Chelsea Boots for Men
Diemme
Balbi Suede And Rubber Chelsea Boots - Mens - Black
$349
At Matchesfashion.com
Diemme - Diemme's black Balbi boots have a hybrid silhouette which blends the traditional Chelsea style with hiking boots, making them ideal for winter weather conditions. They're crafted from textured suede and rubber with elasticated side panels, while they rest on a durable rubber tread sole.. BUY FROM MATCHESFASHION.COM
Alexander Mcqueen
Hybrid Chelsea Boot - Item 586198WHX521066
$624
At Alexander Mcqueen
Black shiny calfskin Chelsea boot with an oversized rubber sole. The boot features red elastic side panels. Boot silhouette with a round toe shape. Finished with an Alexander McQueen signature in contrast on the ribbon tabs.. BUY FROM ALEXANDER MCQUEEN
Cheaney
Godfrey Suede Chelsea Boots - Mens - Tan
$530
At Matchesfashion.com
Cheaney - Cheaney's tan suede Godfrey boots are a refined interpretation of the classic Chelsea style, which was first designed by Mr J Sparkes-Hall at the request of Queen Victoria. They're handmade in Northamptonshire, England with an elasticated gusset and leather pull tab, then rest on a stacked heel.. BUY FROM MATCHESFASHION.COM
Saint Laurent
Army Glossed-leather Ankle Boots - Black
$995
At Net-a-porter
SAINT LAURENT's 'Army' boots are modeled after classic Chelsea styles and detailed with a buckled crisscross strap reminiscent of ones you'd see on monk-strap shoes. They've been made in Italy from panels of black glossed-leather and set on comfortable 30mm heels. Wear yours with everything from feminine dresses to jeans. - Heel measures approximately 30mm/ 1 inch - Black glossed-leather (Calf) - Buckle fastening at side - Made in Italy. BUY FROM NET-A-PORTER
Hunter Boots
Refined Slim Fit Chelsea Boots
$155
At Hunter
*Size/Fit Summary: True to size, Slim fit. If you are in-between sizes or want to wear a thick sock, it is recommended to size up* With a slimmer fit ideal for city-living, the Men's Refined Chelsea features a tailored shape and moulded footbed for everyday wear. A rework of the classic ankle boot, each boot is ready for rain and handcrafted from natural rubber which has been vulcanized for superior protection. Retaining the iconic features of the traditional Chelsea, elasticated gussets and a nylon pull tab make for easy wear. Perfect for everything from city commuting to last minute lunches, this classic black boot is a wet weather essential. We recommend that all Hunter Chelsea boots be worn with Hunter Chelsea socks, which have been technically designed to protect the wearer's skin from contact with rubber in specific areas.. BUY FROM HUNTER
John Lobb
Lawry Suede Chelsea Boots - Mens - Brown
$1,980
At Matchesfashion.com
John Lobb - John Lobb's brown suede Lawry chelsea boots are meticulously crafted in the UK using the same traditional techniques that have been followed by the label since 1849. The timeless silhouette features elasticated side inserts, a grosgrain heel pull tab and tan leather lining to ensure a smooth and comfortable fit. Fits true to size.. BUY FROM MATCHESFASHION.COM
Nordstrom Rack
ALLSAINTS Noble Suede Chelsea Boot at Nordstrom Rack
$335 $140
At Nordstrom Rack
Runs Narrow, suggested to size up. M=standard width. Round toe. Solid vamp. Hidden side goring. Suede construction. Pull-on. Padded footbed. Approx. 5.7" shaft height, 10.2" opening circumference. Grip sole. Imported. BUY FROM NORDSTROM RACK
Santoni
Scarlett Leather Ankle Boots - Mens - Dark Brown
$949
At Matchesfashion.com
Santoni - Santoni's dedication to time-honoured craftsmanship is reflected in the meticulous construction of these brown Scarlett ankle boots. They're crafted in Italy from soft nubuck leather, with a glossy heel and toe cap shaded in a darker hue lending a lived-in appearance, then rest on a low-stacked heel with a side-zip fastening.. BUY FROM MATCHESFASHION.COM
