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Chelsea Boots for Men

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Ivan Chelsea Leather Boot

HAUTELOOK, A NORDSTROM COMPANY

Ivan Chelsea Leather Boot

$160 $90

Sizing: True to size. M=standard width. Burnished square toe. Solid vamp. Quarter brogue detail. Dual goring. Back pull-tab. Padded footbed. Stacked heel. Approx. 4.5" shaft height, 13" opening circumference. Imported buy from Hautelook
Pembrey Polished-Leather Boots - Men - Black

PAUL SMITH

Pembrey Polished-Leather Boots - Men - Black

$795 $398

. Paul Smith's 'Pembrey' boots have minimally detailed, polished black leather uppers, so they're smart enough to wear with the brand's suiting, as well as slim jeans. They have sleek almond toes and fasten with concealed zips that make them easy to get on and off. Shown here with Dunhill sweater, Brioni coat, Séfr trousers. buy from Mr Porter
Leather Chelsea Boots - Men - Black

DUNHILL

Leather Chelsea Boots - Men - Black

$850 $510

. Dunhill 's sleek leather Chelsea boots have been made in Italy using the Blake method, the outsoles are stitched directly to the insoles to create a flexible feel. Wear yours with slim tailoring. Shown here with Brunello Cucinelli suit jacket, Brunello Cucinelli suit trousers, William Lockie sweater. buy from Mr Porter
Eden Leather Chelsea Boots - Men - Black

HUGO BOSS

Eden Leather Chelsea Boots - Men - Black

$445 $267

. The logo-jacquard branding on Hugo Boss ' 'Eden' Chelsea boots is so smartly placed, it adds just a subtle point of difference to an otherwise classic silhouette. This pair is made from black full-grain leather that's resistant towards scuffs and scrapes, and set on hefty rubber lug soles. Shown here with Hugo Boss sweater, James Perse T-shirt, Hugo Boss coat, Jean Shop jeans. buy from Mr Porter
Tempus Polished-Leather Chelsea Boots - Men - Brown

OFFICINE CREATIVE

Tempus Polished-Leather Chelsea Boots - Men - Brown

$675 $473

. Officine Creative has been handmaking shoes since 1968 and still applies the same hands-on care and attention today. These 'Tempus' boots have been crafted in Italy from polished-leather that ages beautifully with wear. The pull tabs and elasticated panels make them easy to get on and off. Shown here with Officine Generale trousers, Officine Generale shirt, Officine Generale blazer. buy from Mr Porter
Craftsman Leather Chelsea Boots - Men - Black

R.M.WILLIAMS

Craftsman Leather Chelsea Boots - Men - Black

$495

. R.M. Williams employs some of Australia's best craftsmen. Head of production, Mr Michael Williams, has been with the company since his apprenticeship 40 years ago. He's tried all of the brand's boots and these single-piece ones are his favourite: When you break in a 'Craftsman' and the leather then starts forming to your foot, I find them so comfortable, " he says. The block heels also offer a little more lift than the average. Shown here with RRL jeans, Officine Generale sweatshirt, Aspesi jacket. buy from Mr Porter
Zucca Suede Chelsea Boots - Mens - Brown

MARSÈLL

Zucca Suede Chelsea Boots - Mens - Brown

$1,070 $321

Marsèll - Marsèll's recognisable aesthetic is imprinted onto these camel-brown Zucca Chelsea boots, defined with a distressed finish and a slightly elevated, rounded toe. They're the product of expert Italian shoemaking, crafted from suede and leather for a durable and timeless feel. The fit runs according to size. buy from MATCHESFASHION.COM
Dylan Suede Chelsea Boots - Men - Black

SAINT LAURENT

Dylan Suede Chelsea Boots - Men - Black

$895 $537

. With their elongated silhouette and suede fabrication, SAINT LAURENT's 'Dylan' Chelsea boots have a sophisticated rock 'n' roll attitude. Expertly made in Italy, they're set on stacked Cuban heels and have elasticated slides to avoid stretching the hide. buy from Mr Porter
Tate Chelsea Boot

NORDSTROM RACK

Tate Chelsea Boot

$325 $190

Sizing: True to size. D=standard width, EEE=extra wide width. Round toe. Dual elasticated side goring. Back pull tab. Pull-on style. Lightly padded footbed. Lug sole. Approx. 7" shaft height, 11" opening circumference. Made in USA buy from Nordstrom Rack
First Class Leather Chelsea Boots - Men - Brown

