The best casual shoes for men make dressing for almost any situation a total snap. To be clear, when we say “casual shoes,” we’re using the term liberally (i.e. as a catchall phrase that encompasses everything from suede Chelsea boots to swanky high-top sneakers). Basically, if you wouldn’t wear them to tear up a wedding dance floor or break ankles on the court, you’ll find a version of them included here. Wear ’em day-drinking in the park on a surprisingly mild winter afternoon, wear ’em to your snotty nephew’s backyard piano recital, wear ‘em on that IRL date you lined up months ago in an ill-fated burst of unbridled optimism. But wear ’em you should.
The Best Casual Shoes for Men Shopping Guide
What, you might ask, makes all these shoes so worthy of your hard-earned dollars? An unparalleled ability to elevate your fall cold-weather style, for one. A certain seasonally appropriate versatility, for another. So forget that time-honored debate over whether you should build your outfit from the top down or bottom up—once you throw on a pair of these bad boys, it won’t matter whether you’re rocking denim shorts or sweats. From classic sneakers to chunky loafers and every wild-style permutation in between, consider this your not-so-definitive guide to the very best casual shoes for men on the market right now.
The Cool-Guy Pick
Office dress code varies depending on where you clock in, but chances are you don’t want to wear those precious expensive dress shoes on the daily grind. Instead, the Paraboot “Michael” is both office-approved and built for the rigors of everyday wear. With buffed leather uppers reinforced by a sturdy rubber sole, they keep things polished while withstanding whatever the commute throws at them. You can say they put the business in business casual.
The Not-So-Casual-Friday Pick
Once the laptop closes (let’s be honest, you never fully turn it off) and you’re halfway out the door to happy hour, the last thing you want to sweat is what pair of shoes to slip on. Made in Italy, Margiela’s military-inspired leather sneaker is made from buttery soft calfskin beefed up with a gummy rubber sole. They’re laidback but still leagues above your destroyed white kicks, making them a perfect pair for your busted chinos or the sparkly new selvedge denim you’ve been itching to take out for a spin.
The Office-to-Night-Out Pick
If you’ve been reading GQ Recommends, you’re no stranger to the Camion boot. Why can’t we get enough of this minimalist grail? The do-everything boot is fitted out of sleek-as-hell leather, features zipper access to allow for easy on/off access, and is designed with a distinct squared-off toe and low heel that adds just the right amount of edge without compromising walkability. It’s minimal without being bland, a staple while making a statement. We could wax on about this fashion unicorn but we know what you really care about—can you reasonably sport these while knocking one back with the boys. The answer is a resounding yes!
The WFH Pick
No casual shoe roundup worth its salt is complete without the Birkenstock Boston clog. While you probably wouldn’t sport these for your mid-year review, you most definitely should keep them on hand, er, foot when it’s time to crank out the work from the comforts of your local café. The supple suede uppers, spacious toe box, and podiatrist-approved cork footbed will keep your feet totally relaxed even when your boss is firing off rapid Slacks past 6pm.
The All-Weather Pick
When the weather is unpredictable, as is usually the case when it comes to fall, you want a shoe that can deliver on style, rain or shine. These classic Docs are well-suited to the task, with water-resistant, leather uppers that wipe clean in seconds to their trademark cushioning AirWair sole. They’re built to last for generations but won’t break the bank, making them a guaranteed hit, even when the day at hand can’t decide if it’s winter or summer.
The Actually Casual Pick
You’ve probably got an assortment of Vans and other canvas classics on deck but when you’re looking for something that’s a step outside of the mainstream without fully running away, the Stepney Workers Club Dellow sneaker is the answer. Sure, they’ve got a cushy, flexible footbed and a classic vulcanized, rubber outsole, just like any good sneaker. But the low-profile silhouette, minimal styling, streamlined paneling, and waxy leather uppers give them that certain somethin’ that sets them apart from the staid plimsoll sneakers we’re used to seeing. Maybe that’s why every other creative you know has a pair of these on regular rotation.
The Classic Pick
Even if you’re not making your way up to the (insert your local swanky establishment here), a well-heeled penny loafer is a solid choice for cleaning up any outfit. G.H. Bass’s Weejun loafers are the real OG penny loafer, the prototype of men’s casual shoes for our grandfathers’ generation, and they’re just as cool today as they were back in peepaw’s day. The handsewn leather uppers, moc toe and leather soles make it a prep staple that has range far beyond the ivy-wrapped campuses. Like a pair of blue jeans, the penny loafer can rock with just about anything and is the rare kind of shoe that really can show up on the ‘Best Dress Shoes’ list and the ‘Best Casual Shoes’ list.
