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Chelsea Boots for Men

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chelsea boots in brown faux leather with black sole

Asos Design

chelsea boots in brown faux leather with black sole

$43

At Asos.com

Boots by ASOS DESIGN That 'new shoe' feeling Pull tab for easy entry Slip-on style Elasticated inserts Slim toe Stacked sole Textured tread. Buy from ASOS.com
Waffle Chunky-sole Leather Chelsea Boots - Mens - Black

Primury

Waffle Chunky-sole Leather Chelsea Boots - Mens - Black

$216

At Matchesfashion.com

Primury - London-based label Primury puts a fresh spin on the traditional Chelsea boot silhouette with this chunky-soled Waffle pair - named after the ridged panel around the heel. They're made in Portugal from responsibly sourced leather and part-recycled rubber, then feature large elasticated panels on the sides and pull-on tabs.. Buy from MATCHESFASHION.COM
chelsea boots in gray faux suede

Asos Design

chelsea boots in gray faux suede

$40

At Asos.com

Boots by ASOS DESIGN For your daytime thing Slip-on style Elasticated inserts Pull tab Slim toe Moulded tread. Buy from ASOS.com
Marcel boots

Apc

Marcel boots

$580 $416

At 24s

Collection of textures Visible stitching High tongue Tone-on-tone lacing Thick, notched sole. Buy from 24S
Wyatt Leather Chelsea Boots - Mens - Black

Saint Laurent

Wyatt Leather Chelsea Boots - Mens - Black

$895

At Matchesfashion.com

Saint Laurent - Saint Laurent's black Wyatt Chelsea boots rest on a slightly slanted stacked heel that brings a rock and roll edge to the sartorial silhouette, which is named after its popularity in the London borough in the 1960s. They're made from smooth leather with a squared-off point toe and traditional elasticated side gussets.. Buy from MATCHESFASHION.COM
Clarks Clarkdale Gobi Chelsea Boot

Clarksr

Clarks Clarkdale Gobi Chelsea Boot

$170

At Nordstrom

Breathable, lightweight materials define a water-resistant Chelsea boot featuring OrthoLite arch support for all-day comfort. Style Name: Clarks Clarkdale Gobi Chelsea Boot (Men). Style Number: 5685179 2.. Buy from Nordstrom
Dr. Scholl's Levine Side Zip Chelsea Boot at Nordstrom Rack

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
Wyatt Suede Chelsea Boots - Mens - Black

Saint Laurent

Wyatt Suede Chelsea Boots - Mens - Black

$895

At Matchesfashion.com

Saint Laurent - Chelsea boots are synonymous with the swinging sixties and Saint Laurent's black Wyatt pair is an ode to the house's rock 'n' roll heritage. They're made in Italy from soft suede with a squared-off point toe, elasticated side gussets and a small slightly slanted stacked heel.. Buy from MATCHESFASHION.COM
Wide Fit heeled chelsea boots with pointed toe in leopard print-Brown

Asos Design

Wide Fit heeled chelsea boots with pointed toe in leopard print-Brown

$93

At Asos.com

Boots by ASOS DESIGN Two reasons to add to cart All-over leopard print Zip-side fastening Pointed toe Block heel Wide fit. Buy from ASOS.com
Ankle Boot In Leather And Brown Color

Santoni

Ankle Boot In Leather And Brown Color

$598 $319

At Italist

Leather ankle boot brown color smooth upper side zip closure side buckle inner lining in leather rubber sole made in italy. Buy from Italist
Tire Waved-sole Leather Boots - Mens - White Black

Bottega Veneta

Tire Waved-sole Leather Boots - Mens - White Black

$1,150

At Matchesfashion.com

Bottega Veneta - Creative director Daniel Lee's graphic vision for Bottega Veneta is reflected by the undulating, waved black rubber midsole of these white Tire boots, which extends around the upper. They're crafted in Italy from leather with elongated elasticated side panels and finished with pull tabs at the front and back.. Buy from MATCHESFASHION.COM
Wide Fit heeled chelsea boots with pointed toe in black leather with black sole

Asos Design

Wide Fit heeled chelsea boots with pointed toe in black leather with black sole

$93

At Asos.com

Boots by ASOS DESIGN Two reasons to add to cart Zip-side fastening Pointed toe Block heel Wide fit. Buy from ASOS.com
NUNN BUSH Fuse Leather Plain Toe Chelsea Boot - Wide Width Available at Nordstrom Rack

