The Best Men's Fall Boots: Chelsea, Chukka, Service, Western and Hiking Pairs

The men's fall boots worth owning come down to three pairs: a slim Chelsea boot in dark suede or calf for tailoring, a chukka or desert boot for weekends, and a lace-up on a rubber sole for the wet weeks. Add a dress boot if you wear suits often, and a Western or hiking-inspired pair only if your life has room for it. This guide takes each style the way a stylist would: how it is built, how it should fit, which trousers it suits, and whether to choose leather or suede when the forecast turns. The edit covers designer boots for men in eight styles, from houses including Saint Laurent, John Lobb, Brunello Cucinelli, Tom Ford and Tod's. Shearling-lined and snow boots live in our men's winter boots guide.

Men's fall boots at a glance

Fall asks less of a boot than January does. You are dealing with rain, wet leaves and mild afternoons rather than ice and deep cold, which is why soft suede, slim leather soles and lighter shapes still earn their place. The table runs from the most formal style to the most casual.

Chelsea boots for men: slim for tailoring, sturdy for weekends

The elastic-sided boot has two personalities, and the sole tells you which one you are looking at. The slim version sits on a leather sole with a short stacked heel and an elongated toe, and it is the smartest boot most men will ever need: Saint Laurent's Aurelien, which the listing describes as Blake rapid-stitched on a leather sole with a one-inch heel, disappears under a suit trouser the way an Oxford does. Tom Ford's Elkan, in burnished leather, does the same with a little more shine. The second version sits on rubber: a lugged sole on Bottega Veneta's Ben, a thick, rounded one on Prada's brushed-leather pair, and it belongs with denim and weekend layers.

Toe shape decides formality more than color does. An almond or elongated toe reads like a dress shoe; a round toe on a thick sole reads like workwear. Stand up in them before you decide: the elastic should lie flat against the ankle bone, with no puckering in the leather on either side of it. A Chelsea whose top line gapes at the back of the ankle will let the trouser hem catch inside it all day.

• Black calf Chelsea boots, a navy birdseye suit, a pale blue poplin shirt and a charcoal overcoat.
• Dark brown burnished Chelsea boots, taupe cavalry twill trousers, a cream roll-neck and an olive suede blouson.
• Black brushed-leather Chelsea boots on a chunky sole, mid-blue straight jeans, a gray sweatshirt and a black leather jacket.

Suede Chelsea boots for men

Suede looks warmer than calf, and in a dark shade it is dressier than its weekend reputation suggests. Saint Laurent's Wyatt in dark chocolate suede, with a stacked heel of about an inch and a half and a leather sole, is the sharp one. John Lobb's Lawry is the long-term buy: the listing describes it as Goodyear-welted, on vegetable-tanned soles with rubber tips for grip. Tod's sets its Winter Gommino on the house's pebbled rubber, which makes it the suede Chelsea for a city that is wet more often than it is dry.

Choose the sole before the color. A suede Chelsea on a leather sole is a dry-day boot, however well you protect the upper; the same boot on rubber can go out under a gray sky.

• Dark chocolate suede Chelsea boots, ecru jeans, a cream cable knit and an olive field jacket.
• Hazelnut suede Chelsea boots, gray flannel trousers, a white Oxford shirt and a burgundy cardigan.
• Black suede Chelsea boots, indigo jeans with one small turn-up, a white T-shirt and a navy cashmere cardigan.

Chukka boots and desert boots

A chukka is an ankle-high boot with two or three pairs of eyelets. The desert boot is its best-known form, and its origin is documented: the Alfred Gillett Trust, whose collections include the Clarks business archives, records that Nathan Clark designed it in 1949, modeled on a style made in the bazaars of Cairo, and that a year later, at the Chicago Shoe Fair, Clark turned his stand into a desert oasis, where the boot was presented on a silk pillow. Most desert boots today are soft suede on a thin rubber sole, which makes them the lightest and most casual boots in this guide.

The chukka family has since been dressed up. John Lobb makes a Goodyear-welted nubuck chukka on a rubber lug sole, and its Field desert boot swaps suede for full-grain leather with what the listing calls a notched storm welt. Ferragamo's Settimo, in smooth leather with an almond toe, is the chukka that will pass under a flannel suit.

Two judgements to make before you buy. First, a suede desert boot on a thin sole is not a rain boot. For wet weeks, choose a chukka on a lug sole, like John Lobb's nubuck Field, or protect the suede before you wear it (the care notes below explain how). Second, buy the shade your trousers need. Dark brown, charcoal and navy suede cover most of fall; sand and beige belong to the first mild weeks of the season and look best with lighter trousers.