Loeffler Randall
Bridget Croc-effect Patent-leather Chelsea Boots - Black
$395
At Net-a-porter
Loeffler Randall's Chelsea boots are the shoes you'll want to wear with everything this season. Made from glossy croc-effect patent-leather, they have a chunky rubber sole and elasticated inserts for easy on and off. They'll look just as good with a floral dress as they will with cargo pants or jeans.. BUY FROM NET-A-PORTER
Bottega Veneta
Transparent-sole Leather Chelsea Boots - Mens - Brown
$1,150
At Matchesfashion.com
Bottega Veneta - Chelsea boots were introduced in the 19th century and the transparent rubber sole on Bottega Veneta's coffee-brown silhouette provides them with a modern twist. They're crafted in Italy from polished leather to a round-toe profile, then finished with a heel pull and elasticated side panels. Tap into the house's sophisticated codes by styling them with monochrome separates.. BUY FROM MATCHESFASHION.COM
Hautelook, A Nordstrom Company
Dr. Scholl's Levine Side Zip Chelsea Boot at Nordstrom Rack
$80 $50
At Hautelook
A sturdy faux leather boot features an elastic side gore, easy side zip, cushioned insole, and secure lug outsole for superior comfort. This eco-conscious design includes a fabric toe box, linings and topcloth made from recycled bottles, and heel counter made from recycled materials crafted using water-saving dyeing techniques. Sizing: M=standard width. Round toe. Faux leather upper. Inset side goring. Side zip closure. Anatomical cushion insole. Goodyear welt. Lug sole. Imported. BUY FROM HAUTELOOK
Gucci
Dracma Gg-logo Leather Boots - Mens - Black
$1,090
At Matchesfashion.com
Gucci - Gucci's black Dracma boots see the sartorial staple fused with a loafer silhouette. They're made in Italy from glossy patent leather with a subtle cracked effect and discreet inside zips, then feature a gold and blue GG-logo strap across the vamp. Wear them as a streamlined accent to knitwear and denim.. BUY FROM MATCHESFASHION.COM
Hautelook, A Nordstrom Company
Florsheim Chalet Plain Toe Leather Chelsea Boot at Nordstrom Rack
$125 $80
At Hautelook
A timeless Chelsea boot is crafted from leather and features welt stitching and a padded footbed for style and all-day comfort.M=standard width. Plain toe. Leather construction. Dual elastic gore panels. Heel pull tab. Goodyear welt stitching. Lightly padded footbed. Low stacked heel. Imported. BUY FROM HAUTELOOK
Alexander Mcqueen
Hybrid Exaggerated-sole Leather Chelsea Boots - Mens - Black Red
$650
At Matchesfashion.com
Alexander McQueen - Alexander McQueen's AW20 collection is emblazoned with vivid red accents, such as the striking elasticated gusset defining these black Hybrid Chelsea boots. They're made in Italy from smooth leather with an embroidered heel tab and an exaggerated rubber sole.. BUY FROM MATCHESFASHION.COM
Sam Edelman
Laguna Chelsea Boot Sesame Leather
$150
At Sam Edelman
A heavily lugged sole with a utilitarian style update to a classic Chelsea boot . Waterproof. Pull on with elastic gore insets. Closure: Pull On. Toe: Closed toe. Heel height: 1.5 inches. Material: Leather. Insole: Synthetic.. BUY FROM SAM EDELMAN
Valentino Garavani
Buckle-strap Leather Chelsea Boots - Mens - Black
$995
At Matchesfashion.com
Valentino Garavani - Utilitarian codes are ingrained in Valentino Garavani's approach to design and the buckled strap on these black Chelsea boots are a fine example. They're crafted in Italy from supple leather to a round toe profile with elasticated sides and a heel tab, then set atop a chunky rubber sole. Style it with a double-breasted jacket and straight-leg trousers to complete the sophisticated silhouette.. BUY FROM MATCHESFASHION.COM
