Give Your Feet Some Time Off With These Cool Yet Casual Shoes For Men

The best men’s casual shoes are our number one choice when we’re off-duty and ready to let off steam. When it’s time to chill out, recharge batteries, and enjoy some R&R, casual shoes are what we want on our feet, whether it’s a pair of vacation-ready espadrilles or suave driving shoes. The best casual shoes for men are like the footwear equivalent of an out-of-office email. They signal to everyone that work’s out and playtime has arrived. 

That said, these days the line between office-appropriate attire and casual weekend wear is more blurred. And so, whether your office has a business casual or smart casual dress code, many casual shoes for men can also become your go-to workday picks. 

The best men’s casual shoes offer a refreshing alternative to more formal footwear. When the rest of our shoe collection feels stale and serious, casual shoes, with their mellow and easygoing vibe, are a welcome relief. Not only are these cool shoes for men super comfortable but they also create a don’t-sweat-the-small-stuff attitude compared to more dressy shoes. 

So what are your options when it comes to men’s casual shoes? Well, you’ve got lots. There are cool and sporty sneakers, preppy boat shoes, elegant and refined loafers, glamorous driving shoes, stress-free slip-ons, the favored business casual shoes that are Derbys and brogues, and Chukka or Chelsea boots for those seeking something that will survive cooler seasons. 

To help you decide, we’ve picked out the best casual shoes when it comes to each style, from classic white sneakers to jet-set-approved deck shoes. Some of these men’s casual shoes

could easily be worn to the office, some are pure date-night material, and some are as obligatory as a passport when it comes to packing for your next holiday. 

Men’s casual shoe guide: Must-own shoe styles

To facilitate your navigation, we’ve organized our list of the best casual for men by category:

1. Sneakers
2. Boat shoes
3. Loafers
4. Brogues & Derbies
5. Driving shoe
6. Ankle boots and Chelsea boots
7. Chukka boots
8. Slip-Ons

Check our special men’s casual shoes buying guide after the list to see exactly what you should pay attention to shopping for your next pair of shoes online.

Sneakers

Gone are the days when men’s sneakers were restricted solely to sport and the gym. Today, you can wear a pair of the best casual sneakers for men to the office, on a date, and even to semi-formal occasions. Not only will people not blink an eye. They’ll also give you some serious style kudos. 

The best everyday sneakers offer a mood of sleek yet relaxed 21st-century sophistication—and are also (crucially) incredibly comfortable to spend a day in too.

Axel Arigato Clean 90

We’re obsessing over Axel Arigato’s line of Scandinavian-meets-Japanese minimalist footwear and our favorite pair of men’s casual shoes have to be the brand’s Clean 90s. These Axel Arigato’s top-rated sneakers are the absolute epitome of timeless chic—seen here in versatile black, although also available in other colorways. With their super-smooth leather, set on a cushioned footbed and with a supportive high rubber cup-sole, they’re some of the best everyday shoes for men around. 

Best for: Ultra-charismatic shoes that go with absolutely anything.

Koio Capri Triple White

We’re always on a quest to discover that flawless and ever-dependable white sneaker. And Koio has created it with the Capri Triple White. Some of the best men’s casual shoes we’ve seen, these sneakers are hand-made in Italy from deluxe full-grain leather and combined with a long-lasting and grippy rubber sole. Wear them to the office, art gallery, cocktail bar, swanky restaurant, and even in the park throwing sticks for the dog. Scuff them up or keep them impeccably clean—either way, they’ll secure you style points.

Best for: A classic wardrobe staple finally finds perfection.

Nike Air Force 1 Mid ‘07

We love Nike Air Jordans and we love Nike running shoes. And we also rely on the brand to fulfill our casual footwear needs with the Nike Air Force 1 Mid ‘07. The Swoosh has mastered the art of balancing convenience and aesthetics with some of the most comfortable shoes for men we’ve come across. These sneakers feature a blister-resistant and supportive padded mid-cut collar, a hook-and-loop closure (harking back to old-school basketball styles), and toe perforations to keep your feet cool and calm. Nike at its absolute best. 

