The (Absolute) Best Men’s Casual Shoes

Dave Bowden

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Suitsupply Suede OxfordsMost modern gentlemen 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.

And while a sleek pair of dress shoes is still (and probably always will be) a great way to look sharp and stand out, 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 casual men’s shoes that you can wear at your office, out for drinks with your friends, or on a first date with someone who you hope to make more than a friend.

In this post I’ve laid out the seven best men’s shoes for casual situations and provided a few specific (and, in my humble opinion, stylish-as-hell) examples of each.

The 7 Best Men’s Casual Shoe Styles

And Some Specific Picks That You Should Pick Up

Boat/Deck Shoes

The Epitome of Casual Summer Shoes

Sperry Authentic Originals

By far my favorite type of shoe for summer, boat shoes convey a laidback, casual cool that immediately evokes summers on Martha 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:

M.Gemi | The Barca

(Also available in black)

Sperry Boat Shoes

Learn More ➤


Sperry | A/O Boat Shoe

(Available in multiple colors)

Sperry | A/O Boat Shoe

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206 Collective | Boyer Boat Shoe

(Available in multiple colors)

206 Collective | Boyer Boat Shoe

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London Fog | Harrow Boat Shoe

London Fog | Harrow Boat Shoe

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Sperry | Top Sider

(Available in multiple colors)

Sperry | Top Sider

Learn More ➤


Driving Shoes

Quite Possibly the Best Men’s Casual Slip On Shoes

Blue Driving Shoes

I think of driving shoes as a land-locked version of boat shoes.

They work in a lot of the same situations, and like boat shoes coney a laidback vibe that seems most at home in the summer.

One thing that separates drivers from boat shoes? They 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)

Johnston & Murphy Cort Driving Shoes

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Beckett Simonon | Beaumont Loafers

Beckett Simonon | Beaumont Loafers

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M.Gemi | The Brolio Drivers

(Also available in multiple colors)

M.Gemi Brolio Drivers

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Cole Haan | The Nantucket

Cole Haan | The Nantucket

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Allen Edmonds | Interstate 90

Allen Edmonds | Interstate 90

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Sneakers

The Current Kings of Casual Shoes

Men's white tennis shoes

If the world of men’s casual shoes were a jungle, sneakers may well be the apex predator.

Sneakers have always had a casual-cool vibe, but now that menswear has skewed so far from the suited-up days of Don Draper to the super chill dress code of Silicon Valley, sneakers have become even more essential.

Whether you’re on a date, on the job or on your bike, the right pair of sneakers can help you look sharp and stand out in almost any situation.

The Picks:

adidas Originals Mens Stan Smith Leather Sneakers

adidas Originals Mens Stan Smith Leather Sneakers

Learn More ➤


Beckett Simonon Morgen Trainers

Beckett Simonon Morgen Trainers

Learn More ➤


M.Gemi Lucente Sneakers

M.Gemi Lucente sneakers

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Banana Republic Nicklas Sneakers

Banana Republic Nicklas Sneakers

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Nike Killshot 2 Sneakers

Nike Killshot 2 Sneakers

Learn More ➤


Penny Loafers

Maybe the Best Men’s Casual Leather Shoes

Man wearing tan loafers

As easy to wear as they are to slip on, loafers are one of the few holdovers from the Don Draper/Steve McQueen era that still look just as sharp today as they did a few decades ago.

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

Beckett Simonon | Roy Loafer in Suede

$199 ➤


M.Gemi | The Filare

M.Gemi | The Filare

$278 ➤


Bonobos | The Oxley

Bonobos | The Oxley

$198 ➤


M.Gemi | The Sacca

M.Gemi | The Sacca

$248 ➤


Banana Republic | Dellbrook Italian Leather Loafers

Banana Republic | Dellbrook Italian Leather Loafers

$198 ➤


Suede Oxfords

Look for a Business Casual Shoe? Look No Further

Brown suede oxford shoes

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.

Suede oxfords are perfect for business-casual offices where you still want to look well dressed, without crossing the line into looking too “dressy.”

The Picks:

Bonobos | The Dalton

Bonobos | The Dalton

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Beckett Simonon | The Dean

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Johnston & Murphy | Ridgeland

Johnston & Murphy | Ridgeland

Learn More ➤


206 Collective | Suede Oxfords

206 Collective | Suede Oxfords

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Sperry | The Annapolis

Sperry | The Annapolis

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Chukka Boots

Not a Shoe, But a Staple

Brown chukkas on brick street

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.)

The Picks:

Johnston & Murphy | Copeland

Johnston & Murphy | Copeland

Learn More ➤


Hudson Shoes | Osborne Chukka Boot

Hudson Shoes | Osborne Chukka Boot

Learn More ➤


Suitsupply | Italian Suede Desert Boot

Suitsupply | Italian Suede Desert Boot

Learn More ➤


Nisolo | Chavito Chukka Boot

Nisolo | Chavito Chukka Boot

Learn More ➤


Wingtips/Brogues

Arguably the Best Men’s Casual Shoes to Wear with Jeans

Brown wingtips and blue 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 leather (again, these guys didn’t stray far from their personal style profiles), but 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 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:

Allen Edmonds | Neumok Suede Wingtip

Allen Edmonds | Neumok Suede Wingtip

Learn More ➤


SuitSupply | Cognac Oxford Brogue

SuitSupply | Cognac Oxford Brogue

Learn More ➤


Johnston & Murphy | Reece Wingtip

Johnston & Murphy | Reece Wingtip

Learn More ➤


Beckett Simonon | Kent Wingtip

Beckett Simonon | Kent Wingtip

Learn More ➤


Bonobos | Percy Wingtip

Bonobos | Percy Wingtip

Learn More ➤


What’s Next?

Knowing which kicks constitute the best men’s casual shoes will help you step up your style game in informal settings, which as I mentioned at the top is really most settings nowadays.

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.

The (handsome) devil is in the details

Don’t Let the Other Guys Out-Dress You

Find out how to look sharp and stand out.

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More Resources ↓
More Men’s Shoe Advice and Tips from Irreverent Gent:
More Lists of the Best Men’s Casual Shoes from Around the Web:

Banner image via Sperry

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