Hautelook, A Nordstrom Company
Karl Lagerfeld Paris Side Zip Chelsea Boot at Nordstrom Rack
$295 $130
At Hautelook
An elastic side gore and a side zip entry allow for ease of fit and movement in this soft suede Chelsea boot.Sizing: True to size. Square burnished toe. Suede construction. Side elastic side gore. Side zip closure. Cushioned insole. Imported. BUY FROM HAUTELOOK
Tricker's
Henry Trek-sole Suede Chelsea Boots - Mens - Tan
$481
At Matchesfashion.com
Tricker's - Set on a chunky rubber trek sole, these brown Henry Chelsea boots from Tricker's fuse sartorial and workwear codes for a fresh approach to the season's hiking-inspired footwear trend. They're made in the label's Northamptonshire factory from soft suede that's framed by brogueing perforations and feature elasticated side gussets and matching heel pulls.. BUY FROM MATCHESFASHION.COM
Christian Louboutin
Machcroche Leather Chelsea Boots - Black
$995
At Net-a-porter
Christian Louboutin's 'Marchacroche' Chelsea boots are designed with an elastic panel that wraps around the ankle for a comfortable, flexible fit. They've been made in Italy from supple black leather and have a rounded toe and lug sole with a 35mm heel. The pull tabs allow them to slide on and off easily. Wear yours with anything from denim to midi dresses.. BUY FROM NET-A-PORTER
Bottega Veneta
Panelled-leather Chelsea Boots - Mens - Green
$1,100
At Matchesfashion.com
Bottega Veneta - The panelled uppers of Bottega Veneta's dark green Chelsea boots nod to the house's affinity for innovative construction, which is noted in each collection through the iconic Intrecciato weave. They're shaped from glossy leather to a round-toe silhouette with elasticated side panels and heel pulls, then set on a low stacked heel. Tap the house's contemporary verve by pairing them with relaxed tailoring.. BUY FROM MATCHESFASHION.COM
Hautelook, A Nordstrom Company
NUNN BUSH Fuse Leather Plain Toe Chelsea Boot - Wide Width Available at Nordstrom Rack
$100 $70
At Hautelook
A layered leather Chelsea boot featuring a comfort gel cushioned insole delivers polished style. Sizing: True to size. M=standard width, W=wide width. Plain toe. Layered leather construction. Side inset elastic gores. Pull-on style. Back pull-tab. Comfort gel cushioning. Goodyear welt. Low block heel. Grip sole. Imported. BUY FROM HAUTELOOK
Bottega Veneta
Panelled-leather Chelsea Boots - Mens - Black
$1,100
At Matchesfashion.com
Bottega Veneta - Traditional Chelsea boots were popularised in the mid-20th century - named after an association with London's King's Road - and Daniel Lee updates this black pair with a panelled construction. They're crafted in Italy from shiny leather and elasticated side panels for an easy fit, finished with a low-stacked heel. Underpin the contemporary mood by teaming them with tailored separates.. BUY FROM MATCHESFASHION.COM
Saint Laurent
West Leather Ankle Boots - Black
$995
At Net-a-porter
SAINT LAURENT's 'West' boots are a feminine take on cowboy styles - note the elegant pointed toes and Cuban heels. They've been made in Italy from black leather and fitted with side zippers for a sleek fit. Wear it with: SAINT LAURENT Jeans, SAINT LAURENT T-shirt, SAINT LAURENT Blazer. - Heel measures approximately 45mm/ 2 inches - Black leather (Calf) - Zip fastening along side - Made in Italy. BUY FROM NET-A-PORTER
Cheaney
Godfrey Suede Chelsea Boots - Mens - Khaki
$530
At Matchesfashion.com
Cheaney - Cheaney's khaki-green Godfrey Chelsea boots are a heritage silhouette from the Northamptonshire-based label, which has been crafting exquisite footwear for over a century. They're made in the UK from soft suede with brown elasticated side gussets, a grosgrain heel pull that's woven with the founder Joseph Cheaney's name and rest on a stacked leather heel and sole.. BUY FROM MATCHESFASHION.COM