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
Beetle Crackled-leather Chelsea Boots - Mens - Black

Rick Owens Drkshdw

Beetle Crackled-leather Chelsea Boots - Mens - Black

$790

At Matchesfashion.com

Rick Owens DRKSHDW - Capture Rick Owens DRKSHDW's dystopian aesthetic with these black Beetle Chelsea boots, which are crafted from textural crackled leather. Made in Italy, they have a chunky platform sole and a pull loop at the elasticated topline.. Buy from MATCHESFASHION.COM
heeled chelsea boots with rounded toe in black leather with black sole

Asos Design

heeled chelsea boots with rounded toe in black leather with black sole

$60

At Asos.com

Boots by ASOS DESIGN Two reasons to add to cart Zip-side fastening Round toe Block heel. Buy from ASOS.com
Ankle Boot In Leather And Black Color

Santoni

Ankle Boot In Leather And Black Color

$598 $319

At Italist

Leather ankle boot brown color smooth upper side zip closure side buckle inner lining in leather composition 100% calf leather rubber sole made in italy. Buy from Italist
2976 Leather Chelsea Boots - Mens - Burgundy

Dr. Martens

2976 Leather Chelsea Boots - Mens - Burgundy

$205

At Matchesfashion.com

Dr. Martens - Dr. Martens' burgundy 2976 Chelsea boots are modelled on the British label's original silhouette from the early 1970s. They're crafted in the UK from smooth leather featuring yellow topstitching, then finished with a jacquard heel tab, elasticated side gussets and the signature Goodyear-welt rubber sole.. Buy from MATCHESFASHION.COM
seymour chelsea boots in charcoal suede-Gray

Base London

seymour chelsea boots in charcoal suede-Gray

$119

At Asos.com

Boots by Base London That 'new shoe' feeling Mid-cut design Pull-on style Pull tabs for easy entry Elasticated inserts Round toe Slim sole. Buy from ASOS.com
Eastland Justin Leather Chelsea Boot at Nordstrom Rack

Hautelook, A Nordstrom Company

Eastland Justin Leather Chelsea Boot at Nordstrom Rack

$125 $60

At Hautelook

Sizing: True to size. D=standard width. Round toe. Leather with contrasting textile construction. Dual elasticated side gore panels. Pull-on style. Front and back pull-tabs. Padded footbed. Approx. 5.5" shaft height, 11" opening circumference. Grip sole. Imported. Buy from Hautelook
Kyra Web-stripe Leather Chelsea Boots - Mens - Black

Gucci

Kyra Web-stripe Leather Chelsea Boots - Mens - Black

$950

At Matchesfashion.com

Gucci - Gucci pays homage to its equestrian inspirations with these black Kyra Chelsea boots. They're crafted in Italy from leather with a green and red Web-stripe grosgrain heel tab - a signature based on vintage saddles - then set on a practical rubber tread sole.. Buy from MATCHESFASHION.COM
leather chelsea boots in brown

Jack & Jones

leather chelsea boots in brown

$86

At Asos.com

Boots by Jack & Jones Your new favorite boots Pull tab for easy entry Elasticated inserts Almond toe Flat sole. Buy from ASOS.com
2001-2 HIGH boots

Raf Simons

2001-2 HIGH boots

$650 $260

At 24s

Raf Simons designed and signed these boots with a rounded toe and a streamlined look. These high-top boots combine a small, stylish heel and a zip fastening on the back.. Buy from 24S
Marco Leather Chelsea Boots - Mens - Black

Grenson

Marco Leather Chelsea Boots - Mens - Black

$325

At Matchesfashion.com

Grenson - Grenson's black Marco Chelsea boots are reminiscent of styles worn by members of the Mod subculture in 1960s London. They're meticulously shaped from polished leather with an almond toe and set on a dramatically stacked Cuban heel.. Buy from MATCHESFASHION.COM
Laguna Chelsea Boot Sesame Leather

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
Woven-leather Combat Boots - Mens - Black

