CHELSEAS, CHUKKAS & MORE

The 50 Best Boots for Men


April 1, 2020 Style By Photo by Henry Phillips
Purchasing products through our links may earn us a portion of the sale, which supports our editorial team’s mission. Learn more here.

Last Updated April 2020. This definitive guide to the best boots for men covers ten categories, including work boots, Chelseas, chukkas and more.

Boots always seem to get more done than shoes. While shoes are busy arguing semantics in a boardroom, boots are out in the garage actually doing work. Shoes spend their weekend shanking golf balls while boots are going over, around and through every surface on Earth. Boots have long belonged to the movers and shakers of history, and dammit if they’re not going to keep going. Here are the 50 best pairs you can buy right now.

Chelsea Boots

Chelsea boots began life in England in the mid-19th century and didn’t stray far from home until recently. The elasticized wonders were a staple of the mid-’60s mod scene and protected the feet of seemingly every British invader from John to Ringo. Recently they’ve seen a revival on many of menswear’s best dressed. The silhouette is very slim and features elastic side panels and heel pull-tabs.

Blundstone 550 Boots

Technically part of the Australian bush boot lineage of boots, Blundstone’s 550 boot is one of the best values you can get. It’s a top choice for people in every industry thanks to the tough leather upper, shock-absorption and classic design.

R.M. Williams Craftsman Boots

R.M. Williams’ Craftsman Boot is its best-selling boot, braving the Australian outback on the feet of its hardest-working cowboys. The single, one-piece leather upper is supple yet durable and the Goodyear-welted construction extends the life of the boot several factors over. If it’s tough enough for Aussie cowboys, it’s tough enough for you.

Taylor Stitch Ranch Boots

The Ranch Boot from Taylor Stitch is handcrafted in Léon, Mexico, a town known as the shoemaking capital of the world. With a saddle tan leather upper, sheepskin leather lining and full leather insole and outsole, it’ll get more comfortable with every wear. And, the Goodyear stormwelt means it’ll keep out moisture and take several resoles.

Common Projects Chelsea Boots

An instant classic since it was introduced into the lineup of luxury footwear brand Common Projects, this Chelsea boot features supple suede and a comfortable crepe rubber sole. Kanye’s been known to rock this version, but it’s not limited to hip-hop royalty.

Prada Novo Chelsea Boots

Prada’s Novo Chelsea boot offers a designer take on the more rough and ready Chelsea boots like the Blundstone 550s, combining supple calfskin with neoprene and elastic gussets atop a chunky lug sole. The Italian-made boot has been the favorite of the fashion elite.

Ankle Boots

Ankle boots might be the coolest footwear ever made — which makes them that much more difficult to pull off than their closest cousins, the Chelsea boot. They’ve graced the feet of rock stars and, in doing so, complemented the tightest pants mankind has had to offer for decades. The silhouette is similar to the Chelsea boot, but the Ankle boot utilizes zippers or straps, instead of elastic panels, to ensure a secure fit around the ankle.

Thursday Rogue Boots

Thursday Boots offers some of the best value for money with quality details like Goodyear-welt construction cork beds for comfort and weather-resistant leather uppers. Its Rogue Boot is perhaps the brand’s most stylish boot thanks to the Jodhpur design and Cuban heel.

Two24 by Ariat Jefferson Boots

Featuring quality British suede used by the likes of Clarks and Viberg, Two24 by Ariat’s Jefferson boot is a moto-style ankle boot that’ll look better with some miles on it. The side zip design gives this pair a slick edge to its rugged looks and the fact that it’s resolable makes the price tag even sweeter than it already is.

Frye Chris Inside Zip Boots

Like the Two24 by Ariat’s Jefferson boot, Frye’s Chris Boot features a texturally satisfying suede coupled with a side zip entry. But, the hidden zip gives Frye’s version a cleaner, more minimal look.

Lucchese Jonah Boots

Premiere cowboy bootmaker Lucchese’s Jonah Boot serves up an elegant zip-up that riffs off of both roper and equestrian-style designs. The stacked leather heel and Goodyear-welted design are quality markers, par for the course fo the multi-generational brand, and the calfskin uppers are expertly burnished for more character.

Saint Laurent Wyatt 30 Jodhpur Boots

Boots don’t get much sexier than Saint Laurent’s Wyatt 30 Jodhpur Boot. The brand’s slick designs and rock star appeal come through with this strapping pair which features a gorgeous suede upper, and full-leather soles.

Wingtip Boots

The wingtip, whose brogued details bring a touch of formal embellishment to casual footwear, is dressed up enough to be worn with a suit and laid back enough to end up under denim or a pair of cords. But they’re not a mullet shoe: they’ve been around long enough to look equally good in either context.

