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Chelsea Boots for Men

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Leather Chelsea Boots - Mens - Brown

Bottega Veneta

Leather Chelsea Boots - Mens - Brown

£805

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
Lawry Leather Chelsea Boots - Mens - Black

John Lobb

Lawry Leather Chelsea Boots - Mens - Black

£1,365

At Matchesfashion.com

John Lobb - These black Chelsea boots are meticulously crafted in John Lobb's Northampton workshop using the same techniques employed since the label's founding in 1849. They're crafted from smooth, polished leather and rest on leather soles, detailed with elasticated side panels.. Buy from MATCHESFASHION.COM
Lambert Leather Chelsea Boots - Mens - Black

Paul Smith

Lambert Leather Chelsea Boots - Mens - Black

£395

At Matchesfashion.com

Paul Smith - Paul Smith's black leather Lambert boots are a sophisticated iteration of the traditional Chelsea style which were first created by Queen Victoria's shoemaker J. Sparks-Hal after the monarch requested a practical style for horse riding. They're made from leather with an elasticated gusset and grosgrain heel tab, then rest on a rubber sole.. Buy from MATCHESFASHION.COM
Balbi Suede And Rubber Chelsea Boots - Mens - Navy

Diemme

Balbi Suede And Rubber Chelsea Boots - Mens - Navy

£250

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
Stacked-heel Leather Chelsea Boots - Mens - Black

Saint Laurent

Stacked-heel Leather Chelsea Boots - Mens - Black

£790

At Matchesfashion.com

Saint Laurent - A high-rise stacked sole and streamlined almond-shaped toes imbue these black Chelsea boots with Saint Laurent's mid-century inspired rebelliousness. Crafted in Italy from finely grained leather, they have an ankle-high topline and elasticated panels that make them easy to slip on and off. Frame them with close-fitting jeans.. Buy from MATCHESFASHION.COM
Bozo Megatooth Scratched-leather Chelsea Boots - Mens - Black

Rick Owens

Bozo Megatooth Scratched-leather Chelsea Boots - Mens - Black

£945

At Matchesfashion.com

Rick Owens - Rick Owens' black Bozo Megatooth Chelsea boots are part of an AW20 footwear offering that taps on the unwavering chunky-shoe trend. They're made in Italy from leather which is distressed to emulate the scratches of a cat and completed with ample elasticated panels and an exaggerated rubber sole.. Buy from MATCHESFASHION.COM
Pancho Suede-leather Chelsea Boots - Mens - Brown

Pancho Suede-leather Chelsea Boots - Mens - Brown

£450

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
Declan Leather Chelsea Boots - Mens - Black

Grenson

Declan Leather Chelsea Boots - Mens - Black

£285

At Matchesfashion.com

Grenson - Grenson's black Declan Chelsea boots are a timeless silhouette, ideal for underpinning year-round smart and casual edits - a true wardrobe staple. They're exquisitely made from polished leather with elasticated side gussets and a woven heel pull for ease of wear, and they rest on a small stacked heel and leather sole.. Buy from MATCHESFASHION.COM
Tabi Split-toe Leather Chelsea Boots - Mens - Black

Maison Margiela

Tabi Split-toe Leather Chelsea Boots - Mens - Black

£805

At Matchesfashion.com

Maison Margiela - Maison Margiela's black Tabi Chelsea boots reinterpret the label's signature split-toe silhouette, a design inspired by 15th century Japanese socks and debuted on the 1988 runway. They're crafted from glossy patent leather with elasticated side panels and rest on a low stacked heel and leather sole.. Buy from MATCHESFASHION.COM
Colin Leather Chelsea Boots - Mens - Dark Brown

Santoni

Colin Leather Chelsea Boots - Mens - Dark Brown

£800

At Matchesfashion.com

Santoni - Santoni anchors these brown Colin boots with a practical tread sole, imbuing the classic Chelsea style with a contemporary note. They're expertly made in Italy from patent leather with an elasticated gusset and almond toe, then finished with a grosgrain heel tab.. Buy from MATCHESFASHION.COM
Rubber-sole Suede Chelsea Boots - Mens - Brown