• Navy suede chukkas, light-gray wool trousers, a white Oxford shirt and a navy quilted gilet.
• Tobacco suede desert boots, olive chinos, a cream Shetland crewneck and a chocolate suede overshirt.
• Charcoal suede desert boots, mid-blue jeans, a gray marl sweatshirt and a black wool overshirt.

Lace-up boots for men: service boots and derby boots

Most lace-up boots in a man's wardrobe are derby boots, and the lacing explains why they are so easy to wear. As the Northampton shoemaker Cheaney explains, a derby's eyelet facings are sewn on top of the vamp, so the lacing is open and the facings can be loosened a long way; an Oxford's are stitched under the vamp, which closes the lacing and holds the fit snug across the instep. So if your instep is high, or you like a heavier sock in fall, derby lacing is the one to look for.

The service boot is the plainer lace-up with a military look: a plain or capped toe, a sturdy sole and a shaft that clears the ankle. Brunello Cucinelli's cap-toe suede derby boots are exactly that, and their listing describes them as grounded in military styling. John Lobb's Alder goes into the house archive instead: the listing says it is inspired by a 1940s ski style John Lobb has preserved, finished with a bellows tongue and a Goodyear-welted rubber sole. The sole tells you where a lace-up belongs. A slim leather or leather-and-rubber sole keeps it in town; a commando sole sends it to the country.

A service boot should rise just above the ankle bone, high enough for a trouser to fall cleanly over the shaft instead of catching on the top eyelet.

• Gray suede cap-toe service boots, raw indigo jeans with a small turn-up, a white Oxford shirt and a navy chore jacket.
• Chestnut leather service boots, mid-gray flannel trousers, a cream crewneck and an olive waxed jacket.
• Black leather derby boots, charcoal corduroy trousers, a burgundy lambswool crewneck and a black wool overcoat.

The dress boot: side-zip, jodhpur and monk-strap boots

A dress boot is the one boot that can replace an Oxford with a suit, and four details make it one: a slim sole, usually leather; a shaft that hugs the ankle so it vanishes under the trouser; a heel of roughly an inch to an inch and a half; and a closure that adds no bulk. The side-zip boot is the cleanest version. Saint Laurent's Aurelien zip boot sits on a Cuban heel of 3 cm (about 1.2 inches), according to the listing; Tom Ford's Elkan comes in burnished black leather; Loewe's Bobine uses two side zips. John Lobb's Regi, from what the house calls its Officer line, borrows from English riding boots.

The jodhpur boot wraps a strap around the ankle and buckles it at the side, as on The Row's Nobilis and Tom Ford's Hainaut. The monk-strap boot puts the buckles across the instep instead; John Lobb's Alliance is a double monk on a Goodyear-welted rubber sole. Whichever you choose, hem your suit trousers while wearing the boots. A heel of even an inch lifts the hem, and a trouser cut for flat shoes will show a strip of sock when you sit.

• Black side-zip boots, a navy worsted suit, a white shirt and a black knitted silk tie.
• Bark-brown kidskin boots, a mid-gray flannel suit and a cream roll-neck for a dinner where a tie would be too much.
• Black double monk-strap boots, a charcoal chalk-stripe suit, a pale gray shirt and a burgundy tie.

Our men's date night outfits show how far a dress boot can carry a jacket and trousers.

Western boots for men

Western boots follow a vocabulary of heels and toes, and the Texas bootmaker Lucchese, in business since 1883, sets it out plainly in its guide to toe and heel options: a cowboy heel stands 1¾ inches, a walking heel 1½ inches and a roper heel 1 inch. The snip toe, Lucchese says, was originally made for getting in and out of a stirrup, while the rounded roper toe is the one most like an ordinary shoe. Read a fashion listing with that chart beside you. Christian Louboutin's Santiagus sits on a 1.77-inch heel, cowboy height, with a metal toe guard. Jil Sander's Bruce, a tall suede pull-on, sits on about an inch, roper height. Versace's Tigre is a low-cut Texan boot; Maison Margiela's version removes the heel altogether.

For a first pair, choose a roper or walking heel, a round or medium toe and a shaft that stops below the calf. That combination walks comfortably and sits neatly under straight jeans. A snip toe on a cowboy heel is a statement boot, best worn with plain, dark denim and little else competing for attention. Wear the jeans over the shaft, never tucked in. Few luxury houses make men's Western boots, so the edit below is short.

• Black Western boots, mid-blue straight jeans worn over the shaft, a white T-shirt and a black suede trucker jacket.
• Walnut suede Western boots, ecru jeans, a cream work shirt and an olive corduroy jacket.