Velasca Sciostree Boots

Milan-based brand Velasca has been noted by footwear enthusiasts for its surprising price-to-quality ratio and its entry into the wingtip boot world is of particular appeal. The pebble grain kudu leather upper, classic wingtip brogue embellishments and tough Vibram lug sole make this boot worthy of the English countryside.

Grenson Fred Leather Brogue Boots

These English brogue boots are built to take on the countryside with a water-resistant storm welt and chunky rubber lug sole. The full-grain leather upper is subtly burnished for a classy look that pairs well with a suit or jeans.

Rancourt Brighton Boot

Made in the USA, Rancourt’s Brighton Boot features a handsome cap-toe brogue design in a French calfskin upper. The Blake-stitch construction makes it flexible and resolable while the lug sole prepares the boot for any situation.

Tricker’s x Division Road Stow Boots

One of the most popular shoes from Northampton, England-based brand Tricker’s is certainly its Stow Boot. It’s a quality boot with details like a wooden shank and cork footbed for comfort and support, as well as a Goodyear-welt construction. It comes in many leathers, but this one is a standout thanks to its reverse kudu suede upper.

Thom Browne Classic Wing Tip Boots

These wingtip boots from famed American designer Thom Browne are a staple in his eponymous collection and feature a beautiful pebble grain leather upper rendered in a shortwing semi-brogue design atop a rubber sole. The red-white-and-blue stripe motif is a calling card for the luxury brand and is featured here in a grosgrain heel tab.

We Cut 5 Great Boots in Half to See What Makes a Quality Pair

Often, it’s difficult to picture how a boot is actually put together, where the stitches go and what you’re actually standing on. So we sourced prime examples of each type of boot construction — Cemented, Blake/McKay, True Moccasin, Goodyear Welt and Stitchdown — from some of the top brands in the industry and cut them in half. Read the Story

Chukka Boots

About as casual as all-leather boots get, the chukka (or desert) boot was first worn by British soldiers in Africa during World War II. Afterward, they made their way across the Atlantic, becoming a casual staple for the second half of the 20th century and still gracing the feet of stylish men in the cooler months. Clarks made the originals, but upmarket offerings only improved on the formula. They lace up just above the ankle and traditionally feature a soft crepe sole.

Clarks Desert Boots

The definitive desert boot is still made using supple and rugged English suede from the world-famous CF Stead leather tannery. Its crepe rubber sole gives superior cushioning and traction, too.

J.Crew 1990 MacAllister Boots

These made-in-Italy desert boots offer a slightly beefier construction than Clarks’ iconic version and feature premium Italian suede uppers as well as natural crepe rubber soles. The profile of J.Crew’s version is a tad more refined that makes this one well-suited for dressing up.

Wild Bunch MST14 Vibram Sole Work Boots

Forgoing the usual crepe sole, Wild Bunch’s take on the chukka opts for a platform Vibram sole instead. The effect gives the shoe a workwear vibe, along with the contrasting welt.

Sanders Hi-Top Chukka Boots

One of the most popular models for English shoemaker Sanders is its Hi-Top Chukka, which nearly blends the profile of a traditional chukka with the sole of a sneaker. The crepe sole wraps around the upper similar to a sneaker while providing superior grip and comfort.

To Boot Riverside Chukka Boots

To Boot’s Italian-made chukka comes with a superior suede upper with a sleek silhouette. The combination of the blind eyelets, contrast leather storm welt and the natural crepe rubber make its entry a refined-yet-rugged take on the desert boot.

Hiking Boots

For the purposes of this guide, we’ve kept a respectful distance from the more technical versions of this style, but the best pairs of old-school hiking boots boast the same alpine prowess that made them popular in the first place. Sturdy soles, heel support and lace-to-toe closures mean these boots are as hardworking as they are good-looking.

Fracap M120 Ripple Sole Scarponcino Boots

Fracap’s Scarponcino Boot is made for the Italian alps and looks completely intimidating thanks to the chunky ripple sole. Fully-leather lined, the badass boot features stitchdown construction for long-lasting wear.

Danner Light Revival Boots

Combining premium full-grain leather uppers with a lightweight 1000 denier nylon, Danner’s classic Light Revival boot is lighter than most hiking boots without sacrificing performance. Its Gore-tex lining keeps water out while the Vibram Kletterlift sole handles all kinds of tough terrain.

Paraboot Avoriaz Boots

The French-made Avoriaz boot is unique because its soles are all made in-house by Paraboot. The vertical production allows the brand greater quality control which is evident here. Classic hiker styling with a padded collar, leather lining, speed hooks and chunky contrast laces bring everything together.

Viberg Hiker Natural Chromexcel Boots

Canada-based brand Viberg’s Hiker takes after the iconic designs of Danner as the two founders have had a friendly history together. This boot features a gorgeous natural Chromexcel leather that will patina and darken with wear, charming red shoelaces, leather insoles and midsole, and a commando leather sole.