See By ChloÉ
Logo-debossed Patent-leather Chelsea Boots - Black
$415
At Net-a-porter
See By Chloé's Chelsea boots have been made at the brand's atelier in Spain from black patent-leather and set on lug soles that offer plenty of grip. Elasticated panels and pull tabs make them easier to slip on and off. They're debossed at the back with a subtle logo. Wear it with: 3.1 Phillip Lim Sweater, Andersson Bell Skirt, Khaite Clutch. - Heel measures approximately 50mm/ 2 inches with a 20mm/ 1 inch platform - Black patent-leather (Calf) - Pull on - Made in Spain. BUY FROM NET-A-PORTER
Hautelook, A Nordstrom Company
Hawke & Co. Skylark Chelsea Boot at Nordstrom Rack
$125 $35
At Hautelook
Round toe. Suede with contrasting textile construction. Pull-on with dual elasticated side panels. Lightly padded footbed. Back pull-tab. Stitched welt midsole. Approx. 4.5" shaft height, 10" opening circumference. ImportedThis item cannot be shipped to Canada.. BUY FROM HAUTELOOK
Santoni
Bohemian Suede Chelsea Boots - Mens - Dark Brown
$931
At Matchesfashion.com
Santoni - Santoni's aptly named Bohemian boots are a casual interpretation of the traditional Chelsea style, first crafted in the 19th century. They're expertly made in the label's native Italy from soft suede with the style's signature elasticated panels and almond toe, then sit atop a stacked heel and sole.. BUY FROM MATCHESFASHION.COM
Bottega Veneta
The Lean Leather Chelsea Boots - Mens - Black
$1,550
At Matchesfashion.com
Bottega Veneta - Bottega Veneta's black The Lean Chelsea boots are characterised by an angular, stacked heel, which draws inspiration from Western-style tropes. They're made in Italy from butter-soft leather to a square-toe profile and are constructed with an exaggerated outsole. Tap into the house's sophisticated codes by wearing them with monochromatic separates.. BUY FROM MATCHESFASHION.COM
Diemme
Balbi Suede And Rubber Chelsea Boots - Mens - Navy
$349
At Matchesfashion.com
Diemme - Diemme's navy Balbi boots are structured with an embossed-rubber vamp providing a contemporary take on classic Chelsea silhouettes with added durability. They're crafted at the Calzaturificio Diemme factory in Onè di Fonte, Veneto - where all the label's shoes are made - from soft suede with elasticated side panels and rest on a rubber tread sole.. BUY FROM MATCHESFASHION.COM
Martine Rose
Square-toe Patent-leather Boots - Mens - Black
$590
At Matchesfashion.com
Martine Rose - London-based designer Martine Rose's subversive perspective is channeled by these black patent-leather boots. They're shaped with a sharp square toe which is accentuated by the wide sole and finished with elasticated side panels which makes them easy to slip on and off.. BUY FROM MATCHESFASHION.COM
Hautelook, A Nordstrom Company
Born Pike Leather Chelsea Boot at Nordstrom Rack
$145 $72
At Hautelook
Sizing: True to size. M=standard width. Round toe. Leather with contrasting textile construction. Dual elasticated side panels. Pull-on style. Back pull-tab. Padded footbed. Grip sole. Approx. 5.5" shaft height. Imported. BUY FROM HAUTELOOK
Alexander Mcqueen
Hybrid Raised-sole Leather Chelsea Boots - Mens - Black
$790
At Matchesfashion.com
Alexander McQueen - The chunky raised rubber sole grounding Alexander McQueen's black Hybrid Chelsea boots is a house signature, inspired by hiking gear. They're made in Italy with an elasticated gusset and embroidered heel tab.. BUY FROM MATCHESFASHION.COM
Jimmy Choo
Rourke 45 Embellished Patent-leather Chelsea Boots - Black
$850
At Net-a-porter