HUGO BOSS

First Class Leather Chelsea Boots - Men - Brown

$445 $267

. Hugo Boss' 'First Class' Chelsea boots are seasonless and appropriate for so many occasions. They're made from smooth dark-brown leather that works with most other colours and have firm yet flexible rubber soles. buy from Mr Porter
Wyatt Patent-Leather Chelsea Boots - Men - Black

SAINT LAURENT

Wyatt Patent-Leather Chelsea Boots - Men - Black

$945 $567

. SAINT LAURENT's signature 'Wyatt' Chelsea boots are updated every season and this patent-leather version feels a little more daring than the first-generation styles. Designed in a streamlined profile with smart Cuban heels, they're buffed to a high shine and fitted with elasticated inserts at the sides for flexibility. Wear them for evening with cigarette jeans and a leather biker. buy from Mr Porter
Bryson Leather Chelsea Boot

NORDSTROM RACK

Bryson Leather Chelsea Boot

$298 $105

A leather Chelsea boot with a wingtip toe offers a refined, chic style into any look. M=medium width. Almond toe. Leather construction. Wingtip brogueing with brogue medallion. Side elastic goring. Side zip closure. Padded footbed. Stacked sole. Approx. 6.5" shaft height, 10.75" opening circumference. Made in Italy buy from Nordstrom Rack
Pointed-toe Suede Chelsea Boots - Mens - Brown

AMIRI

Pointed-toe Suede Chelsea Boots - Mens - Brown

$990 $594

Amiri - Shaped at the front with a pointed toe, Amiri's Chelsea boots are crafted from light brown suede that's supple to the touch. They're equipped with elasticated side gussets and pull tabs on the heel for easy removal. Note the grippy rubber-crepe soles for enhanced traction. buy from MATCHESFASHION.COM
Sam Chelsea Boot

NORDSTROM RACK

Sam Chelsea Boot

$298 $150

Sizing: True to size. M=medium width. Round toe. Side goring detail. Back pull tab. Pull-on style. Leather construction. Lightly padded footbed. Grip sole. Approx. 4.75" shaft height, 12" opening circumference. Imported buy from Nordstrom Rack
Miles Suede Boots - Men - Black

SAINT LAURENT

Miles Suede Boots - Men - Black

$1,195 $478

. SAINT LAURENT has rock 'n' roll in its DNA, and these 'Miles' boots look like styles worn by some of music's most iconic frontmen. They've been expertly made in Italy from black suede with buckled straps that fasten around the ankles, and have discreet zips at the back so you get them on easily. The small stacked heels add a little extra to your stature, too. Shown here with SAINT LAURENT jeans, SAINT LAURENT T-shirt, SAINT LAURENT coat. This item is small to size. See Size & Fit notes. buy from Mr Porter
Crown Suede Chelsea Boots - Mens - Brown

PAUL SMITH

Crown Suede Chelsea Boots - Mens - Brown

$430

Paul Smith - Paul Smith evokes a refined mood with these brown Crown Chelsea boots, a style originally invented by Queen Victoria's cordwainer J. Sparkes-Hall in 1851. They're crafted in Italy from suede with elasticated side gussets and a slim black leather sole set on a stacked heel, then accented with an emerald-green heel tab. buy from MATCHESFASHION.COM
Suede Chelsea Boots - Mens - Black

ALEXANDER MCQUEEN

Suede Chelsea Boots - Mens - Black

$890 $534

Alexander McQueen - Alexander McQueen's black Chelsea boots arrive in brushed suede with subtle well-worn effects, tapping the house's rebellious codes. They're crafted in Italy with a branded canvas pull tab and set on a durable Cuban heel below a small logo-engraved gunmetal plaque. Fit runs true to size. buy from MATCHESFASHION.COM
Tabi Split-Toe Leather Boots - Men - Black

MAISON MARGIELA

Tabi Split-Toe Leather Boots - Men - Black

$1,280

. Mr Martin Margiela designed his signature 'Tabi' boots to create an invisible shoe, one that gives the illusion of a bare foot walking on a chunky heel. Modelled after traditional Japanese split-toe socks, this pair has been crafted in Italy from supple leather with cylindrical heels that are ideal if you're after a little extra height. Shown here with SAINT LAURENT trousers, SAINT LAURENT shirt, SAINT LAURENT jacket. buy from Mr Porter
Rook Washed Suede Chelsea Boot

NORDSTROM RACK

Rook Washed Suede Chelsea Boot

$225 $120

Sizing: Runs narrow: Whole sizes only; for 1/2 sizes, order next size up. M=medium width. Round toe. Washed suede construction. Dual elastic side gores. Pull-on. Approx. 4.25" shaft height, 10.25" opening circumference. Imported buy from Nordstrom Rack
Xander Leather Chelsea Boot