Feit Metal Military Hiker Boots

Feit’s Metal Military Hiker uses painstakingly hand-stitched Goodyear-welt construction with a vegetable-tanned leather upper. The leather accents give its hiker a futuristic punk edge while the wrap-around laces provide extra support.

Hunting Boots

For actual hunting, you may want something more technically advanced, but the hunting boot is a staple in the Northeast and has ensconced the feet of everyone from frat boys to Nobel prize winners. The traditional style features a hand-sewn moc-toe, a lace-up closure and a durable grippy outsole.

L.L.Bean Boots

L.L.Bean is known most for its famous Bean Boot, the original ‘duck boot.’ First introduced in 1912, the waterproof boot combines a rubber outsole and quarters with a full-grain leather upper for maximum waterproofness and comfort.

Rancourt Sherman Boots

Rancourt’s Sherman Boot is not only appealing for its brass eyelets, natural lactae hevea crepe soles and true-moccasin construction. It’s also a looker thanks to the shrunken bison leather upper which gives the boot a grainy character that stands out amongst the smooth-leather options on the market.

Maine Mountain Moccasin Scout Boots

Maine Mountain Moccasin’s Scout Boot is its most popular, for good reason. The true-moccasin construction gives it a classic look and the full-leather double midsole paired with Blake construction mean it’ll be a tough pair to wear out.

Russell Moccasin America Bison 5.5 “PH” Boots

Russell Moccasin’s hunting boot is unique in that it combines a handsome bison leather with tough cotton duck, shedding some weight in the process while providing comfort and durability. The brand offers it in a variety of options with soles of your choice.

Yuketen Maine Guide DB Boots

These boots are some of the best that Yuketen has to offer, deftly mixing smooth leather with flesh-out suede. It features genuine double-lined moccasin construction attached to a thick Vibram Christy sole, combining waterproofness with supreme durability.

How to Break in a Pair of Boots the Right Way

When you invest in a new pair of well-made boots, don’t expect to lace them up and take on the world in the same day. Thick leather uppers and solid leather midsoles take a while to break in and rub and squeeze your feet, leading to painful blisters if you’re unprepared. While the sturdiness and durability of boots vary widely from brand to brand, there are a few universal tips for breaking in a new pair, regardless of brand. Read the Story

Work Boots

Strong, long-lasting and just stylish enough to stay on your feet for most of the colder months: that’s all a work boot really needs to be. Little wonder that the design was more or less perfected half a century ago. The no-frills lace-up style protects the lower legs and feet and usually features a durable lug sole.

Red Wing Iron Ranger Boots

Red Wing is known for its long-lasting work boots and its Iron Ranger Boot is iconic.
It features a protective cap toe, cork misdole for comfort, speed hooks and Goodyear-welt construction. The tough pull-up leather is tanned by the brand’s own tannery and certainly requires a break-in, but many fans are adamant that it’s well worth it.

Wolverine 1000 Mile Boots

Wolverine makes a bold claim with its 1000 Mile Boot. But the full-grain Chromexcel leather upper, paired with a full-leather sole back it up. It’s handsome enough to polish up and pair with some dress trousers, but not too precious to take a hard day’s work.

Wesco Jobmaster Boots

Wesco’s Jobmaster gets the job done with full-grain leather uppers and a beefy Vibram lug sole, standing tall at 10 inches. It features nearly-indestructible construction with full-leather insoles and midsoles and brass eyelets that get better with age.

Nicks Handmade Boots Robert Boots

Nick’s Handmade Boots is another one of the famed bootmakers out of the Northwest and its Robert boot is as pretty as it is durable. This pair features stitchdown construction with a leather midsole, Vibram outsole and a sculpted stacked leather heel, as well as brass eyelets and leather laces.

White’s Farmer/Rancher Boots

White’s Farmer/Rancher boot is a classic workwear design that both fashion enthusiasts and the workforce prize. The Cuban heel complements the silhouette of the boot while the stitchdown construction, leather midsole and shank ensure its quality.

Trench Boots

Worn since World War I, the trench boot (sometimes called an army or officer boot) is a handsome staple that’s shaken its military roots and manages to look a bit more cleaned up these days than it did stomping into Flanders. Similar to the work boot, this silhouette has a lower profile that is easier to incorporate into a variety of wardrobes.

Grant Stone Diesel Boots

There aren’t many brands that offer as much for your dollar as Grant Stone and its Diesel boot gets great mileage. The full-grain leather upper, the cork filling, steel shank and Goodyear-welted construction are all details you’d normally find on pricier pairs.

