I’m currently at my desk, eyeing my filled shoe closet across the room. At first glance, nothing really looks too casual: pointed-toe ankle boots with stacked heels, wedge-toe oxfords, shiny monk straps and cleated winter boots are in abundance. When I tilt my head further, scanning the second-to-last, tallest shelf, I see my collection of sneakers squeezed like Thanksgiving stuffing into a turkey. Below is a row of my casual shoes, an assortment of desert boots, Chelsea boots, and a whole bunch of loafers, also stuffed like a ball of butter. With all the pieces I own, it’s the options for these shelves that are the most accessible, the ones that I reach the most.
The best casual shoes provide ease and comfort. Whether worn in the office, on walks in the park, at the bar, at the gym, or just around the house, these are the kind of styles that don’t require too much thought. You can save all that mental energy for corporate functions, state dinners, weddings at the St. Regis, and other hard-and-fast events: the stuff at the very top of my closet, the stuff I I keep at a distance.
Lately I have been alternating between my Hoka One One Bondi L shoes and my New Balance 990s. They are the best casual shoes I own which is why they are currently on the doorstep ready to take me to any destinations imaginable without any problem. And I’ve also collected some fantastic options that have had the same place of honor, out of that plush closet. So check out one or more of the styles below and rest assured your shoe game will be up to snuff.
Maverick shoes
Founded by industry veteran Rommel Vega, Holo Footwear is a brand committed to delivering durable styles with character that are designed to be lightweight and breathable, like the Maverick here.
Club C Revenge Vintage Shoes
About a century after its creation in 1895, Reebok released the Club C, a sneaker originally intended for the tennis courts but now made for wherever and wherever your feet take you. It’s the kind of style that will last for ages.
Stan Smith ‘End Plastic Waste’ Shoe
From fashion shows to tennis courts to the streets of the world, this sneaker dominates. It would be wise to pick up a pair, if you haven’t already, because like the man whose name it bears, the style is the crème de la crème. And if that doesn’t sit well with you, the fact that this particular SKU is made of Primegreen (a high-performance recycled material) should.
Chuck 70 Hi Shoe
Of all the shoes in history, it is perhaps the Converse the Chuck 70 that is the most updated, redesigned and reissued. That’s because the style serves as the perfect blank canvas, allowing anyone with the imagination to create freely without breaking the enduring mold, literally.
wool runners
Since its launch in 2017, the Allbirds Wool Runner has been a consistent bestseller for the DTC label, astounding many sneaker lovers. But what it lacks in sneakerhead cachet, it more than makes up for in durability, performance, style, and comfort. It’s reliable. And that’s damn important.
Boston suede mules
The mule has a moment. And the ultimate trainers definitely qualify as a go-to casual choice, whether you’re headed out for a quick coffee or, depending on your job, a long day at the office.
Sonoma Suede Chelsea Boot
If you’re looking for an easy style flex that won’t break the bank, look no further than New Republic’s famous boot.
Authentic original 2 eyelet boat shoes
When it comes to boat shoes, nothing – and we mean nothing-is more authentic than a pair of Sperry.
Air Force 1 ’07 Shoes
There are sneakers, and then there is the Air Force 1. It was the mack daddy, the one who started a movement, the one who elevated sneakers to the realm of collectibles. And it’s also very comfortable, so if you don’t have a pair yet, be sure to deal with that stat.
1461 3-Eyed Gibson
Tough as nails but gentle on your feet thanks to the good doctor’s signature bouncy soles. A killer combo for any casual shoe, and even better when it’s a true classic like the 1461.
Logan Flat Strap Weejuns
The world wouldn’t have been the same without GH Bass & CO. and his invention: the penny loafer (née Weejuns).
990v5 running shoe made in USA
Speaking of dads, no other shoe symbolizes fatherhood more than the New Balance 990. From comfort to easy looks, this is truly a hassle-free shoe that should be embraced by the whole family.
desert boot
Whether it’s spring or fall, the desert boot is a surefire option for between seasons thanks to its simple, versatile silhouette and lightweight construction. And it really doesn’t get any better than Clarks.
Bondi 7 shoe
Don’t let the chunky and somehow clumsy silhouette fool you, because the Hoka One One Bondi 7 (actually the brand’s collections en masse) is supremely comfortable. Indeed, when it comes to walking for miles and miles, this style is as good as it gets.
Legend Z shoe in Italian leather
Crafted from Italian Napa leather, Good Man Brand’s low-top shoes definitely have an edge. Additionally, three percent of the proceeds from each purchase will be donated to the Why Not You Foundation, an NGO that empowers and prepares children to become the leaders of tomorrow.
510 original
You’ll want to wear them absolutely everywhere. Trust your instincts and do just that.
Peppo suede and leather shoes
Mephisto: The go-to brand for dedicated mall walkers and savvy, stylish guys who see them go for miles and think, “Damn, these guys know what’s going on.” Because when it comes to casual shoes that are incredibly comfortable, these guys really know what’s going on.
Berle Leather Penny Moccasins
The timeless black loafer has graced the feet of some of the most stylish men in history, and To Boot New York has a pair that will put you on that list.
barry samaha
Barry Samaha is the style business editor at Esquire, where he covers all things fashion and grooming.
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