Best for: Streetwise chic that will survive hoop-shooting too. 

Adidas Ultraboost

One of the sportier silhouettes in our rundown of the best casual sneakers for men, the Adidas Ultraboost has been converting people to its athletic-meets-urban style since 2015. It was one of the first running shoes to be adopted by fashion’s tastemakers who saw it as a cool accompaniment to streetwise get-ups. The Ultraboost features a sock-like Primeknit upper digitally designed for seamless and lightweight comfort (and minimal waste) and heel-to-toe energy return thanks to its Boost technology. 

Best for: A sneaker that will help you run for the bus and look stylish once you catch it.

Oliver Cabell Low 1

Oliver Cabell makes some of the best sneakers for men—sneakers that are both high-end and affordable. We pretty much live in our Low 1s. This impeccably trendy casual sneaker comes in a range of colorways (although we’re suckers for timeless white) and is made of full-grain calfskin leather with durable and lightweight rubber outsoles. As with all Oliver Cabell sneakers, the Low 1 comes with a full price breakdown so you can see exactly where your money is being spent. 

Check our in-depth review of Oliver Cabell’s sneakers and our profile on Oliver Cabell’s brand.

Best for: Understated allure from a brand that always gets the price right.

Boat shoes

Boat shoes, aka deck shoes, may sound like something you can only wear if you happen to own a superyacht but, these days, it’s totally fine to wear boat shoes to places other than a boat. In fact, they can even pass as casual work shoes in a pinch. 

Team them with cropped jeans or chinos and a polo shirt for a look that will literally never go out of fashion. Want a pair of shoes that offer instant summery style and immediately make you feel like you’re on holiday? Grab yourself a pair of these easy-breezy warm-evening-ready creations. 

Allbirds Tree Skippers

In case you haven’t heard, Allbirds have earned themselves status as the world’s most comfortable shoe. And one of our favorite styles by the brand is the Tree Skipper. These boat shoes feature an S-curved foam that mimics the flex of your feet for all-day comfort, and, like all Allbirds shoes, are made of renewable materials—specifically responsibly sourced eucalyptus tree fiber which is smooth, breathable, and cool. Some of the most comfortable shoes for men around. 

Best for: Unparalleled comfort with an eco-conscience.

Sperry Burnished-Leather Boat Shoes

With boat shoes, it’s best to keep it simple and straightforward with nice and expensive-looking leather—as with these beauties from Sperry, some of the best men’s casual shoes for summer vacations. The label makes high-quality preppy-style staples and these shoes look like the kind of footwear worn by the ocean-traversing big-boat-owning elite of this world. Tanned to a gorgeous burnished hue named ‘amaretto’ to get us in the mood for cocktail hour, these Sperry’s boat shoes are also stain and water-resistant.  

Best for: Feeling like you’re just one paycheck away from pulling up anchor on a private yacht.

Fear of God Suede Boat Shoes

Up the style ante with these cool shoes for men by LA-based brand Fear of God. The label is known for its effortlessly sophisticated designs that combine next-level luxury with a nonchalant cool-kid appeal and these Fear of God’s shoes have a definite deluxe yet unfussy feel to them. You’ve got a round moc toe, tonal lace-up closure, smooth buffered leather lining, and a treaded crepe rubber sole that will ensure you don’t go flying off the boat deck. 

Best for: Like the coolest of summer vacations in footwear form. 

Loafers

If you’re in the market for a new pair of casual shoes for men, it doesn’t get much more easygoing and relaxed than a pair of heel-less, lace-free, slip-on shoes that are basically the outdoor equivalent of a slipper. The best loafers can actually also pass as casual work shoes and are a super stylish alternative to sandals. From clean-lined carefree creations in suede to more decadent offerings in gleaming leather, here’s why loafers are some of the best everyday shoes around. 