Tod's

Rubber-sole Suede Chelsea Boots - Mens - Brown

£498

At Matchesfashion.com

Tod's - The chunky rubber sole of these chocolate-brown Tod's Chelsea boots adds durability to the classic silhouette, which dates to the early 19th century. They're crafted in Italy from panels of smooth suede with a round toe and elasticated sides, then rest on a low stacked heel.. Buy from MATCHESFASHION.COM
Jeffrey Raised-sole Leather Chelsea Boots - Mens - Brown

Burberry

Jeffrey Raised-sole Leather Chelsea Boots - Mens - Brown

£690

At Matchesfashion.com

Burberry - Burberry offers up a directional reworking of the classic Chelsea boot, a style invented by Queen Victoria's personal shoemaker in 1851, with this chocolate-brown Jeffrey pair. They're crafted in Italy from leather with an elasticated side panel and a raised black rubber sole embossed with the label's logo. Note how the Union Jack pull tabs maintain the tongue-in-cheek tone.. Buy from MATCHESFASHION.COM
Panelled-leather Chelsea Boots - Mens - Black

Bottega Veneta

Panelled-leather Chelsea Boots - Mens - Black

£805

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
Transparent-sole Leather Chelsea Boots - Mens - Brown

Bottega Veneta

Transparent-sole Leather Chelsea Boots - Mens - Brown

£845

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
Alda Sport Leather Chelsea Boots - Mens - Burgundy

Hereu

Alda Sport Leather Chelsea Boots - Mens - Burgundy

£390

At Matchesfashion.com

Hereu - Founded by José Luis Bartolomé and Albert Escribano, HEREU's innovative sensibilities are captured through these burgundy Alda Sport shoes which are a hybrid between chelsea boots and moccasins. They're crafted by local artisans in Spain from smooth leather to a square-toe profile and feature dual pull tabs, elasticated side panels and a rubber tread sole.. Buy from MATCHESFASHION.COM
Declan Suede Chelsea Boots - Mens - Tan

Grenson

Declan Suede Chelsea Boots - Mens - Tan

£285

At Matchesfashion.com

Grenson - Grenson's brown Declan boots are cut to a traditional and timeless Chelsea silhouette - named after 1960s socialites who adopted the style during their jaunts around the King's Road in London. It's crafted from sumptuous suede with elasticated side gussets, a woven heel pull and rest on a leather sole and small stacked heel.. Buy from MATCHESFASHION.COM
Melon Spike-embellished Suede Chelsea Boots - Mens - Black

Christian Louboutin

Melon Spike-embellished Suede Chelsea Boots - Mens - Black

£1,165

At Matchesfashion.com

Christian Louboutin - Christian Louboutin's black Melon chelsea boots are defined by the gunmetal studded toe cap that brings a commanding tone to the staple silhouette. They're made in Italy from soft suede with elasticated side gussets and rest on a chunky stacked leather and rubber sole accented by a red stripe, denoting the label's signature hue.. Buy from MATCHESFASHION.COM
Austin Metal Toe-cap Leather Chelsea Boots - Mens - Black

Givenchy

Austin Metal Toe-cap Leather Chelsea Boots - Mens - Black

£1,095

At Matchesfashion.com

Givenchy - The models in Givenchy's AW20 runway show wore square-toed shoes and these black Austin boots channel the graphic mood. They're crafted in Italy from smooth leather with a silver toe cap - drawing on the Western references seen throughout the collection - and slip on easily with the elasticated side panels, then rest on a low-stacked heel. Note the engraved logo which adorns the front of the toe.. Buy from MATCHESFASHION.COM
Crown Leather Chelsea Boots - Mens - Black

