There’s an obvious reason why modern guys would want to find the best casual shoes for men:
Most of us live, work and play in a much more casual world than that of our grandfathers, and we need shoes that reflect our reality.
I say this as someone who loves the classic style of Don Draper and Steve McQueen.
For that generation, weekdays meant a crisp suit and patent leather dress shoes, while weekends were for sharp sweaters and a tasteful pair of loafers.
Don’t get me wrong: a sleek pair of dress shoes is still (and probably always will be) a great way to look sharp and stand out.
But in the casual world we now live in, even I have to admit that it’s not always the right move.
Today, the most versatile kicks are the the casual mean’s shoes that you can wear all day at the office, then out for drinks with your friends.
(Or on a first date with someone who you hope to make more than a friend.)
To help you step up your style in this post I’ll break down the seven most important types of casual shoes guys need to know about, and share my picks for the 35 best men’s casual shoes on the market.
Step Up Your Shoe Game
The 7 Best Types of Casual Shoes for Men
Boat/Deck Shoes
The Perfect Casual Summer Shoe
By far my favorite types of casual shoes, boat shoes are perfect for casual wear because they give off a laidback, comfortable cool.
With their rubber sole and nautical origins, they’re a great summertime look that pairs perfectly with a loose-fit white linen shirt and a hot summer day on Martha’s Vineyard.
(Which I‘ve never visited and almost certainly never will, but damn if those Kennedy boys don’t know how to dress.)
Boat shoes and deck shoes work great with shorts, and are best worn the way they were intended:
With no socks, lots of sun, and, ideally, a light ocean breeze.
The Picks:
Sperry Authentic Original Boat Shoe
(Available in multiple colors)
206 Collective | Boyer Boat Shoe
(Available in multiple colors)
London Fog | Harrow Boat Shoe
Sperry | Top Sider
(Available in multiple colors)
Driving Shoes
Quite Possibly the Best Men’s Casual Slip On Shoes
I think of driving shoes as a land-locked version of boat shoes.
They’re casual summer shoes that work in a lot of the same situations as deck shoes, and convey a similarly laidback vibe that’s perfect for warmer months.
But unlike deck shoes, drivers work exceptionally well in suede, which, while still casual, lends them a distinctively upscale vibe.
The Picks:
Johnston & Murphy | The Cort Drivers
(Also available in black)
Beckett Simonon | Beaumont Loafers
M.Gemi | The Brolio Drivers
(Also available in multiple colors)
Cole Haan | The Nantucket
Taos Convertawool
(Available in multiple colors)
Note:
These are not true drivers (obviously), but are similar in that their comfortable slip-ons with a rubber outsole.
I wouldn’t necessarily recommend wearing these out and about, but they’re the perfect house shoe for guys who want to keep their feet warm (and stay stylish) at home.
Sneakers
The Current 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 men’s shoes were a jungle, a good minimalist sneaker may well be the apex predator.
Easily the most comfortable shoes, sneakers have always had a casual-cool vibe.
But today modern men’s 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.
Whether you’re on a date, on the job or at a backyard bbq, the right pair of dress sneakers is a great option that can help you look sharp and stand out in almost any situation.
The Picks:
adidas Originals Mens Stan Smith Leather Sneakers
Beckett Simonon Morgen Trainers
M.Gemi Lucente Sneakers
Banana Republic Nicklas Sneakers
Nike Killshot 2 Sneakers
Penny Loafers
Maybe the Best Men’s Casual Leather Shoes
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 “dressed up” and “dressed down,” a leather loafer is the perfect shoe to show that you’re not stuffy, but you’re no style slouch, either.
| Handsome Hack:
- Want your loafers to look even more cas? Opt for suede instead of leather.
The Picks:
Beckett Simonon | Roy Loafer in Suede
M.Gemi | The Filare
Bonobos | The Oxley
M.Gemi | The Sacca
Banana Republic | Dellbrook Italian Leather Loafers
Suede Oxfords
Look for a Business Casual Shoe? Look No Further
And speaking of suede, one of the best ways to keep your look casual is to wear what’s arguably the most classic men’s shoe style of all time in one of its most casual fabrics.