Chelsea boots are loved for their versatility - you can pair them with so many different outfits. Made in Italy from patent-leather, Jimmy Choo's sleek 'Rourke' style has elasticated sides and a slim branded plate on the back. The comfortable heel will add a little height. Wear it with: Self-Portrait Dress, Totême Tank, Totême Jeans, Bottega Veneta Rings. - Heel measures approximately 45mm/ 2 inches - Black patent-leather (Calf) - Pull on - Made in Italy. BUY FROM NET-A-PORTER
Ranjo Tread-sole Waxed-leather Chelsea Boots - Mens - Black
$635
At Matchesfashion.com
Jacques Soloviere - Jacques Solovièr's black Ranjo boots are for those with a style-forward spirit. They're impeccably crafted in Italy from waxed leather fitted with pull tabs and elasticated panels and rest on a welted 3cm rubber tread sole.. BUY FROM MATCHESFASHION.COM
Burberry
Vintage Check Detail Coated Canvas Chelsea Boots, Size: 41, Black
$690
At Burberry
Italian-made coated canvas Chelsea boots reworked with archival Vintage check side panels. The style is capped with a polished overshoe inspired by rain boots and a cross-detailed tread referencing our iconic check. Upper: 45% cotton, 25% polyester, 10% polyurethane, 5% calf leather, 5% polyamide, 5% polypropylene, 5% synthetic rubber Lining: 75% polyester, 20% sheep leather, 5% synthetic rubber Sole: 100% polyurethane Slip-on style with pull tabs Rounded toe Embossed Burberry lettering at heel Made in Italy. BUY FROM BURBERRY
Nordstrom Rack
Frye Peyton Chelsea Boot at Nordstrom Rack
$278 $140
At Nordstrom Rack
A classic leather Chelsea boot with a back pull-tab offers a versatile, en vogue style. Sizing: True to size. M=standard width. Round toe. Dual side elastic goring. Leather construction. Back pull-tab. Topstitched detail. Approx. 5" shaft height, 10.5" opening circumference. Imported. BUY FROM NORDSTROM RACK
Bottega Veneta
Leather Chelsea Boots - Mens - Black
$1,100
At Matchesfashion.com
Bottega Veneta - The time-honoured Chelsea boot silhouette was first created for Queen Victoria's riding kit, the elongated silhouette of which is reflected in Bottega Veneta's classic black style. The streamlined profile has been expertly crafted in Italy from leather that's buffed to a soft shine and fitted with elasticated side panels for easy dressing, then set on a robust stacked heel.. BUY FROM MATCHESFASHION.COM
Jennifer Chamandi
Gianni Leather Ankle Boots - Black
$845
At Net-a-porter
A self-proclaimed perfectionist, Jennifer Chamandi considers every last detail while designing her elegant footwear. These 'Gianni' ankle boots have been crafted in Italy from supple black leather and set on low block heels, which are threaded with the label's signature 'eye of the needle'. The straps can be removed if you prefer. - Heel measures approximately 25mm/ 1 inch - Black leather - Zip fastening along side - Made in Italy. BUY FROM NET-A-PORTER
Hunter Boots
Refined Slim Fit Chelsea Boots
$155
At Hunter
*Size/Fit Summary: True to size, Slim fit. If you are in-between sizes or want to wear a thick sock, it is recommended to size up* With a slimmer fit ideal for city-living, the Men's Refined Chelsea features a tailored shape and moulded footbed for everyday wear. A rework of the classic ankle boot, each boot is ready for rain and handcrafted from natural rubber which has been vulcanized for superior protection. Retaining the iconic features of the traditional Chelsea, elasticated gussets and a nylon pull tab make for easy wear. Perfect for everything from city commuting to last minute lunches, this classic boot in a neutral navy shade is a wet weather essential. We recommend that all Hunter Chelsea boots be worn with Hunter Chelsea socks, which have been technically designed to protect the wearer's skin from contact with rubber in specific areas.. BUY FROM HUNTER
Alexander Mcqueen
Hybrid Exaggerated-sole Suede Chelsea Boots - Mens - Black