Paul Smith

Crown Leather Chelsea Boots - Mens - Black

£395

At Matchesfashion.com

Paul Smith - Paul Smith's black Crown Chelsea boots highlight the designer's ability to create stalwart wardrobe staples. They're crafted in Italy from smooth leather with elasticated side gussets for easy movement and slim stacked heels, then accented with a playful red grosgrain heel tab.. Buy from MATCHESFASHION.COM
Logo-tab Leather Chelsea Boots - Mens - Black

Marni

Logo-tab Leather Chelsea Boots - Mens - Black

£690

At Matchesfashion.com

Marni - Marni's black Chelsea boots are accented with a red logo-jacquard pull tab which reflects the label's colour-blocking aesthetic. They're crafted in Italy from crinkled-effect leather with elasticated side gussets and set on a chunky rubber heel and tread sole. Wear with loose-fitting trousers for a contemporary slant.. Buy from MATCHESFASHION.COM
Custar Suede Chelsea Boots - Mens - Black

Saint Laurent

Custar Suede Chelsea Boots - Mens - Black

£790

At Matchesfashion.com

Saint Laurent - A stacked Cuban heel imbues Saint Laurent's black Custar Chelsea boots with a rebellious edge. They're made in Italy from butter-soft suede with the style's signature elasticated gusset and rounded toe. Slip them on to toughen up a contemporary day edit.. Buy from MATCHESFASHION.COM
Suede Chelsea Boots - Mens - Dark Brown

Brunello Cucinelli

Suede Chelsea Boots - Mens - Dark Brown

£850

At Matchesfashion.com

Brunello Cucinelli - Brunello Cucinelli's quiet sophistication is captured by these brown suede Chelsea boots, which are crafted in Solomeo - the Umbrian hamlet where the label is based. They're accented by a herringbone heel tab and lined with smooth tan leather, then set on low heel.. Buy from MATCHESFASHION.COM
Raised-sole Leather Chelsea Boots - Mens - Black

Alexander Mcqueen

Raised-sole Leather Chelsea Boots - Mens - Black

£590

At Matchesfashion.com

Alexander McQueen - The chunky raised rubber sole grounding Alexander McQueen's black Chelsea boots are a house signature, inspired by hiking gear. They're made in Italy with an elasticated gusset and embroidered heel tab.. Buy from MATCHESFASHION.COM
Almond-toe Leather Chelsea Boots - Mens - Dark Brown

Santoni

Almond-toe Leather Chelsea Boots - Mens - Dark Brown

£715

At Matchesfashion.com

Santoni - Santoni's rich brown Chelsea boots are inspired by silhouettes from the 1960s, where they were popular on London's King's Road in Chelsea, which is where they take their name. They're crafted in Italy from high-shine leather with an almond toe and elasticated side panels, resting on a low-stacked heel.. Buy from MATCHESFASHION.COM
Macon Ii Buckled Leather Boots - Mens - Brown

Ralph Lauren Purple Label

Macon Ii Buckled Leather Boots - Mens - Brown

£1,000

At Matchesfashion.com

Ralph Lauren Purple Label - Ralph Lauren Purple Label's brown leather Macon II boots are accented with buckled straps that recall classic riding attire, an ongoing source of inspiration for the label's refined style. They're made from leather with black lacquered edges accentuating the panelled construction and are shaped with a rounded point toe and stacked heel.. Buy from MATCHESFASHION.COM
Mike Zip-up Suede Chelsea Boots - Mens - Black

Balmain

Mike Zip-up Suede Chelsea Boots - Mens - Black

£750

At Matchesfashion.com

Balmain - Balmain's black Mike boots give the classic Chelsea silhouette a tough, rock 'n' roll reimagining with sleek gunmetal zips on the inside and outside. They're made in Italy from plush suede with an almond-shaped toe, leather lining and a stacked Cuban heel.. Buy from MATCHESFASHION.COM
Topstitched Leather Chelsea Boots - Mens - Black