NORDSTROM RACK

Xander Leather Chelsea Boot

$395 $150

Sizing: True to size. M=standard width. Square toe. Leather construction. Dual elastic side panels. Pull-on style. Back pull-tab. Approx. 5" shaft height, 10" opening circumference. Made in Italy buy from Nordstrom Rack
Godfrey Leather Chelsea Boots - Men - Black

CHEANEY

Godfrey Leather Chelsea Boots - Men - Black

$575

. Cheaney 's black 'Godfrey' Chelsea boots are a lasting wardrobe investment, owing to the timeless design and superior construction methods used to craft them. This handmade pair has supple leather uppers that comfortably mould to the shape of your feet with wear and is set on Goodyear-welted soles panelled with rubber for enhanced durability. They're thoughtfully detailed with pull tabs and elasticated sides to ensure you can comfortably slip them on and off. Shown here with Barena trousers, Camoshita blazer, Barena sweater. buy from Mr Porter
Jolly Leather Boots - Men - Black

CHRISTIAN LOUBOUTIN

Jolly Leather Boots - Men - Black

$1,020

. Christian Louboutin's 'Jolly' boots exude the same laid-back and carefree vibe of performers like Messrs Mick Jagger and Harry Styles. Made in Italy from black leather, they have sturdy block heels, classic tapered toes and signature red soles. Wear them with: SAINT LAURENT Jeans, SAINT LAURENT Jacket, SAINT LAURENT T-shirt, SAINT LAURENT Belt. buy from Mr Porter
Kaidon Chelsea Boot

NORDSTROM RACK

Kaidon Chelsea Boot

$255 $110

Sizing: True to size. Pointed toe. Dual side elastic goring. Leather construction. Back pull-tab. Grip sole. Approx. 6.5" shaft height, 9" opening circumference. Imported buy from Nordstrom Rack
Ranchero Steel-Toe Romeo Brown, Size 11 Extra Wide Width

WOLVERINE

Ranchero Steel-Toe Romeo Brown, Size 11 Extra Wide Width

$100 $75

The Ranchero Romeo is a great option for those looking for a boot to wear off and on the job site. With a rubber lug outsole and romeo style, this boot is durable and versatile. Full-grain leather upper and a moisture wicking mesh lining keep your feet comfortable in all temperatures buy from Wolverine
Canon Leather Chelsea Boots - Men - Black

PAUL SMITH

Canon Leather Chelsea Boots - Men - Black

$695

. The simplicity of Chelsea boots means you can wear them with almost everything. Paul Smith 's 'Canon' pair is a true classic, they're made from smooth leather and fitted with elasticated panels and gripped rubber soles that are sturdy and resilient. Shown here with Mr P. trousers, Mr P. jacket, Mr P. sweater. buy from Mr Porter
Boxcalf Chelsea Boots

JM WESTON

Boxcalf Chelsea Boots

$1,235

Created in the strict tradition of Goodyear stitching, these emblematic Boxcalf Chelsea Boots are a J.M. Weston classic. With roots in the equestrian world, these boots are assembled from a single piece of leather. This is a unique and prized design distinguished by its single seam at the back for total comfort. buy from 24S
Gardener Whole-Cut Leather Chelsea Boots - Men - Brown

R.M.WILLIAMS

Gardener Whole-Cut Leather Chelsea Boots - Men - Brown

$495

Chocolate-brown Leather, Pull Tabs, Elasticated Panels, Leather Linings, Goodyear®-welted Soles. R.M. Williams' 'Gardener' Chelsea boots have been handcrafted in Australia from a single piece of leather, ensuring that they're both comfortable and durable. Initially designed as a work boot, this style has oil-resistant Goodyear®-welted soles, which provide exceptional traction and can be easily resoled over years of wear. Shown here with A.P.C. sweater, Incotex blazer, A.P.C. jeans, Mr. Gray socks, Uniform Wares watch. buy from Mr Porter
Logo-Print Leather Boots - Men - Black

FENDI

Logo-Print Leather Boots - Men - Black

$970 $485

. Fendi's Chelsea boots are an easy way to dress up a simple pair of jeans or tailored trousers. Designed with tapered toes and elasticated sides, they've been crafted in Italy from sleek black leather and discreetly printed with the brand's iconic 'FF' monogram at back. Wear it with: Fendi Sweater, Fendi Trousers, Fendi Bracelet, Fendi Bag. buy from Mr Porter
Crown Suede Chelsea Boots - Mens - Dark Brown