Amberjack The Loafer

Looking for a simple way to give your get-up a style boost and add allure for a Friday night date? Just slip your feet into these Amberjack loafers. Made of elegant beige suede, these cool shoes for men are heaven for our feet and look impeccable even when teamed with something as lowkey and basic as jeans and a polo. Hailing from one of our favorite men’s shoe brands, they’re timeless and iconic without even trying.

Check our hands-on Amberjack Loafers review to see how they fit on the feet. You can also read our other Amberjack shoes review and learn about the Amberjack brand here.

Best for: Unflappable and fuss-free fashion for basically any casual event (and summer walk).

M. Gemi The Sacca

M. Gemi is our number one brand when it comes to traditional hand-crafted Italian luxury. We love The Sacca loafers for their comfortable and flexible fit, buttery soft suede upper, and classic silhouette. Team these men’s casual shoes with an elegant cashmere sweater in a neutral shade plus tailored trousers and you’ve got the perfect relaxed yet refined outfit. Also available in a delectable shade of yellow (aptly named limoncello) if you’re feeling daring. 

Best for: Stress-free sophistication with a dash of pared-back prestige.

G.H. Bass & Co. Weejuns Larson Penny Loafers

For a pair of loafers that feel a little more structured and formal, we recommend this elegant pair by G.H. Bass & Co. The American company known for its commitment to crafting high-quality classics imbued with heritage appeal has done it again with these Weejuns Larson Penny loafers. Made of durable leather, they feature an almond toe (not too pointy, not too round), a low block heel, and a leather sole. Some of the best casual shoes for men if you’re all about eye for detail. 

Best for: Adding sharp style to an otherwise easygoing, summer-loving, cocktail-sipping outfit. 

Brogues & Derbies

It’s not easy to walk the line between formal and relaxed successfully but brogues and Derbys can confidently claim the title of some of the best casual shoes for men around. They’re sophisticated enough to show up at the office for important client meetings but not so straight-laced that you couldn’t also wear them at the weekend. They’re the versatile and fashion-fail-proof shoes every man needs.

Cole Haan Oxford

This classic Oxford Brogue by Cole Haan is perfectly proportioned and carefully considered, offering old-school dapperness with modern-day comfort. It’s made of 100% leather and has a rubber sole for durability, anti-slip grip, and flexibility. There’s also an EVA midsole for extra cushioning. The traditional Oxford wingtip offers an air of quiet dignity, making these a must-buy if you’re looking for business casual shoes for men.

Best for: Proof that nothing beats a classic. 

Dr Martens Derby

The best way to add edge and intrigue to a standard pair of Derbys? Choose a pair by Dr Martens. The brand’s signature yellow stitching immediately lends any pair of casual shoes for men grit and energy along with a hint of military-style functionality. These Derbys feature a three-eye lace-up closure, a round toe, and the label’s treaded Air Cushion rubber sole to put bounce in your stride.  

Best for: A gutsy spin on a perennially cool silhouette. 

Grenson Joel Derby

Made by classic British brand Grenson, a company known for its quality and heritage craftsmanship, these Joel Derbys are some of the best everyday shoes for men. Made from grained black leather, they’re a more relaxed alternative to Oxfords. You’ve got the brand’s Extralight commando soles, too, which means all-day comfort—plus enough traction for wet city streets. Team with a knitted sweater and light-colored chinos.

Best for: Super sturdy yet stylish Derbys that are chunky and stompy in all the right ways.

Thom Browne Brogues

Looking for a pair of brogues that can guarantee entry to the most exclusive venues in town? Shoes that wouldn’t look out of place in 5-star establishments while still being relaxed enough for wearing on the school run or to Saturday’s brunch? Try these Thom Browne Brogues—some of the best business casual shoes for men. Available in black leather, they have an elegant round toe, leather insole, pull tab at the back for easy on and off, and punch-hole detailing.