Toga Virilis

Topstitched Leather Chelsea Boots - Mens - Black

£360

At Matchesfashion.com

Toga Virilis - Toga Virilis's black Chelsea boots are topped with the label's signature Western-inflected topstitching at the pointed toe. They're made from smooth leather with elasticated side panels and a heel pull tab, then set on a sturdy stacked cuban heel and tread sole.. Buy from MATCHESFASHION.COM
Suede Chelsea Boots - Mens - Black

Alexander Mcqueen

Suede Chelsea Boots - Mens - Black

£650

At Matchesfashion.com

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
Transparent-sole Leather Chelsea Boots - Mens - Black

Bottega Veneta

Transparent-sole Leather Chelsea Boots - Mens - Black

£845

At Matchesfashion.com

Bottega Veneta - Bottega Veneta's black Chelsea boots are crafted with a transparent lug sole - offering a modern take on traditional silhouettes which date back to the mid-19th century. The brushed leather uppers are framed by a round toe and inset with elasticated panels which aid a comfortable fit. Channel the house's modern sensibility by teaming them with relaxed tailoring.. Buy from MATCHESFASHION.COM
Melon Spikes Suede Chelsea Boots - Mens - Brown

Christian Louboutin

Melon Spikes Suede Chelsea Boots - Mens - Brown

£1,165

At Matchesfashion.com

Christian Louboutin - Christian Louboutin's brown Melon Spikes Chelsea boots are punctuated with gold spikes around the leather toecap for a bold take on a classic shoe silhouette. They're crafted in Italy with elasticated side gussets and a pull tab for ease of slipping on, then set on a chunky beige and red rubber tread sole. Wear them as a statement finish to tailored separates.. Buy from MATCHESFASHION.COM
Leather Chelsea Boots - Mens - Black

Loewe

Leather Chelsea Boots - Mens - Black

£675

At Matchesfashion.com

Loewe - Loewe's black Chelsea boots are a testament to the Spanish house's leather-working heritage showcased through their refined construction. They're crafted in Italy to a round-toe profile with elasticated sides, then set atop a light brown crepe sole with a low stacked heel.. Buy from MATCHESFASHION.COM
Bohemian Suede Chelsea Boots - Mens - Dark Brown

Santoni

Bohemian Suede Chelsea Boots - Mens - Dark Brown

£680

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
Custar Snake-effect Leather Chelsea Boots - Mens - Black

Saint Laurent

Custar Snake-effect Leather Chelsea Boots - Mens - Black

£880

At Matchesfashion.com

Saint Laurent - Saint Laurent's black Custar boots are a textural interpretation of the traditional Chelsea style. They're made in Italy from snake-effect leather with a rounded toe and an elasticated gusset, then set on a stacked Cuban heel. Choose them as a rebellious grounding to a statement smart edit.. Buy from MATCHESFASHION.COM
Samson Leather Chelsea Boots - Mens - Black

Christian Louboutin

Samson Leather Chelsea Boots - Mens - Black

£965

At Matchesfashion.com

Christian Louboutin - This is a black rendition of Christian Louboutin's Samson Chelsea boots, which were specifically designed for USA actor Brad Pitt. They're crafted in Italy from polished smooth leather with an almond toe and a small stacked heel followed by the distinctive red sole.. Buy from MATCHESFASHION.COM
Scarlett Leather Ankle Boots - Mens - Dark Brown

Santoni

Scarlett Leather Ankle Boots - Mens - Dark Brown

£690

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
Ketsby Studded Leather Chelsea Boots - Mens - Black

Church's

Ketsby Studded Leather Chelsea Boots - Mens - Black

£640

At Matchesfashion.com

Church's - Church's black Ketsby Chelsea boots are cut to a traditional silhouette, then elevated with studded brogue perforations that bring a statement finish. They're made in the UK - the label was founded in 1873 in Northampton and its headquarters remain there today - from polished leather with elasticated side gussets, a heel pull and stacked leather sole.. Buy from MATCHESFASHION.COM
Alpinono Suede Boots - Mens - Brown