While leather oxfords tend to be synonymous with “dress shoe,” 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 “dressy.”
Plus, they’re 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.
The Picks:
Bonobos | The Dalton
Beckett Simonon | The Dean Classic Cap-Toe
Johnston & Murphy | Ridgeland
206 Collective | Suede Oxfords
Sperry | The Annapolis
Chukka Boots
Not a Shoe, But a Staple
OK fine, technically these aren’t shoes per se, they’re boots.
But they deserve inclusion on this list because chukka boots, also known as desert boots, are 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 don’t 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 they’re the perfect boot for everyday wear.
As with any shoes, when it comes to chukkas don’t 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).
The Picks:
Johnston & Murphy | Copeland
Hudson Shoes | Osborne Chukka Boot
Suitsupply | Italian Suede Desert Boot
Nisolo | Chavito Chukka Boot
Wingtips/Brogues
Arguably the Best Men’s Casual Shoes to Wear with Jeans
I’ll be the first to admit that for a lot of guys, wingtips are way too “dressy” 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 of…
Well, very similar hunting suits, but warmer and made of even thicker wool.
Similarly, they’d leave the patent leather shoes at home and don brogues, which… were also made of leather.
But the brogues were perforated with holes that allowed water to seep out, so their socks wouldn’t get too soggy.
Ever since, brogued shoes have been considered the slightly more casual — and, I would argue, hella more masculine — alternative to dress shoes.
That’s why they work so well with rugged fabrics like denim, and why wingtipped boots were so high on my list of the best boots to wear with a pair of jeans.
| 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.
The Picks:
SuitSupply | Cognac Oxford Brogue
Johnston & Murphy | Reece Wingtip
Beckett Simonon | Kent Wingtip
Bonobos | Percy Wingtip
You Know the Best Men’s Casual Shoes
Now Learn How to Step Up the Rest of Your Style
Knowing our top picks for the best men’s casual shoes can help you go from an average style guy to a sharp dressed man.
And while shoes are definitely a key piece of the puzzle that is sharp style, menswear is kind of like those gigantic jigsaw puzzles my grandpa loves to do:
It has a thousand pieces and takes a helluva longtime to figure out.
Fortunately, I’ve put together a checklist that will help you shorten your learning curve.
I’ve laid out the most crucial Nine Details You Need to Nail in order to look sharp and out-dress the other guys.
Use the form below to sign up and I’ll send the checklist straight to your inbox so you can start stepping up your style.
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More Resources ↓
More Men’s Shoe Advice and Tips from Irreverent Gent:
- 9 Must-Have Men’s Boot Styles
- The (Absolute) Best Shoes for No Socks
- The 25 Best Men’s Summer Shoes
- The Best Red Wing Boots for Men to Wear Daily
- The Best Shoes for Men to Wear with Joggers
- The (Absolute) Best Cap Toe Oxford Dress Shoes for Men
- The Most Stylish, Comfortable & Best Shoes for Male Teachers
- The 8 Most Stylish Types of Shoes for Men
- The Best Men’s White Sole Dress Shoes
- The Most Stylish Shoes to Wear with Chinos
- The Absolute Best Shoes (& Shoe Colors) to Wear with Khakis
- The Most Comfortable Golf Shoes for Walking the Course
- The Most Stylish Shoes for Men to Wear with Jeans
- 17 of the Best Chukka Boots for Men
- The 21 Best Shoes to Wear with Shorts
- The (Absolute) Best Monk Strap Shoes for Men
- The Best Casual Loafers for Men
- The Best Red Bottom Dress Shoes for Men
- The 9 Most Stylish & Comfortable Dress Shoes That Feel Like Sneakers
- The 9 Most Stylish Casual Boots to Wear with Jeans
- In-Depth Wolf and Shepherd Shoes Review
- The Best Italian Shoe Brands for Men
More Lists of the Best Men’s Casual Shoes from Around the Web:
Banner image via Sperry