Oak Street Bootmakers Trench Boots

Oak Street Bootmakers built its brand on its WWII-inspired trench boot and has remained a tentpole for the brand to this day. This pair is made in the USA and features Chromexcel leather uppers from Chicago’s Horween Leather Co, brass eyelets, rawhide laces and a leather sole.

Viberg Service Boots

Viberg’s Service Boot differs from most other trench boots due to its signature stitchdown construction. The silhouette is as sleek as it is tough and the Dainite rubber soles make it a surefooted boot in times of rain and snow.

Crockett & Jones Coniston Boots

Premier English shoemaker Crockett & Jones are lauded for its heritage and quality. Its Conston boot is one of its more rugged offerings, featuring a beautiful scotch grain leather upper, storm welt and Dainite soles, but is equally dressy thanks to its cap toe and blind eyelets.

John Lofgren M-43 Service Boots

John Lofgren is well-versed and well-respected in the boot world and the M-43 Service Boots are as close as you can get to a real deal vintage pair of WWII service boots. These are built in Japan around the historically accurate Munson last and feature a natural Chromexcel roughout upper with an unstructured toe, all attached via Goodyear welt to a Vibram 705 sole and Vibram 700 heel.

Cowboy Boots

Like many Americana wardrobe staples, cowboy boots are rooted in function. Pull them on, wear them hard and use them for years. There are two mains styles: traditional cowboy boots that feature a riding heel (taller and angled) and roper boots that have a shorter heel, designed to handle a day of walking. The pointed toe and tall shaft make this boot instantly recognizable.

Tecovas Johnny Boots

Direct-to-consumer brand Tecovas has been on the radar of many a cowboy boot fan thanks to its balance of quality details and affordable prices. Its Johnny boot comes with a water-resistant suede, a leather stacked heel, and 3/4 goodyear welt construction.

Red Wing Pecos Boots

The Pecos boot from Red Wing has been around since the 1930s and offers a toned-down version of the traditional cowboy boot by forgoing the decorative stitching and exaggerated heel. The silhouette leans more into the work boot world and the durable Hawthorne Muleskinner leather will gain more satisfying texture with wear.

Rios of Mercedes Sand Elk Bottom Cowboy Boots

Rios of Mercedes has been crafting cowboy boots for over 160 years and its Sand Elk Bottom is a favorite. It features elegant french binding, western stitching at the shaft, a leather-rubber combination sole and a Cuban heel.

Lucchese Tanner Boots

Lucchese multi-generational boot tradition is revered the world over and its roper-style Tanner Boot is a standout. Featuring a premium goat leather upper that’s full of patina and character off the bat, the Tanner is a shorter cowboy boot that’s built in Texas using a resolable welted construction

Heritage Boot Co. Ranch Hand Boots

Heritage Boot Co. has a vast array of cowboy offerings from the basic entry-level styles to boots with the exotic leather and hand-tooled designs. The Ranch Hand features a luscious brown suede for the upper which is then decorated with western stitching. The combination of the Cuban heel and the chiseled toe make it one of the most covetable boots on this list.

Engineer Boots

The original engineer boots were designed to protect the feet of men who fed coals into steam engines. It melded the tall pull-on style of horse riding boots with the supportive arch and sole of a work boot. A buckled ankle strap distinguishes this style from other pull-on boots.

Red Wing Engineer Boots

It’s hard to resist multiple entries from Red Wing on an all-encompassing boot list, especially with the brand’s signature Engineer Boot. It features premium Goodyear welt construction, a cork-filled insole for comfort and a price that’s hard to beat.

White’s Nomad Boots

The burly Nomad Boot from White’s is built as tough as they come with a water-resistant leather upper, full-leather midsole and shank, mini Vibram sole and hardy stitchdown construction.

Viberg Engineer Boots

Viberg’s entry into the engineer boot category is notable for its natural Chromexcel leather that ages quickly and is easier to break in. It pairs well with the brass hardware and, of course, is backed by Viberg’s penchant for quality construction.

The Flat Head Goodyear Welted Engineer Boots

Straight from Japan, these boots from The Flat Head are some of the rarest on the market. Made in small batches, the boots feature natural Chromexcel pull-up leather, storm welt construction, steel shanks and custom-made brass hardware.

Wesco x Standard & Strange Knuckle Dragger Engineer Boots

In tandem with Oakland-based retailer Standard & Strange, the Wesco Knuckle Dragger features an amazing olive waxed flesh leather upper that ages into an exotic avocado green with wear. All-leather construction at the midsole and insole as well as the lining make it comfortable to slip on and tough to wear out.

3 Northwestern Boot Makers You Should Know

While they’re perhaps not as well known as brands in other regions, the original boot companies of the Northwest catered to the forest industry, making footwear for loggers and wildland firefighters. Here are three you should know. Read the Story

Note: Purchasing products through our links may earn us a portion of the sale, which supports our editorial team’s mission. Learn more here.

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