If you want to make your life easier, you should strive to have fewer choices, not more. And when it comes to the essential mens shoes, there are only a handful that qualify as “must-haves”.
The truth is, no man needs 20 pairs of shoes. Hell, most men could get away with much less.
So which ones are the essentials for a smart casual wardrobe, you may be asking. I’ll be going over that in this article, and lucky for you, I’ve narrowed it down to six distinct types of shoes that will cover you in practically all social situations.
It’s a very specific set of six men’s shoes, so check out the list and compare that with what you have. Is it time to get rid of a few pairs, or stock up on a couple new ones to round out the collection?
Need the shoes now?
If you don’t have time to read the details, or want to save it for later, here are my recommendations so you can easily shop for what you need. I included a mix of affordable and investment-worthy options.
Whether you’re walking, working, or simply kicking it, the versatile and understated Royale Blanco is going to get you where you need to go.
Old school never looked so fly. Rep your era to the fullest in a pair of these classic Chucks from Converse.
"Our finest blucher mocs are crafted in time-honored fashion from the very best leather. So strong, durable and timeless, you'll wear them for years (even decades) to come." –L.L.Bean
Whether you’re sporting your favorite pair of jeans or a sport coat and chinos, the Laval Chukkas have you covered. These are one of the few styles that ensure you’ll never be overdressed or underdressed.
"When you want to go classic, but not as formal as an Oxford, the Roy Loafer is the shoe for you.... The Roys play it cool with cuffed jeans and shorts. They also get down to business when paired with a suit or dress pants." –Beckett Simonon
Make a memorable impression with the refined elegance of the cap toe Allen Edmonds Strand lace-up oxford
A classic Balmoral style lace-up cap toe dress shoe.
Made to order. "...the timelessness of the Dean Oxfords will shine through no matter what you pair them with." –Beckett Simonon
When it comes to leather: Are brown shoes or black shoes better?
Most of the essential shoe styles we mention here are leather. You may be wondering: Should I buy black leather or brown leather?
In most cases, we suggest some shade of brown leather. A medium to dark brown leather color is perfect for a smart, sharp, business casual wardrobe. A bonus? They easily match with plenty of different colors you may have in your outfit.
A black leather shoe tends to come off as too dressy and formal. Unless you’re wearing a suit and tie every day, you’d be better off choosing brown leather or suede as your default pick.
The Six Essential Mens Shoes (For A Smart Casual Wardrobe)
FYI: These footwear options are listed in order of formality from most casual to most dressy. As mentioned above, I’ve tried to include a mix of affordable and investment-worthy options.
Also, since we’re focused on helping you build a versatile smart casual wardrobe, we’re omitting any athletic shoes, activity-specific shoes, or fashion-forward / trendy shoes. When it comes to finding the best Balenciaga chunky sneaker / tap dancing shoe / climbing shoe / Nike running shoe, you’re on your own.
The White Sneaker (Leather or Canvas)
White sneakers are the perfect casual shoes. The slightly more elevated leather sneaker can be used in both casual and smart casual outfits. Typically these fall into the “minimalist sneaker” category.
The sneakers made from canvas can be worn with or without socks and are great with a casual outfit, especially in warm weather situations. Think weekend errands, poolside days, beach trips, barbecues and good old-fashioned chillin.
White is a solid option and one I always recommend—I throw these in the wash when they’re dirty—but a pair in off-white, grey, navy, or black can be just as versatile.
Another great option for a casual shoe, especially if you’re near a body of water? The espadrille.
Espadrilles are cotton canvas slip-on style shoes with a rope-soled bottom. I like to wear these near the beach or by the pool as a flip flop or sandal alternative. Consider espadrille shoes if you already have a white canvas sneaker in your arsenal.
Whether you’re walking, working, or simply kicking it, the versatile and understated Royale Blanco is going to get you where you need to go.
Old school never looked so fly. Rep your era to the fullest in a pair of these classic Chucks from Converse.
The Boat Shoe (Or Blucher Moc)
A boat shoe (or my preferred style, the blucher moccasin) is a step up from white canvas shoes but still very much casual. Boat shoes are meant to be worn without socks, but if you can’t do the no sock thing, at least go for invisible no-show socks or sock inserts.
As far as what pants to wear, pretty much anything casual works, from shorts, to chinos or casual jeans. And when it comes to leather color, you can’t go wrong with tan or brown, but feel free to get creative with colors and styles.
Already have a boat shoe, or want something a bit different, yet still the same level of casual? Try a driving shoe (check out our video for more warm weather shoe styles).
"Our finest blucher mocs are crafted in time-honored fashion from the very best leather. So strong, durable and timeless, you'll wear them for years (even decades) to come." –L.L.Bean
The Brown Leather Chukka Boot
The chukka boot (or desert boot) might just be the most versatile men’s shoe on earth. You can wear a brown leather boot with jeans, chinos, cords, or trousers. You can dress them up for a business casual office, down for drinks with friends, and everything in between.
