Fall is when shoes start to matter again. Sandals and sneakers get shelved, loafers look flimsy, and suddenly, the only footwear that feels right is a boot with enough presence to cut through the chill and the crowd. In a single statement, boots are the foundation of every good fit once the thermostat dips.
Think about it: boots carry you through weather, cobblestones, spilled whiskey and the kind of nights that blur into mornings. They change your posture, give you a silhouette with gravity and keep everything else you’re wearing from drifting into “half-committed” territory. A solid boot makes a basic crewneck look styled, and turns denim into a uniform worth repeating.
The market’s never been richer. Italian ateliers are still cranking out suedes with the kind of finish you’d normally see on tailoring, while the performance guys in the Dolomites are sneaking alpine DNA into boots that can live on Lafayette Street without looking like REI inventory. Even the fashion houses that once treated footwear like an afterthought now know: you can’t bluff your way through fall without boots.
So call this the season’s true reset. Forget micro-trends and hyped drops. If you want staying power—something that’ll survive the rain, the office, the afterparty and the inevitable hangover brunch—you start at ground level. All of them chosen for one reason: they’ll earn their place in your fall rotation. You don’t need more boots. You need better ones.
The Best Men’s Boots
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Brioni Milano Suede Rubber-Sole Chukka Boots -
Morjas Suede Chelsea Boots -
Our Legacy Camion Leather Boots -
Paul Smith Lawson Suede Chelsea Boots -
George Cleverley Taron II Boot -
Officine Creative Aston Crepe 004 Suede Boots -
Bally Wently Grainy Leather Side-Zip Ankle Boots -
John Lobb Field Nubuck Leather Chukka Boots -
Diemme Ampezzo Leather Boots -
Sebago Tala Suede Boots -
Jacques Solovière Mark Boot -
Christian Louboutin Devon Lug-Sole Suede Chelsea Boots -
Danner Mountain Light -
Yuketen Suede-Trimmed Full-Grain Leather Boots -
Berluti Alessio Scritto Leather Boots -
Christian Louboutin Alpinosol Lug Sole Chelsea Boots -
Diemme Roccia Vet Boots -
Sorel Slabtown 62′ Chelsea Boots -
Roa Federa Rubber Boot -
Brunello Cucinelli Men’s Suede Chelsea Ankle Boots -
J.M. Weston Jodhpur Boot -
Manolo Blahnik Sapele Boots -
Red Wing Shoes Classic Moc Boots -
John Lobb Alder Leather Boots -
Todd Snyder Nomad Suede Chelsea Boot -
Blundstone Chelsea Boots -
Le Majordome M59 Galosh Boot -
Ralph Lauren Leather Boots -
Celine Homme Margaret Chelsea Boots
Brioni Milano Suede Rubber-Sole Chukka Boots
Chukkas usually get benched after Friday, but Brioni’s take doesn’t clock out. The Milano is crafted in Italy from calf suede that borders on decadent, and the profile skews tailored with its rounded toe, sculpted heel and zero bulk. But the kicker is underneath: a stealthy rubber sole with city grip and off-road discretion.
Brioni
Morjas Suede Chelsea Boots
The Swedes know a thing or two about understatement, and Morjas leans into it with these Chelseas. Handmade in Spain, they’ve got the suede to play nice with your fleece, yet enough rubber sole grip to keep you steady on subway grates after a wet October. They’re not trying to reinvent the wheel, just refine it, like swapping your Ikea sofa for a Carl Hansen chair.
Morjas
Our Legacy Camion Leather Boots
If a Chelsea boot went to art school and picked up a nicotine habit, it’d look like this. Our Legacy swaps out elastic for a side zip, sharpening the silhouette and dialing up the subversion. The square toe is subtly confrontational, and the Vibram sole says you don’t Uber between neighborhoods. These are boots for walking in like you own the venue (even when you don’t).
Our Legacy
Paul Smith Lawson Suede Chelsea Boots
These look classic from across the room—then you clock the rainbow tab at the heel and realize Paul Smith is still playing the long game. The Lawson boots have the softness of a jacket you “borrowed” from your dad’s closet, but they’ll hold their shape through gallery openings and dinners where you’re expected to know the wine list.
Paul Smith
George Cleverley Taron II Boot
Cleverley’s Taron II, originally designed for the Kingsman films, feels more like a prop from Savile Row’s golden age than a seasonal buy. A semi-brogue derby boot cut from coffee suede, it balances dapperness with real-world durability: storm-welted Dainite soles grip when the pavement slicks, while speed hooks make lacing up anything but a chore.
