What loafers are to the warmer months, boots are to fall and winter. Along with enveloping coats and swaddling sweaters, boots mark the changing of the seasons as accurately as any equinox. It’s not just a stylistic choice—these are shoes engineered to keep your soles cozy come rain, sleet, snow or polar vortex.
While a sleek pair of Chelsea boots are a wardrobe staple, hardier styles are designed to endure the most inclement weather. When shopping with the elements in mind, look for models with Goodyear welted soles (stitched in such a way to ensure water doesn’t seep in and lead your boots to an early retirement) and ultra-durable full-grain leather. But of course, we don’t all live in places with such seasonal concerns. If you’re in that lucky camp, there are even more options to be enjoyed year-round. We’ve selected 11 of the best pairs available now—from lightweight desert boots to rugged combat styles—for a guide to the boots that every man should have in his footwear arsenal.
-
Scarosso ‘Enzo’ Chelsea Boots
Image Credit: The Rake If there’s only one pair of boots in your closet, make it a refined set of Chelseas. Although the design dates back to the Victorian era, it really hit its stride in the swinging ’60s when all of London’s coolest cats—think Bowie and the Stones—were sporting them in Chelsea (get it?). Scarosso’s nod to that era with a streamlined profile and tapered toe that will add just the right note of grooviness to a sharply tailored suit.
-
Saint Laurent ‘Wyatt’ Suede Chelsea Boots
Image Credit: Ssense For a more laidback take on a Chelsea boot, look to Saint Laurent’s slick iteration in tan suede. With an ever so slightly pointed toe and stacked leather heel, they’ve got a hint of Johnny Cash rocker to them—best paired with black jeans and dark shades.
-
Clarks ‘Wallabee’ Boot
Image Credit: Todd Snyder Clarks’s classic Wallabee boots have one of the most colorful histories in all of men’s footwear: designed in England, based on a German moccasin, the style first took off in Jamaica in the late 1960s. It went on to become a favorite of the ’80s New York rap scene (Wu-Tang were fans) and, eventually, the fashion set. The shoe’s broad appeal is thanks to its versatility: somewhere between a sneaker and a proper boot, it can be dressed up or down.
-
John Lobb ‘Alder’ Leather Boots
Image Credit: MyTheresa It’s not easy to look elegant while fighting off the elements, but John Lobb’s Alder boot does just that with remarkable grace. Inspired by an archival ski shoe, it features a hardy, Goodyear-welted, rubber lug sole and full-grain upper. And yet the proportions and first-rate finishing make this hard-wearing boot polished enough to wear with a flannel suit.
-
Diemme ‘Roccia Vet’ Boots
Image Credit: Ssense With their padded tongue and collar and hi-vis laces, Italian brand Diemme nods to real deal work boots. But don’t be fooled by their rugged looks—these are crafted with luxury in mind. They’re perfectly insouciant with tailored trousers and will also look good with denim of any hue.
-
Crockett & Jones ‘Coniston’ Boot
Image Credit: Crockett & Jones Although this boot counts such utilitarian details as storm-welted rubber soles and full-grain uppers, the handsome design belies that practicality. In other words, these are an ideal go-anywhere boot. They’re constructed to endure foul weather but would not look out of place in the boardroom.
-
Church’s ‘Colbury’ Chelsea Boots
Image Credit: MyTheresa For a rakish twist on traditional Chelsea boots, this model combines a chunky rubber sole with dapper brogue detailing—a winning mash-up of city and country footwear classics. Inherently smart-casual, these boots are perfect for pairing with relaxed tailored clothing: trousers, knits, unconstructed jackets.
-
Carmina Suede Chukka Boots
Image Credit: The Rake Chukka boots’ roots are in the military (they were first popularized by British soldiers in balmy colonies,) which explains their easy wearability. While chukkas tend to skew casual, Carmina’s are a smarter alternative thanks to their elongated vamp and chiseled, semi-square toe.
-
Common Projects Combat Boots
Image Credit: FarFetch This fall, there’s a trend toward all things chunky and treaded in footwear—a look that’s definitely cool but can quickly go wrong. The key is finding a balance that’s chunky but not clunky, like this sleek riff on combat boots in polished calfskin. Truer to military styles than punky Dr. Martens, these boots will work with everything from selvedge denim to tweed trousers.
-
Tod’s Rubber Sole Desert Boots
Image Credit: Tod's Desert boots can be enjoyed year-round as a more casual alternative to traditional derbies or oxford lace-ups. This pair from Tod’s is one you’ll be turning to year after year thanks to the timeless mid-brown suede, almond toe and comfortable rubber sole.
-
Carvil Ankle Boots
Image Credit: The Webster If you’re in the mood for something with a bit more kick, Cuban heels are having a comeback. Back in the ’60s, Bob Dylan and Alain Delon got theirs from Parisian brand Carvil—and you can too. This style, named for Dylan, combines a stacked heel, zip closure and slightly pointed toe for pure midcentury cool.
