An assortment of boots Courtesy of the brands

The 36 Best Men’s Boots to Get You Through Fall and Winter

We laced up in countless pairs, from Chelseas and Chukkas to Snow and Combat boots, and field-tested them. These are the ones to get.

With foliage turning and flip-flops rightfully banished to their lairs, all signs point to a return to boot-wearing. And how better to mark the return of boot season than to find—and field test—the best boots for men across nine categories ranging from chukkas to hikers, desert boots to work boots? After many miles of pavement pounding and more than a few blisters, we’re happy to share the results below.

But first, a note on testing: Once we found our top picks, I requested samples from each of the makers. In the instances in which I was permitted to wear the samples outside rather than return them, I subjected each pair to an hour of continuous wear on city streets. In the weeks that followed, many saw additional wear.

As the experience of even the best-made shoes will vary radically based on the user’s feet, I felt I should provide a note on my own. My feet are rather hard to fit, as the right is an 11US on the Brannock Device while my left is a 12. As a result, I take a 11.5US in sneakers. And while I wear a D width, my feet are wider at the toes. Podiatric particulars aside, here’s the best of what I wore along with a few honorable mentions in each category.


Carmina Simpson Boots

carmina black leather chelsea boots

The Rake

Considering its Swinging Sixties heritage, the Chelsea is a style of boot that should look sexy. Carmina delivers on that front with a model featuring a raised profile and a long, slightly squared-off toe. It’s as sleek and elegant as a Chelsea comes, which made me fear it’d be a horror on my not-so-sleek feet. However, the boots—which are also remarkably lightweight—proved comfortable from the start, with the only issue being a slight pinch on my left foot that dissipated after 10 minutes (I took their website’s advice and went up a half-size to an 11UK). With wear, I also learned that they could look casually rakish under a suit.

Buy Now: $525

Runners Up:

Ralph Lauren Purple Label Penfield Chelsea Boot

Ralph Lauren Chelsea boot

Ralph Lauren

Buy Now: $1,250

Saint Laurent Wyatt Suede Chelsea Boots

Saint Laurent chelsea boot

Saks Fifth Avenue

Buy Now: $945

R.M. Williams Signature Craftsman Boot

R.M. Wiliams Chelsea boot

R.M. Williams

Buy Now: $795


Wolverine 1000 Mile Plain-Toe Boot

Wolverine 1000 Mile Boot


Work boots tend to fall into two categories: “heritage” and “heritage-inspired.” In production for more than a century, Wolverine’s 1000 Mile Boot fits squarely into the former category. Out of the box, I was struck by the richness of its Horween Chromexcel leather: It’s beefy but pliant, with an oiliness that made it surprisingly flexible from the first wear. I went down a full size to a 10.5US, which still left plenty of room for thick socks. After about a half-hour they began to pinch around the instep on each foot, though I imagine the leather will soften and expand with wear. A fair amount of their comfort is derived from the boot’s bulbous, reinforced toe, which is far from sexy but feels like a protective dome. It’s what I’d want guarding my toes in the instance of, well, actual work.

Buy Now: $385

Runners Up:

Church’s Coalport Leather Derby Shoes

Church's boots


Buy Now (MATCHES): $790

Buy Now (CHURCH'S): $1,050

Common Projects Combat Leather Derby Boots

Common Projects combat boot

Mr Porter

Buy Now: $650

Red Wing Shoes Iron Ranger

Red Wing boots

Red Wing

Buy Now: $329


Diemme Roccia Vet Ankle Boots

Diemme boots

Saks Fifth Avenue

Hiking boots have trekked from the trailhead to the runway in recent years, and Diemme’s Roccia Vet has a foot in both worlds. It strikes the right balance between rustic and urbane with speed hook eyelets, a heavy treaded sole and a sleek leather upper. That leather is thick yet pliant where it counts, and its padded ankle and inner lining swaddle the foot in soft, insulated comfort. Though I didn’t have the chance to wear it in anything approaching cold weather, I could imagine it keeping my toes toasty through below-freezing temps. The Roccia Vet is not something I, personally, would wear on an actual hike, but I would count on it to take me 30 blocks in a blizzard.

Buy Now: $429

Runners Up:

John Lobb Alder Leather Boots

John Lobb boots


Buy Now: $1,980

Scarosso Edmund Boots

Scarosso boots


Buy Now: $385

Danner Mountain Light Boot

Danner boot


Buy Now: $379.95


Crockett & Jones Tetbury Calf Boot

Crockett & Jones boot

Todd Snyder

The chukka is a slippery category to define, but at its most generous includes any ankle-height boot with two-to-three eyelets. They can vary wildly in formality, but Crockett & Jones’s Tetbury is decidedly a dress chukka, distinguished by a waxed calfskin upper and a square, extended toe. My 10.5UK pair felt a bit large at first with thin cotton socks, yet there was a satisfying feeling of suction when I stepped in—this is a boot expertly contoured to the shape of the foot. Though I experienced heel slippage at first, the issue subsided as they broke in. The Tetbury is made on the brand’s 348 last, which allows for an extra inch of space at the toe and took some getting used to but did not impact the overall fit. I also appreciated its thick Dainite sole, which gives it a “town and country” feeling without detracting from its dressy appeal.