George Cleverley
Officine Creative Aston Crepe 004 Suede Boots
This is what happens when Italian sensualism hits mute. The Aston Crepe is low-volume and high-impact: unlined suede and a rubber-crepe sole. They read somewhere between artist residency and gallery director—boots for the kind of guy who claims he’s “just looking” at The Armory, but somehow walks out with a Gio Ponti chair.
Officine Creative
Bally Wently Grainy Leather Side-Zip Ankle Boots
Some boots beg for laces, others know when to skip the drama. Bally’s Wently ankle boots opt for the latter, slipping into the lineup with a clean side-zip that saves you from morning contortions. Cut from grainy calf leather, they’ve got enough texture to look broken-in without the actual wear, and a stacked heel gives them just enough lift to edge past casual.
Bally
John Lobb Field Nubuck Leather Chukka Boots
John Lobb’s Field Chukka takes the familiar two-eyelet shape and runs it through the brand’s London workshop, emerging with Goodyear welted construction that could outlive your next car lease. Cut in a brushed nubuck with a round toe and lug sole, it’s as comfortable stalking city pavement as it is trudging across a wet country lawn.
John Lobb
Diemme Ampezzo Leather Boots
Born in the Dolomites, Diemme builds boots the way Italians build ski lodges. The Ampezzo is their signature low-top: full-grain leather, mudguard trim and a platform outsole that looks as at home in Cortina as in SoHo. Wear them with corduroys on a weekend city hike, or throw them under tailored trousers when the weather makes a fool of everyone else’s sneakers.
Diemme
Sebago Tala Suede Boots
Sebago takes moccasin DNA and spins it into something sneaker-adjacent, boot-adjacent, and very fall-ready. The Tala’s suede upper sits on lightweight EVA soles, which means they feel like weekend shoes but look smart enough for Tuesday lunches.
Sebago
Jacques Solovière Mark Boot
Paris label Jacques Solovière has a habit of stripping footwear down to its purest form, and the Mark Boot is no exception. Cut from a single piece of smooth calf leather, it sidesteps the usual seams and panels for a clean silhouette. The inside zipper saves you the tug-of-war that comes with standard Chelseas, while the thick leather sole gives it just enough heft to stand its ground through fickle weather.
Todd Snyder
Christian Louboutin Devon Lug-Sole Suede Chelsea Boots
Chelsea boots aren’t usually built for mud, but Christian Louboutin wasn’t about to let hikers have all the fun. The Devon takes the sleek Chelsea profile—elastic gores, clean vamp—and drops it on a lug sole chunky enough to chew through wet sidewalks or leaf-strewn park trails. Naturally, the signature red sole flashes like a spoiler, reminding everyone these aren’t just boots, they’re Louboutins.
Christian Louboutin
Danner Mountain Light
Handcrafted in Portland, Oregon, Danner’s Mountain Light casual boots blend timeless design with modern technology. Gore-Tex lining keeps feet dry in challenging conditions, while the Vibram Kletterlift outsole provides exceptional traction on rugged terrain. At 58 ounces, they’re formidable, not fancy—much like the weekend adventures they’re built for.
Danner
Yuketen Suede-Trimmed Full-Grain Leather Boots
Yuketen’s work boots are a lesson in considered design. Full-grain leather forms the foundation, elevated by suede trim along padded collars. The pinked welts are a mark of quality construction while Vibram Morflex rubber soles offer lightweight durability and serious grip.
Yukuten
Berluti Alessio Scritto Leather Boots
Crafted in Italy from full-grain Venezia leather, each pair of these Berluti boots features the brand’s signature “Scritto” engraving. The lightly padded insoles and convenient zip fastening prove comfort and style aren’t mutually exclusive.
Berluti
Christian Louboutin Alpinosol Lug Sole Chelsea Boots
Louboutin’s Alpinosol boots are where the designer’s flair meets mountaineer grit. Available in leather and suede, they sport a lug sole that may very well help you tackle Everest (or at least that tricky cobblestone street). And let’s not forget that signature red sole—a men’s fashion power move for those in the know.
Louboutin
Diemme Roccia Vet Boots
Handcrafted in limited quantities in Onè di Fonte, Italy, Diemme’s Roccia Vet boots are a cult classic for good reason. They merge traditional Italian hiking boot design with modern, lightweight soles—equally at home on mountain trails or city streets. The built-in ankle supports aren’t just comfortable; they’re a guarantee of stability.
Diemme
Sorel Slabtown 62′ Chelsea Boots
These seam-sealed and waterproof boots are accented with two-tone leather uppers that catch the eye without shouting. The removable molded EVA footbeds and Cushgrip soles ensure comfort without compromising on grip. They’re smart enough for the business casual office, tough enough for weekend errands.
