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.

Runners-Up

Allen Edmonds Tanner Weatherproof Chelsea Boot

Sid Mashburn Chelsea Boot

Carmina Simpson 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.

Runners-Up

Viberg Service Boot 1035

Red Wing Shoes Iron Ranger Boots

Aquaitalia Bernardo 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.

Runners-Up

Scarosso Edmund Boots

Danner Mountain Light Boot

Chukkas tens to come in two flavors: the highly casual, quasi-desert boot style best for kicking around with jeans, or the smarter and more chiseled variety you might pair with say, trousers and a turtleneck. The uncreatively named Morjas Chukka boot splits the difference between these two genres nicely with its clean, slightly higher topline and three-eyelet silhouette, a generously rounded toe that has the faintest hint of an almond shape and a Goodyear welt that sits close to the shoe itself. Further upping its versatility is a studded rubber sole that’s much smarter than a crepe but carries the same benefits of slip-resistance on slick streets (crucially, this means you can also walk through road salt without damaging the soles). In sum, it’s what an chukka should be: a footwear jack-of-all trades.

Runners-Up

Prada Suede Chukka Boots

Officine Creative Frame 002 Chukka Boots

Mr. P Lucien Suede Chukka 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 Clifford’s 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.

Runners-Up

Santoni Suede Desert Boot

Clarks Desert Boot

Todd Snyder Nomad Boots

In my personal experience, balmoral boots have been tricky. In isolation, they certainly look cool, with their dramatic height and artful broguing. But when I put them on, I’m reminded that I’m not a member of the Peaky Blinders cast, and I just can’t figure out how they might be worked into my rotation. Which is why John Lobb’s Alder is such a breath of fresh air. Perhaps more balmoral-inspired than capital-B Balmoral, they’re based on a pair of WWII-era ski boots in the Lobb archives and have a sportier touch with their speed hook eyelets and cushioned collar (which on a non-aesthetic note, makes them extremely comfortable). Ditching the broguing eliminates the costume factor, allowing its sporty yet clean design to pair with smarter outfits and perhaps even tailoring, if you’re in a Gianni Agnelli type of mood. Lastly, a water-repellent finish, storm welt and a heavy-duty rubber sole remind you that as fetching as the Alder is, it’s not just for show.

Runners-Up

Tricker’s Stow Full-Grain Leather Grain Boots

Beckett Simonon Elliot Balmoral Boots

There are plenty of styles today that have that hunting boot look—rawhide laces, moccasin-stitched toe, substantial outsole—but that you know are destined for hikes to only Whole Foods and Starbucks. But this pair from Maine maker Quoddy looks and feels like something you could take to the trail, with a treaded Vibram outsole and a leather upper that’s been made naturally water resistant thanks to its conditioning with unrefined oils. In full disclosure, I have not in fact worn these into the woods—because I live a lot closer to a Whole Foods than a trailhead—but they feel like the sort of boot that can handle going off-road, and just as importantly, look all the better for doing so. I was a bit surprised on sizing: the 11D I received fit snugger that I expected, and in retrospect I may have wanted to size up to an 11.5D to wear it with thicker socks.

Runners-Up

Yuketen Maine Guide 6 Eye Leather Boots

In my personal view, few items nail form and function so well as the L.L. Bean Boot. I own them in about every height and variety that exist and have been known to sport them with black tie when the weather insists (while carrying a pair of velvet slippers to change into later, of course). But my Bea collection had a gap: a proper cold-weather iteration, as my own feet have gone numb in my original-design Bean Boots on more than one freezing occasion. So, I was quite excited to test out the shearling-lined version, which aside from its genuine lamb fur insulation, also boasts a slightly higher, 10” topline and a substantial-feeling tumbled leather upper. Within days of receiving them, my native Boston provided a string of single-digit days for proper testing, and I am happy to report that my toes retained their feeling throughout. Helpfully, the higher topline made it easy to tuck my jeans into the boot, which aside from allowing for a cleaner look, saved my denim from being splashed with slush. And only after a few foul-weather wears, the leather has begun to patina beautifully. Just note that like all Bean Boots, these run big: I sized down to a 10D, which still left plenty of room for my thickest socks.

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.

Runners-Up

Billy Reid Paglia Moto Boot