Buy Now: $650

Runners Up:

Santoni Bohemian Derby Shoes

Santoni boots


Buy Now: $680

Tod’s Suede Desert Boots

Tod's boot


Buy Now: $625

Alden Chukka Boot

Alden boot


Buy Now: $577


Drake’s Clifford Desert Boot with Rubber Sole

Drake's boots


Desert boots are best understood as a sub-genre of the chukka, with two distinct characteristics: a lower, two-eyelet profile and a crepe sole. The standard model of the Drake’s Clifford boot fulfills both criteria, but the company also makes a roughout suede version with a Dainite-esque rubber sole. I was attracted to this rule-breaking variant, as crepe soles can wear out quickly and can’t be replaced—an issue that felled the several pairs of Clark’s Desert Boots I wore in college. This Clifford’s roughout suede proved exceptionally beautiful in-person, with a warm, saturated hue and a velvety texture. That buttery suede, combined with the boot’s unlined construction, provided soft comfort from the start, even if the left in a 10.5UK felt snug at first and blistered after a full day of wear (afterward, I wore them at home for a few hours with thick socks to expand the fit, which seemed to do the trick). I particularly enjoyed how their profile, which is similar to but lower than the Astorflex Greenflex, complemented cuffed trousers and tailoring.

Buy Now: $455

Runners Up:

Astorflex Greenflex

Astorflex boots


Buy Now: $195

Clarks Desert Boot

Clark's boot


Buy Now: $150

Sanders Marvin Tobacco Reverse Suede Chukka Boot

Sanders boot


Buy Now: $243.58


George Cleverley Leather Toby Derby Boots

George Cleverley boots

Mr Porter

With a tall shaft and a pebble-grained upper, Cleverley’s Toby boot is built like a tank but looks like a dress shoe. With a more sculpted shape, I found it snug in a 10.5 UK with cotton boot socks but fine with thin dress socks—appropriate, considering its dress boot status. It broke in more comfortably than your average pair of dress shoes, and I appreciated the extra space provided by its squared-off toe. And while similar in appearance to cordovan, the cavalry calf was less stiff around the edges but did form rolling, cordovan-like creases after an hour’s walk (a positive in my book). Extra points were awarded for its Dainite sole, which delivered great grip from the offset but appears like a formal leather sole from all sides.

Buy Now: $825

Runners Up:

Tricker’s Stow Full-Grain Leather Grain Boots

Tricker's boots

Mr Porter

Buy Now: $640

Beckett Simonon Elliot Balmoral Boots

Beckett Simonon Elliot Balmoral Boots

Beckett Simonon

Buy Now: $239

Joseph Cheaney & Sons Hanover Balmoral Boot

Joseph Cheaney & Sons Boots

Joseph Cheaney & Sons

Buy Now: £454.17


Brunello Cucinelli Padded Ankle Boots

Brunello Cucinelli Padded Ankle Boots


There are winter boots made for sloshing through half-melted snowbanks with impunity—like shearling-lined L.L. Bean boots—and winter boots made to keep you warm while looking good. Cucinelli’s padded ankle boots are in the latter grouping and fulfill both its aims. While I wouldn’t stick them ankle-deep into slush, I would wear them under grey flannels and a topcoat in 20-degree weather. In a 44.5 they felt comfortably snug with thick socks, and the felt fabric padding at the ankles provided welcome—and warm—cushioning.

Buy Now: $1,295

Runners Up:

Mackage Hero Lug Sole Shearling-Lined Winter Boot

Mackage Hero Lug Sole Shearling-Lined Winter Boot


Buy Now: $650

L.L. Bean Shearling-Lined Boots

L.L. Bean Shearling-Lined Boots

L.L. Bean

Buy Now: $230

Moncler Vancouver Tricolored-Sole Boots

Moncler Vancouver Tricolored-Sole Boots


Buy Now: $750


Grenson Easton Boots

Grenson Easton Boots


Hunting boots are loosely defined as mid-height boots with a moccasin-stitched toe. Though readily identified with made-in-Maine brands like Quoddy or Yuketen, Grenson makes a bang-up number in Northampton. Their Easton is crafted from a soft and flexible natural grain leather that feels broken-in from the first step and is attached to a chunky rubber commando sole that suits it to concrete despite its campground looks. While their sizing guide advised going up half a size, I wish I’d stuck with my true 11.5—its round apron toe felt particularly roomy, even with thicker socks.

Buy Now: $460

Runners Up:

Yuketen Angler Boots with Cortina Sole

Yuketen Angler Boots with Cortina Sole


Buy Now: $662

Quoddy RL Camp Boots

Quoddy RL Camp Boots

J. Crew

Buy Now: $350

Sperry Authentic Original Lug Chukka

Sperry Authentic Original Lug Chukka


Buy Now: $149.95


Edward Green Camden Chelsea Boot

Edward Green Camden Chelsea Boot

The Rake

This last category is intentionally vague, meant to net Chelsea boots, jodhpurs, traditional moto boots and more, unified by a single factor: a low ankle-height (and perhaps, the ability to envision them being worn by Steve McQueen). Amid this diverse field, Edward Green’s Camden Chelsea boot emerged as a star. It’s made from Utah delapré, a waxed French leather with a crinkled pattern that broke into endearing wrinkles with wear. The leather was exceptionally soft, resulting in what may have been the easiest break-in process I’ve ever experienced. My 11UK truly fit like a glove—firm enough to prevent any slippage, yet with plenty of give—and had a remarkable lightness that should make it an ideal travel boot. While casual by nature, the slimness of its rubber sole added enough dress appeal to match with suits.

Buy Now: $1,470

Runners Up:

Doucals Tronchetto Fibbia Boots

Doucals Tronchetto Fibbia Boots

Saks Fifth Avenue

Buy Now: $500

Belstaff Trailmaster Suede Boots

Belstaff Trailmaster Suede Boots

Mr Porter

Buy Now: $395

Frye Conway Harness

Frye Conway Harness


Buy Now: $368

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