Most modern men today live, work and play in a much more casual world than that of our fathers and grandfathers, so itโs no surprise that menโs casual shoes have skyrocketed in popularity.
Sure, a sleek pair of dress shoes is still (and always will be) a great way to look sharp and stand out.
But in the casual world we live in today, even style-obsessed bloggers like me have to admit that dress shoes arenโt always the best move.
Me, ensuring I sleep on the couch tonight: “This is literally just a fraction of them.”
Today, the most versatile kicks are the kind of casual shoes that you can wear with chinos to satisfy your office dress code, then rock with a pair of jeans on the weekends at a backyard bbq.
To help you find the best casual menโs shoes to suit your taste, budget and personal style profile, in this post I’ll break down our top picks for everyday wear.
Casual-But-Polished Options
Sneakers
Forever the Kings of Casual Shoes
Long gone are the days when a sneaker could only be worn with a pair of athletic shorts or a breezy pair of joggers.
If the world of casual menโs shoes were a jungle, a sharp sneaker may well be the apex predator.
In addition to providing all day comfort, sneakers have always given off an active, casual-cool vibe.
But today modern menโs style has changed pretty drastically, going from the suited-up days of Don Draper to the super chill dress code of Silicon Valley (where casual Fridays have basically grown to encapsulate the whole week).
As a result, a good athletic shoe has become even more essential, and there are plenty of designer sneakers that are as versatile as they are comfy.
In fact, sneaks have become a category all their own.
With a seemingly endless parade of fresh drops and limited-edition sneakers, keeping up with all the latest trends can make shopping for new sneakers more than a little intimidating.
To help streamline things, here are three classic sneaker types to keep in mind.
Sharp Selections:
Dress Sneakers
If the word โsneakerโ makes you think of New Balance shoes you strap on for your daily run, think again.
A minimalist sneaker thatโs sleek and sophisticated enough to wear with a suit, these are the best sneakers if youโre looking for something thatโs casual and comfy, but also a little more sophisticated.
A dress sneaker is a great option if you want comfortable shoes that will elevate your casual wear, so you donโt have to go all the way to a full dress shoe, like a classic cap-toe or a proper pair of leather monk strap shoes.
Sharp Selections:
Boat Shoes
The Perfect Casual Summer Shoe
By far my favorite types of casual shoes, boat shoes are a classic style that offers all the comfortable, cool vibes of flip flops while still letting you look polished and put together.
With their rubber sole and nautical origins, theyโre a great summertime look that pairs perfectly with a loose-fit white linen shirt and a hot summer day on Marthaโs Vineyard.
(Which Iโve never visited and almost certainly never will, but damn if those Kennedy boys donโt know how to dress.)
Boat shoes and deck shoes work great with a pair of flat-front shorts, and are best worn the way they were intended:
With no socks, lots of sun, and, ideally, a light ocean breeze.
And while a classic pair of brown leather boat shoes are always a great choice, nowadays you can get them in a wide variety of colours and fabrics (though I wouldnโt recommend suede for saltwater use!).
Sharp Selections:
Did you knowโฆ?
Paul Sperry, a Navy veteran from New Haven Connecticut, invented the first slip-resistant deck shoe back in 1935.
Nearly a century later, the Sperry Authentic Original Boat Shoe is still one of the most popular โ and one of the best โ boat shoes on the market.
Driving Shoes
Quite Possibly the Best Menโs Casual Slip On Shoes
You can think of driving shoes as a land-locked version of boat shoes.
Theyโre casual summer shoes that work in a lot of the same situations as deck shoes, and convey a similarly laid back vibe thatโs perfect for warmer months.
But unlike deck shoes, drivers work exceptionally well in suede, which, while still casual, lends them a distinctively upscale vibe.
Sharp Selections:
Knit Shoes
A much more modern entry than boat shoes or driving shoes, knit shoes combine style, comfort and breathability.
They often have the sleek toe shape of dress shoes, giving them a slightly more sophisticated look, and the comfortable footbed of sneakers, making them a great choice if youโve previously had a foot injury, and/or you just want a little extra support.
But the real advantage of knit shoes is the breathability they provide.
Instead of a (handsome, if somewhat suffocating) leather upper, theyโre made from lightweight, perforated fabric that lets your feet breathe, making them a great addition to your spring wardrobe.
Sharp Selections:
Casual Boots For a Rugged-But-Refined Look
Chelsea Boots
Chelsea boots are to boots what loafers are to shoes:
Laceless, streamlined, easy and absolutely essential.
Instead of pesky laces that need to be tied up, Chelseas have an elastic panel in the bootโs ankle that makes them easy to slide right on.
As with all the other boot styles on this list, you can find dressier versions of Chelseas that have a sleek toe shape, making them look more like dress shoes.
But you can also find hardier, more rugged Chelseas with a rounded toe and a thick lug sole, which are versatile enough to rock with just about any casual getup.
Sharp Selections:
Crossover Boots
Crossover boots are a newer entry in the world of menโs boots, and offer a few distinct advantages.
First, because theyโre so new, you donโt see them nearly as often, meaning that a good pair of crossovers is a great way to stand out from the crowd.
Second, they combine the upper of a boot with the comfortable supportive sole of a sneaker, making them an excellent choice if you need to be on your feet all day, or if you have any kind of foot pain or other medical issues.ย
Third, since sneakers are inherently more casual, the combination of traditional boot features with the sneaker sole makes crossover boots a natural choice for casual outfits, occupying a similar place in the world of footwear as athleisure does in the world of menโs clothes.
Sharp Selections:
Chukka / Desert Boots
Chukka boots, also known as desert boots, deserve inclusion on this list because theyโre a casual staple that every man needs in his wardrobe.