Lug-sole boots for rain and wet leaves

A deep rubber lug sole is the most practical answer to a wet fall, and the luxury versions now come in every shape: The Row's Moto with a side zip, Saint Laurent's Joe as a Chelsea, Louboutin's Trapman as a lace-up with a knitted collar, and John Lobb's Peak, which the listing says draws on Scandinavian hunting boots. The playful one is the Moncler collaboration with Clarks Originals, which puts the Clarks Wallabee on a Vibram Megagrip tread, a neat echo of the Clarks story above.

The mistake with lug soles is proportion. A heavy sole needs a heavier trouser: straight or relaxed jeans in a substantial denim, cords, cargo trousers or wool with some width at the hem. Over a slim, cropped trouser, a chunky boot looks borrowed. Brush the lugs after a wet walk, too: leaves and grit pack into the tread, and a clogged tread grips less.

• Black lug-sole Chelsea boots, dark indigo straight jeans, a charcoal hoodie and a black technical parka.
• Espresso suede lug boots, olive cargo trousers, a cream sweatshirt and an olive field jacket.

Hiking-inspired boots

These borrow the hardware of mountain boots (D-rings, speed hooks, a padded collar and a commando or lug sole) for weekends, country houses and travel. Brunello Cucinelli builds them in what the listing calls water-resistant waxed suede, on commando soles; Moncler's Peak City, in nubuck and suede, nods to the brand's mountaineering past; and Christian Louboutin's Armandine College mixes leather and suede over the house's red rubber sole.

Keep hikers away from tailoring and lace them all the way up; a hiking boot worn half-laced looks sloppy rather than relaxed. Two-tone and bright laces (Prada's yellow, Brunello Cucinelli's contrast tan) are part of the appeal, so let the rest of the outfit stay plain.

• Brown leather hiking boots, gray wool trousers, a burgundy fisherman knit and an olive waxed jacket.
• Charcoal waxed-suede hiking boots, mid-blue jeans, a gray fleece and a navy quilted jacket.
• Camel nubuck mountain boots, stone chinos, a cream rollneck and an olive field jacket.

How to wear boots with jeans, chinos and tailoring

Vêtir's stylists follow two color habits that shape every outfit above. They keep brown, tan and camel boots away from blue denim and navy, and they keep black away from brown. In practice, that means the color of your trousers picks the boot:

Then get the hem right. With jeans, a straight leg should fall over the boot with one soft break; a small single turn-up shows off a lace-up's shaft, while skinny jeans stacked on top of a boot look dated. With tailoring, ask for little or no break and keep the boot slim and leather-soled. Socks should continue the trouser, not the boot, so the leg reads as one line when you sit. For the layers above the boots, see our guides to men's fall jackets and the men's fall wardrobe; for the dinner on Thursday, November 26, see our men's Thanksgiving outfits.

Suede or leather: men's boots in fall rain

For a week with an uncertain forecast, smooth leather is the safer choice: it sheds a shower and wipes clean, and Lucchese's care guide reduces its upkeep to clean, condition, polish and protect. Suede asks for more planning but less dread than its reputation suggests:

• Before the first wear, treat suede with a non-silicone water and stain protector, as Lucchese recommends.
• If it gets wet, blot the excess with a clean towel, let it dry naturally with boot trees inside, and keep it away from radiators and other direct heat. Brush off dried mud once the boot is dry.
• Some suedes arrive protected. The Leeds tannery C.F. Stead makes its Repello calf suede for men's dress and casual shoes, treats it with Scotchgard during tanning for stain resistance, and says the proofing lasts the life of the footwear. When a listing names the leather, it is telling you something useful.
• Waxed and oiled finishes trade a little softness for water resistance, which is why Brunello Cucinelli's waxed-suede hiker is a better wet-day boot than an unwaxed suede one.

The sole matters as much as the upper. A smooth leather sole slips on wet leaves, so a leather-soled boot needs help in the rain: rubber tips on the sole, as on John Lobb's Lawry, or a studded rubber sole. Dainite is the studded sole to look for in a listing. The English shoemaker Barker writes that it was originally designed to grip in all conditions without attracting or storing dirt, and that Northampton makers including Crockett & Jones, Church's and Cheaney use it. It is still made in Market Harborough, England, by the Harboro Rubber Company, which has been making rubber moldings since 1894. For real downpours, choose a commando or lug sole and a smooth or waxed upper, and save soft suede on thin soles for dry days. Cedar boot trees, which Lucchese suggests for holding shape and drawing out moisture, are the cheapest insurance a good pair can have.

How men's boots should fit, style by style

Lucchese offers two fitting tips that apply well beyond Western boots: do not press the toe with your hand to judge the fit, as you would with a shoe, because with a boot it is not a true test and can damage the leather; and if one foot is slightly larger than the other, buy the size that fits the larger one. After that, each style has its own test.