Christian Louboutin

Alpinono Suede Boots - Mens - Brown

£925

At Matchesfashion.com

Christian Louboutin - Christian Louboutin takes a smart approach to outdoors influences to create these brown Alpinono boots, set on a chunky rubber tread sole inspired by hiking shoes. They're crafted in Italy from brushed suede with a squared toe and beige leather lining for a comfortable fit. Choose them to complement shirting and denim throughout the week.. Buy from MATCHESFASHION.COM
Exaggerated-sole Leather Chelsea Boots - Mens - Black

Jil Sander

Exaggerated-sole Leather Chelsea Boots - Mens - Black

£790

At Matchesfashion.com

Jil Sander - Jil Sander's black leather Chelsea boots are set atop a chunky Vibram sole, offering a utilitarian interpretation of the traditional style. They're made in Italy with elasticated panels and a round toe, then finished with ankle and heel pull tabs. Slip them on as a contemporary grounding to a tailored edit.. Buy from MATCHESFASHION.COM
Crown Suede Chelsea Boots - Mens - Brown

Paul Smith

Crown Suede Chelsea Boots - Mens - Brown

£395

At Matchesfashion.com

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
Walden Leather Chelsea Boots - Mens - Black

Camperlab

Walden Leather Chelsea Boots - Mens - Black

£250

At Matchesfashion.com

CAMPERLAB - Camperlab's black Walden Chelsea boots unite the label's traditional cobbler expertise with technical elements. They're made from smooth leather with a built-in OrthoLite® insole made from soft foam and recycled rubber for everyday comfort, then set on a chunky rubber sole.. Buy from MATCHESFASHION.COM
Bohemian Leather Chelsea Boots - Mens - Black

Santoni

Bohemian Leather Chelsea Boots - Mens - Black

£740

At Matchesfashion.com

Santoni - Santoni's storied cobbler heritage is united with contemporary aesthetics in these black leather Bohemian boots, specifically with the use of cobalt-blue dégradé across the top edge and front seams. They're crafted in Italy from high-shine smooth leather to a refined almond-toe profile, set with a side zip, then finished with a stacked heel.. Buy from MATCHESFASHION.COM
Distressed Suede Chelsea Boots - Mens - Black

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
Godfrey Suede Chelsea Boots - Mens - Khaki

Cheaney

Godfrey Suede Chelsea Boots - Mens - Khaki

£380

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
Balbi Suede And Rubber Chelsea Boots - Mens - Black

Diemme

Balbi Suede And Rubber Chelsea Boots - Mens - Black

£250

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
Leather Chelsea Boots - Mens - Black

Bottega Veneta

Leather Chelsea Boots - Mens - Black

£805

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
Panelled-leather Chelsea Boots - Mens - Green

Bottega Veneta

Panelled-leather Chelsea Boots - Mens - Green

£805

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
Ellingham Grained-leather Chelsea Boots - Mens - Dark Brown

Church's

Ellingham Grained-leather Chelsea Boots - Mens - Dark Brown

£480

At Matchesfashion.com

Church's - Grenson puts a contemporary spin on these dark brown Ellingham Chelsea boots with the use of a chunky rubber sole. Crafted in the UK with an ankle-height topline from tactile grained leather, they're fitted with streamline elasticated panels and have a capped construction at the almond-shaped toes.. Buy from MATCHESFASHION.COM
Ortega Chunky Leather Chelsea Boots - Mens - Black

Eytys

Ortega Chunky Leather Chelsea Boots - Mens - Black

£390

At Matchesfashion.com

Eytys - Swedish label Eytys - spelt with a Y to reference the Millenial generation born in the 1980s and 90s - is known for its chunky silhouettes, such as the one defining these black Ortega boots. They're crafted from smooth leather with a squared toe and elasticated side panels between two signature purple tabs and a raised rubber sole.. Buy from MATCHESFASHION.COM