PAUL SMITH

Crown Suede Chelsea Boots - Mens - Dark Brown

$595 $297

Paul Smith - Paul Smith's knack for creating smart staples is reflected by these chocolate-brown Crown boots, constructed in a classic Chelsea style. Made in Italy, they feature elasticated side panels and a vivid orange heel tab - a subtle nod to the the British designer's irreverent aesthetic. Fit true to size. buy from MATCHESFASHION.COM
Boxcalf Chelsea Boots

JM WESTON

Boxcalf Chelsea Boots

$1,235

Created in the strict tradition of Goodyear stitching, these emblematic Boxcalf Chelsea Boots are a J.M. Weston classic. With roots in the equestrian world, these boots are assembled from a single piece of leather. This is a unique and prized design distinguished by its single seam at the back for total comfort. buy from 24S
Wyatt Leather Chelsea Boots - Men - Black

SAINT LAURENT

Wyatt Leather Chelsea Boots - Men - Black

$895 $537

. SAINT LAURENT revisits its signature 'Wyatt' boots in so many new colourways and fabrications each season, but this versatile black leather pair is perhaps the wisest investment. They've been impeccably made in Italy with elasticated side panels and are set on Cuban heels. They break at the perfect height to wear with the brand's skinny-fit jeans or tailored trousers. Shown here with SAINT LAURENT jacket, SAINT LAURENT T-shirt. buy from Mr Porter
Polished-Leather Chelsea Boots - Men - Black

OFFICINE CREATIVE

Polished-Leather Chelsea Boots - Men - Black

$700 $490

. Officine Creative 's Chelsea boots have been crafted in Italy from polished black leather that'll develop its own unique patina with time. They're set on rubber-injected soles stamped on the base with 'Join the Navy'. The zip fastenings make them easy to get on and off. Shown here with Barena coat, Barena sweater, Officine Generale trousers. buy from Mr Porter
Ortega ankle boots

EYTYS

Ortega ankle boots

$530

These Ortega women's boots from Eytys are crafted in embossed brown faux snakeskin and feature elasticated gussets at the side together with two purple pull-tabs for an easy slip-on fit. The thick rubber sole is in two different shades of brown. buy from 24S
Boxcalf Chelsea Boots

JM WESTON

Boxcalf Chelsea Boots

$1,235

Created in the strict tradition of Goodyear stitching, these emblematic Boxcalf Chelsea Boots are a J.M. Weston classic. With roots in the equestrian world, these boots are assembled from a single piece of leather. This is a unique and prized design distinguished by its single seam at the back for total comfort. buy from 24S
Ortega ankle boots

EYTYS

Ortega ankle boots

$530

These Ortega women's boots from Eytys are crafted in embossed brown faux snakeskin and feature elasticated gussets at the side together with two purple pull-tabs for an easy slip-on fit. The thick rubber sole is in two different shades of brown. buy from 24S
Presley ankle boots

LEMON JELLY

Presley ankle boots

$135 $67

Fashion brand Lemon Jelly demonstrates their sophisticated style not only in the comfortable shape and unique choice of textures in their Presley ankle boots, but also in their choice of complementary textures and colourway. buy from 24S
Genie ankle boots

CHURCH'S

Genie ankle boots

$519

Church's Genie ankle boots are urban shoes with an androgynous style, highlighting the brand's skill with luxury fabric and simple design. buy from 24S
Lambourne Textured-Leather Boots - Men - Brown

EDWARD GREEN

Lambourne Textured-Leather Boots - Men - Brown

$1,685 $1,011

. Each pair of Edward Green shoes undergoes a meticulous crafting process that's pretty much stayed the same for the past century. Made at the brand's Northamptonshire factory, these 'Lambourne' boots have been cut, moulded and finished on signature '82' lasts distinguished by the elegant almond-toe shape. The 'Utah' textured-leather uppers will only get better with age. Shown here with Thom Sweeney jacket, Kingsman trousers, Boglioli shirt, Kingsman sweater, Drake's pocket square. buy from Mr Porter
Emory Leather Chelsea Boots - Men - Black

OFFICINE CREATIVE

Emory Leather Chelsea Boots - Men - Black

$665 $333

. Officine Creative has maintained the same high levels of quality since 1968, which is why each pair of shoes is meticulously handmade by Italian artisans. These Chelsea boots are crafted from soft leather with a smart polished finish and fitted with stretchy elasticated inserts to make them easier to pull on and off. buy from Mr Porter
Dylan Tortoiseshell-Effect Patent-Leather Chelsea Boots - Men - Brown