• Chelsea boots have no laces to let out, so a boot that is tight over the instep in the shop will stay tight. Walk a few steps: the heel should lift only slightly, and the top line should sit close to the ankle without biting when you flex.
• Side-zip and jodhpur boots should zip or buckle without strain over the instep. If you have to force the zip on day one, the boot is too narrow.
• Chukkas and desert boots in soft suede give a little as you wear them in, so choose snug over roomy.
• Derby and service boots forgive the most, because open lacing lets you loosen or tighten across the instep. A useful check in the fitting room: laced snugly, the facings of a new pair should sit a little apart and roughly parallel. If they already meet, there is more room over your instep than you need; if they splay into a wide V, there is too little.
• Hiking-inspired boots should leave room for a heavier sock. Read the listing's fit note: Manolo Blahnik's Janka, for one, is described as running large.

Check the size system before you compare, because it follows the retailer as much as the house. In this edit every John Lobb pair is listed in UK sizes and every Versace pair in European ones, but Loewe's boots appear in both European and US sizes, and a bare 9 can mean either side of the Atlantic. Open the size guide on the listing before you order. Our winter boots guide has a conversion chart from Crockett & Jones.

Buy once, or enjoy for a season

Three pairs earn their price over many years: a dark brown or chocolate suede Chelsea or chukka, a black calf Chelsea or side-zip boot, and a welted lace-up. Welting matters because it allows resoling; John Lobb's listings describe Goodyear welting for a lifetime of wear, and a Norwegian welt on the Peak. Buy those in the most classic shape you can live with.

Then there are the one-season pleasures, which are fine as long as you buy them knowing it: Prada's hikers with yellow laces, Louboutin's metal-toed Santiagus, Margiela's heel-less Western boot, Burberry's check-collared Durham. Loud boots date faster than plain ones.

The common mistakes: a chunky lug sole bought for a wardrobe of slim trousers; a suede-only rotation in a city where it rains every week; a heeled dress boot worn with trousers hemmed for flat shoes; skipping the protector on new suede; and hiking boots worn with a suit. If you already own a few pairs, our AI stylist can check them against the trousers in your digitized closet and tell you which gap to fill first. For loafers, which handle many of the same occasions, see our guide to the best loafers for men.

How we chose

We sorted boots by how they are made and worn rather than by brand: sole and construction, lining, toe shape, heel height and closure, each read from the listing. Every boot's photograph was checked against its stated color and material; two pairs sold as smooth-leather Chelsea boots turned out to be suede in their pictures, and one desert boot showed a shearling lining its listing never mentioned, so all three were left out. The edit spans 23 luxury houses, from under $1,000 to about $3,000; most pairs had five or more sizes when we checked, and where a category is genuinely small, as with men's Western boots, we say so. Browse more Chelsea boots, ankle boots, Western boots and combat boots in the men's shop.

Frequently asked questions

What are the best boots for men in fall?

Start with a dark suede Chelsea or chukka, a black calf Chelsea or side-zip boot for tailoring, and a lace-up on a rubber sole for rainy weeks. A Western or hiking-inspired pair is an addition, not a foundation.

What is the difference between a chukka and a desert boot?

A chukka is any ankle-high boot with two or three pairs of eyelets. A desert boot is a particular chukka: the soft, usually suede, rubber-soled version descended from the boot Nathan Clark designed for Clarks in 1949. Every desert boot is a chukka, but a welted calf chukka is not a desert boot.

What color boots should men wear with jeans?

With blue jeans, Vêtir's stylists choose black, charcoal, gray or navy boots. Brown and tan boots go with ecru, white or gray jeans, and with stone, olive or cream chinos.

Can you wear suede boots in the rain?

Yes, with preparation. Treat new suede with a water and stain protector, choose a rubber sole, and blot and air-dry the boots after a wet day. Pre-proofed or waxed suedes cope best; soft suede on a leather sole is a dry-day boot.

Are Chelsea boots business casual?

Yes. A slim Chelsea in calf or dark suede on a leather or thin rubber sole works with chinos, flannel trousers and a blazer, and a black calf pair works with a suit. Chunky lug-soled Chelsea boots are for the weekend.

Can you wear lug-sole boots with chinos?

Yes, if the chinos have some weight and a straight leg. Heavy twill with a hem that rests on the boot looks deliberate; thin, slim chinos over a thick sole look unbalanced.

Keep reading

• The best men's winter boots
• Men's fall outfits and a 12-piece capsule
• The best loafers for men
• The best men's winter coats
• The best boots for fall, for women