$650
At Matchesfashion.com
Alexander McQueen - Alexander McQueen's black Hybrid Chelsea boots are set on an exaggerated rubber sole that's reminiscent of the house's signature chunky trainers. They're crafted in Italy from brushed suede with a silver logo-jacquard heel tab and lined in leather for a smooth fit.. BUY FROM MATCHESFASHION.COM
Nordstrom Rack
Magnanni Foster Suede Chelsea Boot at Nordstrom Rack
$398 $200
At Nordstrom Rack
A classic suede Chelsea boot delivers polished style and versatility. M=standard width. Round toe. Dual side elastic goring. Suede construction. Topstitched detail. Pull-on. Welt midsole trim. Back pull-tab. Approx. 5.5" shaft height, 11" opening circumference. Imported. BUY FROM NORDSTROM RACK
Guidi
Distressed Suede Chelsea Boots - Mens - Black
$950
At Matchesfashion.com
Guidi - Guidi subjects its shoes to a painstaking and heavily manual process to give them the vintage look that's embodied by these black Chelsea boots. They're made in Pescia, Italy from distressed suede with a pull tab and elasticated side panels, then rest on a leather sole and heel that can be replaced by your local cobbler with the provided Vibram-rubber soles.. BUY FROM MATCHESFASHION.COM
Alexander Mcqueen
Silver-cap Leather Chelsea Boots - Mens - Black
$950
At Matchesfashion.com
Alexander McQueen - These black leather Chelsea boots are elevated with a silver Cuban heel, a key accent throughout Alexander McQueen's recent collections. They're constructed in Italy with embroidered pull tabs and elasticated gussets. Tap the label's signature narrow suiting and wear them to offset slim tailored trousers.. BUY FROM MATCHESFASHION.COM
Yuketen
Pancho Suede-leather Chelsea Boots - Mens - Brown
$498
At Matchesfashion.com
Yuketen - Founded in 1989 by Yuki Matsuda, Yukuten employs traditional techniques with a contemporary twist to create these golden brown Pancho Chelsea boots. They're handcrafted by artisans from suede leather to a reinforced point-toe silhouette that's sat on a Goodyear-welted sole, then finished with branded pull tabs at the front and back.. BUY FROM MATCHESFASHION.COM
Cos
CHUNKY LEATHER CHELSEA BOOTS
$250
At Cos
The Chelsea boot, modernized. Designed from smooth leather, these boots will add a stylish twist to cold-weather looks. - Round toe - Elasticated panels at the side - Pull-on design - Leather strap at the back - Chunky rubber sole 100% Leather / Lining: 100% Leather / Sole: 100% Thermoplastic rubber. BUY FROM COS
Alexander Mcqueen
Hybrid Chelsea Boot - Item 586198WHX521000
$624
At Alexander Mcqueen
Black shiny calfskin Chelsea boot with an oversized rubber sole. The boot features tonal elastic side panels. Boot silhouette with a round toe shape. Finished with an Alexander McQueen signature in contrast on the ribbon tabs.. BUY FROM ALEXANDER MCQUEEN
Bottega Veneta
Leather Chelsea Boots - Mens - Brown
$1,100
At Matchesfashion.com
Bottega Veneta - The Chelsea boot was originally an essential element of Victorian riding uniforms, a heritage that's reflected in the elevated silhouette of Bottega Veneta's mahogany-brown pair. They're crafted in Italy from polished leather with elasticated black side inserts, then set on a rubber heel and sole.. BUY FROM MATCHESFASHION.COM
Rag & Bone
Shaye Patent-leather Chelsea Boots - Black
$525
At Net-a-porter
rag & bone's 'Shaye' Chelsea boots are so practical and also right on trend. They're made from glossy patent-leather and set on a chunky rubber sole that will give you a little extra height. The elasticated side panels make them easy to pull on and off. Wear it with: Khaite Sweater, we11done Jacket, BERNADETTE Skirt, Khaite Clutch. - Heel measures approximately 55mm/ 2 inches - Black patent-leather (Cow) - Pull on - Imported. BUY FROM NET-A-PORTER