I’m currently at my desk, eyeing my packed shoe closet across the room. At first glance, nothing really looks too casual: pointed-toe ankle boots with stacked heels, platform wingtip oxfords, shiny monk straps, and lugged winter boots are in abundance. When I tilt my head further, scanning the penultimate shelf, the largest shelf, I see my collection of sneakers pressed like Thanksgiving stuffing in a turkey. Below that is a row of my casual shoes, an assortment of desert boots, Chelsea boots, and a whole lot of loafers, also stuffed like a Butterball. With all the pieces I own, it is the options in those shelves that are the most accessible, the ones I reach for the most.
The best casual shoes impart ease and comfort. Whether they are worn in offices, to walks around the park, to the bar, to the gym, or just around your home, these are the kind of styles that don’t require too much deliberation. You can save all that mental energy for corporate functions, state dinners, weddings at the St. Regis, and other hard-and-fast black-tie events: the stuff that sits at the very top of my closet, the stuff that I keep at a distance.
Lately, I’ve been rotating between my Bondi L shoes by Hoka One One and my New Balance 990s. They are the best casual shoes I own, which is why they’re currently by the door, ready to take me to every conceivable destination with no fuss. And I’ve also gathered some fantastic options that have had the same pride of place, out of that stuffed closet. So check out one or more of the styles below, and rest assured that your shoe game will be up to snuff.
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Founded by industry veteran Rommel Vega, Holo Footwear is brand committed to offering sustainable styles with character that are constructed to be lightweight and breathable, like the Maverick right here.
Club C Revenge Vintage Shoes
About a century after it was founded in 1895, Reebok launched the Club C, a sneaker initially intended for tennis courts but that is now made for everywhere and anywhere your feet will take you. It’s the kind of style that’ll last for centuries to come.
Stan Smith ‘End Plastic Waste’ Shoe
From fashion runways to tennis courts to streets far and wide, this sneaker dominates. You’d be wise to cop a pair, if you haven’t done so already, because like the man it’s named after, the style is the cream of the crop. And if that doesn’t get you, the fact that this particular SKU is made of Primegreen (a performance recycled material) should.
Chuck 70 Hi Shoe
Of any shoe in history, it is perhaps the Converse the Chuck 70 that gets updated, reimagined, and reissued the most. That’s because the style serves as the perfect blank canvas, letting anyone with imagination create freely without breaking the durable mold—literally.
Since its launch in 2017, the Allbirds Wool Runner has been a consistent best-seller for the DTC label, astounding many sneaker fiends. 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 is having a moment. And the ultimate shuffling-around shoes definitely qualify as a go-to casual choice, whether you’re heading out for a quick coffee run or, depending on your job, a long day at the office.
Sonoma Suede Chelsea Boot
If you’re in the market for an easy style flex that won’t break the bank, look no further than New Republic’s celebrated boot.
Authentic Original 2-Eye Boat Shoes
When it comes to boat shoes, nothing—and we mean nothing—is more authentic than a pair by Sperry.
Air Force 1 ’07 Shoes
There are sneakers, and then there’s the Air Force 1. It is the mack daddy, the one that started a movement, the one that elevated sneakers into the realm of collectibles. And it’s also mighty comfortable, so if you don’t have a pair yet, make sure to cop this guy stat.
1461 3-Eye Gibson
Tough as nails but kind to your feet thanks to the good doctor’s signature bouncing soles. A killer combo for any casual shoe—and even better when it’s a bona fide classic like the 1461.
Logan Flat Strap Weejuns
The world would not have been the same without G.H. Bass & CO. and its invention: the penny loafer (née Weejuns).
990v5 Made in US Running Shoe
Speaking of daddies, no other shoe symbolizes fatherhood more so than the New Balance 990. From the comfort to the easy look, this is truly a no-fuss shoe that should be embraced by all the in family.
Whether it’s spring or fall, the desert boot is a foolproof option for in-between seasons thanks to its easy, versatile silhouette and lightweight construction. And it really doesn’t get any better than Clarks.
Bondi 7 Shoe
Don’t let the sizable, sort-of clunky silhouette fool you, because the Hoka One One Bondi 7 (actually, the brand’s collections en masse) is extremely comfortable. Indeed, when it comes to walking for miles and miles, this style is as good as it gets.
Italian Leather Legend Z Shoe
Made from Italian Napa leather, Good Man Brand’s low-tops most certainly have edge. In addition, three percent of the proceeds from each purchase will be donated to the Why Not You Foundation, an NGO that empowers and prepares kids to become the leaders of tomorrow.
You’ll want to wear them absolutely everywhere. Trust your instincts and do exactly that.
Peppo Suede & Leather Shoes
Mephisto: the go-to brand for dedicated mall-walkers and the savvy, stylish guys who see them putting in the miles and think, “Damn, those dudes know what’s up.” Because when it comes to casual, crazy-comfortable shoes, those dudes really do know what’s up.
Berle Leather Penny Loafers
The timeless black penny loafer has graced the feet of some of the most stylish gents in history, and To Boot New York offers a pair that’ll get you on that list.
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