exact shade.

If you buy smart and focus on what shoes you actually need, rather than what’s on sale and what could go with some of your outfits, you can get away only owning these six pairs of shoes.

Once you have this basic arsenal of footwear, you are free to expand and buy some work boots, monk straps, etc. But you won’t have to if you don’t want to. That’s the beauty of a lean, versatile wardrobe.

Would you add anything to the list?