(Technically there is a distinction between chukkas and desert boots, but to be honest the differences are so subtle that I donโt think you need to worry about it.)
They may not be great for your winter wardrobe if you live somewhere that gets a lot of snow, but come fall theyโre the perfect boot for everyday wear.
As with any shoes, when it comes to chukkas donโt be afraid to spend a little money:
Your best bet is to opt for a pair made from premium materials, which will both look better and offer better support (not to mention the best fit).
Sharp Selections:
Work Boots
Donโt let the name fool you:
Work boots arenโt just for job sites.
In my opinion, there are essentially two different categories of work boots.
Thereโs the heavy-duty work boot, replete with safety features like steel toes and electrical hazard grading, that are meant for serious work.
But thereโs also what you might call stylish work boots (at least, thatโs what Iโll call them).
Theyโre made from the same high-quality materials and craftsmanship, but donโt have all the safety features that weigh down heavy-duty work boots, making them more appropriate for everyday wear.
A good pair of stylish work boots are perfect for adding a rugged, workman-like element to your look, especially when paired with jeans or chinos in dark, earthy colors.
Sharp Selections:
Combat Boots
Named for the standard leather boots that have been issued to soldiers for decades, combat boots (also called service boots) serve a similar role as work boots in a manโs wardrobe.
Their hard-working and rugged origins lend them an undeniable sense of masculinity that helps make your overall look โ and by extension, you โ seem more battle-tested in the process.
As with work boots, they work best with jeans and khakis, and pair especially well with the earthy tones that tend to make up military uniforms: think greens, brown, black and dark beige/camel.
Sharp Selections:
Brogue / Wingtip Boots
Iโll be the first to admit that for a lot of guys, wingtips are way too โdressyโ to be included on a list of the best casual shoes.
But hear me out.
Wingtips, also known as brogues, owe their origins to British hunting parties, when proper gentlemen used to ditch their wool daytime suits in favor ofโฆ
Well, very similar hunting suits, but warmer and made of even thicker wool.
Similarly, theyโd leave the patent leather shoes at home and don brogues, whichโฆ were also made of leather.
But the brogues were perforated with holes that allowed water to seep out, so their socks wouldnโt get too soggy.
Ever since, brogued footwear has been considered the slightly more casual โ and, I would argue, hella more masculine โ alternative to dress shoes.
Thatโs why they work so well with rugged fabrics like denim, and why wing tipped boots were so high on my list of the best boots to wear with a pair of jeans.
Sharp Selections:
Handsome Hack:
If you want to keep the look as casual as it can be, opt for wingtip shoes or boots with a heavy, chunky sole.
Whether brogues or not, sleeker shoes are considered more formal.
Cap Toe Boots
I have a whole post about cap toe oxford shoes, but I didnโt include them in the shoe section above because theyโre a little more โdressed upโ than casual.
Cap toe boots, on the other hand, are a different story.
Cap toe boots arenโt really a distinct type of boot, theyโre more like a type of boot style.
Most of the other types of boots on this list could be found with cap toes, but theyโre worth calling out separately because of what they add to your look.
Opting for a cap toe can help make an otherwise casual getup look smart casual, which elevates the look and helps you look a little more polished and put together, without looking too dressy.
Sharp Selections:
Casual Dress Shoes That Hit the Sharp-But-Not-Stuffy Sweet Spot
(yes, there’s such a thing as casual dress shoes)
Penny Loafers
As easy to wear as they are to slip on, this classic-style loafer is one of the few holdovers from the stylish era of Steve McQueen and Frank Sinatra.
(And still look just as sharp today as they did back then.)
Loafers come in various styles, but my preferred version is the penny loafer:
Falling squarely in between โdressed upโ and โdressed down,โ a leather loafer is the perfect shoe to show that youโre not stuffy, but youโre no style slouch, either.
Handsome Hack:
Want your loafers to look even more casual? Opt for suede instead of leather.
Sharp Selections:
Suede Oxfords
And speaking of suede, one of the best ways to keep your look casual is to wear whatโs arguably the most classic menโs shoe style of all time in one of its most casual fabrics.
While leather oxford shoes tend to be synonymous with โdress shoe,โ opting for suede oxfords simultaneously casualizes the look, while making it more modern.
As a result, suede oxfords are a great every day shoe for business-casual offices where you still want to look well dressed, without crossing the line into looking too โdressy.โ
Plus, theyโre versatile enough to wear with almost everything else in your wardrobe:
They work just as well with a cuffed pair of chambray trousers as they do with a good pair of jeans.
Sharp Selections:
Crossover / Hybrid Dress Shoes
One of the newest types of shoes on this list, crossovers are perfect for guys who want the sharp look of dress shoes and the comfort of sneakers.
Also known as hybrids, these shoes are equal parts stylish and supportive, making them perfect for everything from a business casual office to a well dressed first date.
They combine a lot of the hallmarks of classic dress shoes โ think a svelte toe shape and high-quality leather โ with the cushioned sole of a sneaker.
The result is a shoe thatโs simultaneously dressy and casual, making them perfect for stepping up the style of an otherwise casual outfit, or casualizing a more formal look.
Sharp Selections:
Brogue / Wingtip Shoes
The boot versions were included above, but it bears mentioning that wingtip shoes can also be considered casual, for all the reasons outlined in the boot section earlier.
Nowadays pretty much any leather shoe with a svelte toe shape is considered a โdressโ shoe, but in my opinion any shoe that used to be worn by hunters on a long walk can still count as casual!
To further casualize the look of brogues, opt for a chunky lug sole.
Traditional leather soles give shoes a more refined and sophisticated look, but lug soles are more rugged, which is in keeping with wingtipsโ outdoorsy origins.
