Men’s casual shoes is a pretty fuzzy category. It covers everything from blue suede moccasins to leather sneakers and black penny loafers. Almost any shoe can be casual with the right styling. Chukka boots with a blazer and slim-fit dark jeans says ‘date night’; chukkas under some green chinos and a white tee says ‘weekend roadtrip’. Casual is really just a state of mind.
The rise of the ‘casual shoe’ started after 1945, when new styles and cheaper manufacturing techniques made shoes more accessible for the average guy in the street. Sneakers and high-top trainers came along in the ‘70s, then Doc Martins and lace-up combat boots, before an explosion of popular styles in the ‘90s and early ‘00s.
Today there are dozens of different shoes that could fall under ‘casual’. But here we’re going to run through the best men’s casual shoes, the most popular styles, and when to where them.
Casual doesn’t mean cheap
If we could offer one piece of advice, it’s this: invest in your casual shoes. They really matter. And not just for chiropractic reasons. Your shoes define your entire outfit—from the ankle up. As Hardy Amies famously said, “It is totally impossible to be well-dressed in cheap shoes.” So when it comes to men’s casual shoes, think in terms of style, rather than budget. Spending a little more for some well-made sneakers with a full leather upper will save you money in the long run, especially if you look after them. Here’s a crash course in shoe care, if you need some tips.
Casual shoes for the weekend
Obviously the weekend is when men’s casual shoes really come into their own. There are no hard and fast rules here. You should wear whatever suits the season and makes you feel comfortable. During the colder months, look for more durable, heavy styles, like our INGRAM military boots or DAYTON khaki Chelsea boots. In spring and summer, keep things light and breezy. Maybe our DELUCA navy driving shoes, or some well-made strap sandals, like the SIERRA. If you’re looking for something versatile, you can’t go wrong with ankle-high men’s Chukka boots. Chukkas look sharp in bars or boardrooms, under chinos or jeans. They’re probably your most flexible casual shoe.
Casual shoes for the office
A lot of workplaces have relaxed their dress code in recent years, especially after the pandemic. Oxfords and brogues are no longer compulsory, and you should feel free to experiment with men’s casual shoes (maybe, you know, run things by your boss first). Our favourite casual style for the office is definitely the humble Chelsea boot. You can play things safe with a classic black leather Chelsea, like the BEAUMONT, or experiment with suede and nubuck. Our HARDIN Chelsea boots are definitely work appropriate, but they’ve got that textured, casual vibe you only get with suede. Just match them with navy dress chinos, a business shirt and a sharp sports jacket.
Casual shoes for walking
Walking shoes need to be durable, comfortable and weatherproof (stylish doesn’t hurt either). You need to think about materials, too. Long walks in a pair of shoes will cause your feet to sweat. You need a leather upper that will breathe and can withstand some moisture—so suede and nubuck are both out. Our SMITH leather sneakers (in tan, navy or white) are solid walking shoes. They’re made from a soft leather upper, so your ankle won’t get cut to pieces, and they’ve got cushioned heels and rubber soles. A lightweight shoe, like the WILBURN, can work too. Just don’t take them trail hiking—these guys are made for parks, not National Parks.
Casual shoes for the beach
The best casual shoes for the beach are the ones that can be slipped on and off. Being able to survive the odd accidental splash also helps. A well-made pair of sandals is a great place to start, but once you’ve nailed that, feel free to expand your collection. We recommend one pair of lightweight espadrilles and one pair of leather boat shoes—the MANLY is a great option. Round out the mix with one pair of slightly dressier beachside shoes. Maybe a woven leather loafer like the TULSA. You never know when some rich friend will invite you onto their yacht (note: if you don’t have any yacht-owning friends, find some immediately).