SAINT LAURENT

Dylan Tortoiseshell-Effect Patent-Leather Chelsea Boots - Men - Brown

$945 $567

. Updated in slick tortoiseshell-effect patent-leather, SAINT LAURENT's signature 'Dylan' boots have a Western-inspired shape and stacked Cuban heels. The elasticated side panels mean they'll sit nicely beneath slim-fit trousers. buy from Mr Porter
Craftsman Leather Chelsea Boots - Men - Brown

R.M.WILLIAMS

Craftsman Leather Chelsea Boots - Men - Brown

$495

Chestnut-brown Leather, Pull Tabs, Elasticated Panels, Leather Linings, Goodyear®-welted Leather And Rubber Soles. Made by hand in the brand's Adelaide factory, these R.M. Williams boots typify the label's impeccable craftsmanship and lasting quality. Based on an outback riding boot designed in 1932, this rich chestnut-brown pair is sure to make a stylish impression in town. Fully lined and complete with resilient Goodyear®-welted soles, they'll become an indispensable part of your everyday wardrobe. Shown here with RRL shirt, Barena blazer, RRL jeans, Tomas Maier T-shirt. buy from Mr Porter
Crepe-sole Leather Chelsea Boots - Mens - Black

BOTTEGA VENETA

Crepe-sole Leather Chelsea Boots - Mens - Black

$1,090

Bottega Veneta - The beige crepe soles that ground Bottega Veneta's black leather Chelsea boots were seen throughout the Resort 2020 lookbook. They're made in Italy with elasticated side gussets and a coordinating heel tab. buy from MATCHESFASHION.COM
Gloucester Suede Boots - Men - Brown

BELSTAFF

Gloucester Suede Boots - Men - Brown

$550 $220

. Belstaff's 'Gloucester' boots are meant to look just as good a little scuffed up as they do right out of the box. Crafted in Italy from dark-brown suede, they have practical side zip fastenings and durable rubber-lug soles that provide exceptional grip, even when riding. buy from Mr Porter
Arlo Leather Chelsea Boots - Mens - Brown

GRENSON

Arlo Leather Chelsea Boots - Mens - Brown

$300 $210

Grenson - The Arlo is a brand-new silhouette for Grenson, shown here in a mahogany-brown leather rendition. It reworks the classic Chelsea boot silhouette with traditional patterned brogueing and a thick Richfield Commando sole. Runs true to size. buy from MATCHESFASHION.COM
Canon Leather Chelsea Boots - Men - Brown

PAUL SMITH

Canon Leather Chelsea Boots - Men - Brown

$695

. Paul Smith is a pro at creating classic footwear that's easy to dress up and down, like these 'Canon' Chelsea boots. Expertly made in Italy, they have dark-brown suede uppers fitted with pull tabs and elasticated sides, so you can easily get them on. Shown here with John Smedley sweater, Paul Smith trousers, Mr P. coat. buy from Mr Porter
Leon Exaggerated-sole Leather Chelsea Boots - Mens - Black

GUCCI

Leon Exaggerated-sole Leather Chelsea Boots - Mens - Black

$980

Gucci - Gucci's black Leon Chelsea boots are set onto a chunky tread sole reminiscent of classic hiking styles creating a modern hybrid silhouette. They're crafted in Italy from smooth leather accented with a red and green rubber logo to the heel equipped with elasticated inserts and a durable rubber toe cap. buy from MATCHESFASHION.COM
Yak Waterproof 6" Boot Brown, Size 8 Extra Wide Width

WOLVERINE

Yak Waterproof 6" Boot Brown, Size 8 Extra Wide Width

$110 $90

The Wolverine Yak Chelsea boot is the perfect easy on, easy off boot for unpredictable days. Featuring a barnyard acid resistant leather with TPU shell upper, this boot is waterproof, and can be worn on construction sites with a steel toe, or around town with the soft toe version. buy from Wolverine
Crown Leather Chelsea Boots - Mens - Black

PAUL SMITH

Crown Leather Chelsea Boots - Mens - Black

$595 $357

Paul Smith - Paul Smith's black Crown Chelsea boots are the label's rendition of the classic silhouette that has been a wardrobe staple since the 19th century. They're crafted in Italy from soft leather and feature a elasticated side panels for a flexible fit, while the red heel tab nods to the designer's irreverent attitude. Runs true to size. buy from MATCHESFASHION.COM