Feeling a bit more daring? Already have a brown leather chukka boot? A chelsea boot is another great option.
Is a chukka boot a dress boot?
Chukka boots are inherently more casual. Dress boots do exist, however, but they look more like dress shoes, just with a taller shaft.
A handsome, refined pair we like to recommend here on EG are the Laval chukkas from Beckett Simonon. Of course you can’t go wrong with the timeless Clarks Desert Boot (especially in Beeswax). If you’re more of a suede chukka fan, that’s certainly an option with the Clarks as well.
Whether you’re sporting your favorite pair of jeans or a sport coat and chinos, the Laval Chukkas have you covered. These are one of the few styles that ensure you’ll never be overdressed or underdressed.
A Loafer in Rich Brown Leather
Boat shoes and blucher moccasins 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 a more formal Oxford shoe. You can get a great pair of loafers in standard leather or suede.
Because of this, for a smart casual / business casual wardrobe, I’d consider a loafer the essential shoe. Bonus points if you get this specific style of loafer (in my opinion, more sleek than a standard penny loafer).
Don’t reserve loafers just 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 (or wear no-show socks). Just make sure to do it right.
Should you go for a penny loafer? A tassel loafer? A kiltie loafer? (Say what now)
The specific loafers I like are pennies, but they have a more elongated, almond shaped toe. I explain in detail in this article if you’re curious. But I also think a standard penny loafer or a more decorative tassel loafer is great for a smart casual wardrobe.
"When you want to go classic, but not as formal as an Oxford, the Roy Loafer is the shoe for you.... The Roys play it cool with cuffed jeans and shorts. They also get down to business when paired with a suit or dress pants." –Beckett Simonon
Brown Brogues / Wingtips
These are your work horses. Your go-to dress shoe. Your wingman (well, your wingtips, at least). You get the point.
If you work in an office, you probably wear some combination of jacket / button up
What’s the difference between a brogue and a wingtip?
- “Brogue” refers to the general style of shoe with perforations, or holes, in intricate patterns and designs throughout the shoe’s upper.
- “Wingtip” is the brogue design found on the leather shoe’s toe, extending the toe cap in a wing shape to both sides of the shoe.
Fun fact: In terms of formality level, a brogue shoe is considered less formal than a plain leather dress shoe with no broguing. Read all about brown dress shoes in our extensive guide.
Another dressy option, if you already have a wingtip shoe, is a monk strap shoe! More or less on the same formality level, monk strap shoes fasten with a buckle and strap across the vamp. They’re more rakish and a good alternative to a laced dress shoe or loafer.
I wouldn’t consider monk strap shoes an essential, however. So if you still don’t have a standard dark brown wingtip shoe, buy that first.
Going back to the essential brown wingtips, shop for something on the darker side, as opposed to a walnut or cognac color. Brogues may look fancy to you at first, but don’t worry, they’re really easy to pull off. Don’t be afraid to wear a shoe with some decoration.
And yes, you can wear these easily with dark blue jeans as you can with charcoal grey or navy trousers. Or really, anything in between.
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 shoes that can be resoled. Sole protectors wouldn’t hurt, either. That being said, there are plenty of affordable options.
Make a memorable impression with the refined elegance of the cap toe Allen Edmonds Strand lace-up oxford
Black Cap Toe Oxfords
If brown leather wingtips are the practical, fuel-efficient sedan you drive to work everyday, black leather oxfords are your motorcycle that only leaves the garage on weekends.
Because black oxford shoes are less versatile (and often more formal and serious) than any brown leather shoe you may own, you simply won’t wear them as much.
But when you do bust out the black oxfords, 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.
What’s the difference between an oxford shoe and a derby shoe?
You may have heard these two terms when it comes to dress shoes. They simply refer to the open- or closed-lace style, or how the eyelets were stitched onto the vamp.
An oxford (also known as Balmoral) shoe has closed lacing, and is considered a more formal shoe. A derby (also known as a blucher) shoe has open lacing and is considered more casual.
Regarding toe style, you can choose a plain toe or cap toe, but stay away from any broguing for these essential oxfords. Remember that brogue designs on a shoe are less formal, and these black oxfords are the shoes you will wear to black tie events, funerals, etc.
Made to order. "...the timelessness of the Dean Oxfords will shine through no matter what you pair them with." –Beckett Simonon
A classic Balmoral style lace-up cap toe dress shoe.
Do you have all these men’s footwear options?
Keep in mind that these colors are just guidelines. If you prefer blue boat shoes, or tan suede desert boots, knock yourself out! One word of advice: 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?
This article was originally published on April 3, 2014 and written by Brock McGoff from The Modest Man. It has since been edited and updated by the team at Effortless Gent.