Sorel
Roa Federa Rubber Boot
Known for exceptional hiking gear, Roa knows how to make a damn good boot. The water-repellent ripstop nylon shaft, tough-as-nails Vibram soles and rubberized components create a near-impenetrable barrier against the elements. A drawstring closure and lycra sock lining ensure a snug fit. The look may be overkill for most situations…which is precisely the point.
Roa
Brunello Cucinelli Men’s Suede Chelsea Ankle Boots
Don’t let the suede fool you—Brunello Cucinelli’s Chelsea boot styles is no lightweight. Inspired by Umbrian country living but built for urban warfare, these boots armor soft suede with rubberized calfskin. The result is a perfect blend of refinement and resilience. They’ll take you from client meetings to impromptu hikes without missing a beat.
Brunello Cuccinelli
J.M. Weston Jodhpur Boot
The J.M. Weston Jodhpur is what happens when French finesse meets equestrian edge. Crafted in Limoges (yes, that porcelain place), this pair of boots features attractive vegetable-tanned leather, shaped on wooden lasts for a sharp silhouette. The ankle strap isn’t just for show—it’s a nod to the equestrian origins of the Jodhpur style.
J.M. Weston
Manolo Blahnik Sapele Boots
These Italian-made marvels marry hiking boot grit with Wall Street polish. A lugged rubber sole, no-nonsense lacing system, and strategic broguing create a boot that is at home scaling corporate ladders or actual mountains with equal aplomb.
Manolo
Red Wing Shoes Classic Moc Boots
Red Wing’s Classic Moc toe boot is the Clint Eastwood of men’s footwear: rugged, enduring and quintessentially American. Its Puritan triple-stitching and Goodyear welt construction ensure longevity that’ll outlast your next three cars. Yes, there’s a break-in period—consider it a boot boot camp—but once you’ve earned your stripes, you’ll have footwear that transitions from coffee shop to job site, no questions asked.
Red Wing
John Lobb Alder Leather Boots
John Lobb’s Alder boots, inspired by the daring spirit of 1940s ski escapades, are engineered to conquer any terrain—a more rugged take on the classic Balmoral dress boot. The British brand’s signature palladium lace hooks infuse a touch of elegance into their sturdy build. With Goodyear-welted construction, notched storm welts and rubberized soles, they ensure lasting comfort and durability. Ideal for weekend explorations or urban adventure.
John Lobb
Todd Snyder Nomad Suede Chelsea Boot
The Chelsea boot, a timeless classic tracing its lineage back to Victorian elegance, found its fame with England’s 1950s “Chelsea Set.” Todd Snyder’s Italian rendition elevates this icon with sumptuous suede uppers and supple crepe soles, harmonized with the quintessential elastic side panels for a flawless fit. Whether paired with denim or wool trousers, these boots deftly strike a chord between heritage and contemporary.
Todd Snyder
Blundstone Chelsea Boots
Blundstones are a versatile powerhouse, seamlessly transitioning from the rugged wilderness of Tasmania to the avenues of Manhattan. The boot brand’s utilitarian 1615 model, in particular, encases your feet in water-resistant waxed suede. Equipped with Blundstone’s SPS Max Comfort system and a robust outsole, the slip-on shoes ensure unmatched comfort and steadfast grip.
Blundstone
Le Majordome M59 Galosh Boot
Swiss shoemaker Le Majordome beefs up its Goodyear welted derby design with a three-loop hiking lacing and dual hook system. Think of it as a handshake between high society and the wild outdoors: The texture play of the rugged Spanish light brown cowhide practically begs for adventure, while the cream-colored winter sole gives visual contrast and durability. Want to up the ante? Swing by the New York City boutique and put your own custom spin on the boot’s look.
Le Majordome
Ralph Lauren Leather Boots
Old-world craftsmanship meets street-smart style with Ralph Lauren leather lace-up boots. The combat boot-inspired cap toe shoe is stitched together in a legacy shoe factory in England, with burnished leather sourced from a famous Chicago tannery, meaning these brogues get more attractive with every step.
Ralph Lauren
Celine Homme Margaret Chelsea Boots
These Celine Chelsea boots are a fusion of old-school cool and trending modern mojo. The sleek black leather upper nods to tradition, while the chunky lug sole plants a flag firmly in contemporary territory. Easy-on elasticated sides meet pull tabs in a boot that’s both practical and philosophical. It’s footwear for those who appreciate paradox—and punctuality.
Céline
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