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 and hikers to dress and work boots? After many miles of pavement pounding and more than a few blisters, we’re happy to share the results below.
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.
Best Chelsea Boots
Considering its Swinging Sixties heritage, the Chelsea is a style of boot that should look sexy. R.M. Williams 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 with every outfit.
Best Combat/Work Boots
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.
Best Hiking Boots
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.
Best Chukka Boots
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.
Best Desert 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 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.
Best Balmoral/Dress Boots
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.
Best Snow/Winter 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.
Best Hunting 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.
Best Motorcycle/Ankle Boots
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.
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