Best for: Cruising from park strolls to cocktails at the hottest drinking holes.

Clarks Malwood

Don’t you get bored of always wearing brown and black? We’re grateful to Clarks for encouraging us to live a little and experiment with these eye-catching Malwood Plain Navy shoes that are formal-wear appropriate without feeling too dressy. A great pair of casual work shoes, we love their unique and contemporary blue hue. The lightweight EVA sole is an added bonus. 

Best for: Playing around with a super chic and imaginative take on the classic casual shoe.

Driving shoe

Great news. You don’t actually have to be the owner of a Bugatti or other sports car to wear driving shoes. While they were originally designed to be lightweight and grippy enough for drivers to get a solid footing on the pedal, today they’re a great option if you’re looking for unique casual shoes for men. Remember to go sockless. A flirty flash of ankle is essential. 

M. Gemi The Banco

Driving shoes can be a little ostentatious. Keep it relaxed with these driving shoes by M. Gemi, available in a range of timeless neutrals including brown and olive green. There’s something of the penny loafer about this driving moccasin, making it perfect for dinners and drinks at upmarket joints around town. Handmade in Toscana in Italy, they’d look particularly good on the terrace of an Italian wine bar. Men’s casual shoes don’t come much more classy than this. 

Best for: Balmy evenings with an Aperol spritz in hand.

Tod’s Gommino

Tod’s Gommino is one of the most iconic driving shoes out there and the very apex of Mediterranean glamour. In other words, a classic. Expect scrupulous attention to detail, a welcome commitment to comfort, and rubber pebbles on the sole for an extra firm grip when you press down on the accelerator. Pair these cool shoes for men with slim-fitting jeans or cotton shorts and a chambray shirt. 

Best for: A traditional driving shoe born to breeze along coastal roads with the car roof down.

Gucci Driver Signature Moccasin

Meticulous craftsmanship, timeless style, and an aura of exclusivity—that’s what we want from our driving shoes and that’s exactly what Gucci delivers with these black signature driving moccasins. Some of the best casual shoes for men by a designer brand, they’re set on a grippy rubber sole (in case you do need to jump in the driving seat of an Italian roadster) and feature the Gucci logo on the toe to indicate your discerning taste.  

Best for: A trend-transcending driving shoe from an indisputable fashion titan. 

Ankle boots and Chelsea boots

When it comes to winter, we need something a little more robust than boat shoes and loafers. But we still want the same easygoing, devil-may-care, keeping-it-casual attitude. Step forward, ankle boots and Chelsea boots. Whether in leather or suede, black, brown or something more audacious, these men’s boots are some of the most comfortable shoes for men. They’ll be your sidekick through cooler temperatures, keep you stable on slippery city streets, and even make you look like you have a side hustle in an indie band. 

New Republic Chelsea Boot

If you’re looking for a pair of fail-safe, always-appropriate, season-after-season shoes, grab yourself a pair of these cool boots from New Republic, some of the best men’s casual shoes for under $150. They’re available in leather and suede and feature all the hallmarks of a classic Chelsea boot, including a pull tab, elastic gusset, and a crepe outsole for flexibility with minimum weight. 

Best for: Free, easy, and fashion-forward functionality.

Axel Arigato Chelsea Boot

It’s impossible to make Chelsea boots look uncool. See Axel Arigato’s take on the classic silhouette. No matter what you wear them with, you’re going to get people’s attention with these boots by Axel Arigato. Made of premium leather, they feature elastic side panels and a subtle but oh-so-suave Arigato stamp in gold. A thread pattern adds grip to the outsole while the pull-on loop makes it easy to get these beauties on and off. Team with a trench coat for maximum impact. 

Best for: Slick urban refinement with a hint of rocker too.

Moncler Boots

Chelsea boots aren’t the be-all and end-all of ankle boots. For something more hard-hitting and combat-ready, try these Moncler Vancouver boots in nubuck. Moncler makes clothes that straddle the worlds of sport and urban living. As a result, these Moncler boots are perfect for striding around town with a biker, field jacket, or bomber jacket but these cool shoes for men could also hold their own in rustic environments too. 

Best for: Down-to-earth and straight-talking boots that still have an eye for design.

Oliver Cabell SB 2

If you like lace-up ankle boots but you want to steer clear of the military aesthetic, then grab yourself a pair of the SB 2 Prairie Roughout Mini Ripples by Oliver Cabell. As the name suggests, there’s an air of pastoral backcountry about these casual shoes for men and we dig it. They’re the kind of shoes we could wear snapping photos of local flora and fauna before heading to the local pub for a dram of fine whiskey. 

Best for: Boots to take you from morning to evening, tedious meetings to after-dark excitement. 

Chukka boots

The quintessential casual boot, the Chukka originated in India where it was favored by polo players. Whether or not you play the sport—or have ever mounted a horse—it doesn’t matter today. Also known as desert boots, these men’s casual shoes have become an everyday essential for stylish modern gentlemen with their ankle-high suede or calfskin design, minimalist lacing closure, and round toe. Team with camel-colored chinos or dark-wash denim to complete the look. 

Clarks Desert Boot

Clarks Desert Boots have a cult following as some of the best casual shoes for men in existence. Inspired by a 1950s design hailing from Cairo, this boot has been the favorite of beatniks, mods, Britpop bands, and basically anyone who knows a thing or two about looking cool. Expect clean lines, understated lacing, a sustainably sourced crepe sole, and an instantly recognizable silhouette. 

Best for: The OG desert boot, featuring every element we demand from the style.

Doucal’s Chukka Boot

Looking for a slightly more upmarket approach to the ultra-casual Chukka boot? Doucal’s has you covered with this ankle chukka boot made from a delectable beige shade of leather (although it’s also available in brown) and a chunky rubber sole that lends the boot a more sophisticated vibe—ideal for garden parties and other special summer occasions.  

Best for: The classic Chukka gets a 5-star upgrade.

Tod’s Gommino Chukka Boot

On the hunt for a pair of men’s ankle boots with more sartorial cachet than the standard desert boot? Our top pick would be Tod’s Gommino Chukka Boots. We can’t think of an outfit that wouldn’t immediately be enhanced by these shoes. They feature the brand’s celebrated gommini rubber soles and a buttery leather lining so no break-in period is required. They’re some of the most comfortable shoes for men as well as being a great pick for those on the hunt for casual work shoes. 

Best for: Discreet and wonderfully dignified Chukkas by these champions of understated cool. 

Slip-Ons

Life can sometimes feel like one long to-do list. Opt for a pair of slip-ons and eliminate the need to do your laces every time you leave the house. Slip-ons are undemanding, uncomplicated, and their style appeal is often underestimated. We’re giving unequivocal endorsement to these advocates of easygoing elegance. From lounge-appropriate slip-ons to summer-ready sandal alternatives, here’s how the slip-on could transform your wardrobe. 

Allbirds Tree Loungers

Another pair of all-purpose crowd-pleasing casual shoes by Allbirds, the Tree Loungers are the lace-free favorites of those seeking the top sustainable and best everyday shoes for men. They’re machine washable, for one thing. And the eucalyptus tree fiber material is not only responsibly sourced but also odor-minimizing—exactly what we need when going sockless in summer. Like all Allbirds shoes, they’re also impressively comfortable with a flexible fit that conforms to our foot’s movement as we stroll. 

Best for: Worry-free and walking-friendly weekend attire.

Castañer Espadrilles

What happens if you take the effortless style of a sandal and add the structure and sophistication of a loafer? You get these classic canvas espadrilles by family-run label Castañer—the perfect sunshine-ready addition to your summertime outfit (although we can imagine wearing these on warmer spring days too). Team with tailored trousers and a shirt for a smarter vibe or with shorts and your favorite T for the ultimate taking-it-easy attire. 

Best for: Nautical-inspired footwear that makes us nostalgic for every beach holiday ever.

Vans Slip-Ons

Van’s OG Classic LX Sneakers are the archetypal casual shoes—the footwear equivalent of that dude you know who’s so laid-back he’s basically horizontal. In fact, they were originally a favorite among surfers. So channel some carefree beach-bum vibes with these durable canvas shoes that are great for walking but equally appropriate for putting your feet up too. They’ve got all the advantages of the best sneakers for men—minus the laces. 

Best for: An iconically casual silhouette as beloved by wave-hunters and sun-seekers.

Buyers guide: how to choose a pair of casual shoes for men

Having lots of options is great but it makes deciding a headache. So what should you consider when trying to choose between all the best men’s casual shoes? 

Style

The first step in deciding on a pair of casual shoes for men is to work out when you want to wear them and how often. 

There are shoes that are more appropriate for business casual, smart casual, and general weekend wear. If you plan to wear them regularly, you’ll want casual shoes that are optimized for comfort and durability. 

In our guide to the best casual shoes for men, we included a selection of different styles. Here’s a recap:

• Sneakers – the best casual sneakers for men are ideal for wearing at the weekend. You could also wear them to work if yours is a particularly laid-back office. If you want to work out in your sneakers, look for a pair with support and cushioning. Otherwise, we recommend opting for classic sneakers in white or black leather. 
• Boat shoes – these preppy shoes are perfect for summer and spring with their minimalist lacing and rubber sole. Wear them on the beach, on holiday, but never with socks. 
• Loafers – these laceless leather or suede shoes have a slipper or moccasin-like quality, except with more of a heel. They’re both casual and elegant at the same time, ideal for occasions where you want to be well-dressed without looking like you tried too hard. 
• Brogues and Derbys – some of the best business casual shoes for men, these are more formal than the other styles here. Typically made from leather, they may feature perforations around the upper in the case of brogues. They’re perfect for the office, bar, or restaurant, and even for some semi-formal occasions.
• Driving shoes – these cool shoes for men were originally designed for driving sports cars but today are a great casual choice for men seeking something with romance and intrigue. 
• Ankle boots and Chelsea boots – if you’re looking for something appropriate for winter, you need a pair of hard-wearing boots. Chelsea boots are versatile, timeless, and comfortable. You could also explore combat boots too. 
• Chukka boots – these are ideal for transitional dressing as they’re both summery and winter-appropriate simultaneously. Lightweight and relaxed, they usually have a soft crepe sole and a few eyelets, offering trend-transcending minimalist appeal. 
• Slip-ons – the perfect choice for holidays and weekends when you can’t be bothered to do laces, the best men’s slip-on shoes are comfortable, easygoing, and supportive. 

 Material

The best material for men’s casual shoes depends on the purpose. Do they need to survive the rain? Then you want something water-resistant like leather. Looking for something more appropriate for summer? Opt for suede or synthetics. 

There’s also a whole range of innovative sustainable materials from brands like Allbirds, who make casual shoes for men from merino wool and eucalyptus tree fiber. 

 Other features to consider

• Outsole – if you want extra grip when it rains, look for treaded anti-slip rubber soles. 
• Midsole – an EVA midsole provides extra cushioning and comfort and is a staple in most sneakers. 
• Pull tab – these are often found in Chelsea boots and make it easy to get your shoes on and off. 
• Machine washable – some of the best sneakers for men are machine washable, which makes them extra low maintenance. 

 Budget

Finally, consider your budget before buying a pair of men’s casual shoes. How much can you afford? Remember that a higher price tag often means higher quality so you could consider it an investment. However, sometimes you’re simply paying for the designer logo. 

Frequently asked questions about men’s casual shoes