Givenchy

Woven-leather Combat Boots - Mens - Black

$1,195

At Matchesfashion.com

Givenchy - Givenchy's artisanal heritage is captured through these black combat boots, characterised by an intricately woven upper. They're crafted in Italy from polished leather to a high-top silhouette that is hallmarked at the cuff using logo-debossed tabs, then finished with a hard-wearing rubber tread sole. Wear them with a warming sweater and cargo trousers to capture the house's utilitarian aesthetic.. Buy from MATCHESFASHION.COM
Born Pike Leather Chelsea Boot at Nordstrom Rack

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
Vintage 2976 Leather Chelsea Boots - Mens - Black

Dr. Martens

Vintage 2976 Leather Chelsea Boots - Mens - Black

$205

At Matchesfashion.com

Dr. Martens - Dr. Martens first put its rock and roll spin on the Chelsea boot - which dates to 1851 - in the 1970s and this black Vintage 2976 style is an exact replica of the label's first design. They're made in the original Northamptonshire factory from soft leather with elasticated side gussets, the signature AirWair heel pulls and Goodyear-welt rubber sole, framed with hallmark yellow stitching.. Buy from MATCHESFASHION.COM
Spazzolato leather high boots

Dries Van Noten

Spazzolato leather high boots

$1,015 $507

At 24s

Contrast stitching Zipper closure Stacked heel Thick notched sole. Buy from 24S
Exaggerated-sole Leather Chelsea Boots - Mens - Black

Jil Sander

Exaggerated-sole Leather Chelsea Boots - Mens - Black

$620

At Matchesfashion.com

Jil Sander - Jil Sander offers a textured iteration of the classic Chelsea boot with this black pair constructed with ribbed rubber panels and an exaggerated sole. They're made in Spain from soft leather with ankle pulls and an elasticated gusset that's accentuated with raw edges. Slip them on with structured staples for a sophisticated look.. Buy from MATCHESFASHION.COM
Wide Fit chelsea boots in brown

Asos Design

Wide Fit chelsea boots in brown

$43

At Asos.com

Boots by ASOS DESIGN That 'new shoe' feeling Pull tab for easy entry Slip-on style Elasticated inserts Slim toe Stacked sole Textured tread Wide fit. Buy from ASOS.com
Beetle Bozo Tractor Leather Chelsea Boots - Mens - Black

Rick Owens

Beetle Bozo Tractor Leather Chelsea Boots - Mens - Black

$1,075

At Matchesfashion.com

Rick Owens - Rick Owens considers geometry to create the angular elasticated side panels of these black Beetle Bozo Tractor Chelsea boots, resulting in a nonchalant look. They're crafted in Italy from grained leather with a heel tab and are set on a chunky rubber sole.. Buy from MATCHESFASHION.COM
Karl Lagerfeld Paris Side Zip Chelsea Boot at Nordstrom Rack

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
Albie Leather Chelsea Boots - Mens - Black

Grenson

Albie Leather Chelsea Boots - Mens - Black

$379

At Matchesfashion.com

Grenson - Grenson's black Albie boots are a lengthened version of the traditional Chelsea boot. They're made from smooth leather with a narrow side gusset that's elasticated so they can be slipped into comfortably, and set on augmented tread soles designed for assured traction and durability.. Buy from MATCHESFASHION.COM
Ankle Boots

Car Shoe

Ankle Boots

$384 $280

At Italist

man ankle boots, elastic closure, back logoComposition: 100% Calf Leather/ Rubber Sole. Buy from Italist
Tabi Split-toe Leather Chelsea Boots - Mens - Black

Maison Margiela

Tabi Split-toe Leather Chelsea Boots - Mens - Black

$1,010

At Matchesfashion.com

Maison Margiela - Maison Margiela's black Tabi Chelsea boots were unveiled on the house's debut Spring/Summer 1989 runway, defined by a split toe inspired by traditional socks worn with thonged sandals in 15th century Japan. They're crafted in Italy from smooth leather with a signature white stitch at the heel - a recurring feature that hallmarks the house's collections. Wear them to disrupt tailored separates.. Buy from MATCHESFASHION.COM
Ankle Boot Men's Shoes

Minnetonka

Ankle Boot Men's Shoes

$75

At Macy's

The collar on this versatile slipper can be rolled up or down, depending on the level of desired warmth. The Minnetonka Ankle Boot slippers have a soft lining making them the perfect gift.. Buy from Macy's
Wyatt Leather Chelsea Boots - Mens - Dark Brown

Saint Laurent

Wyatt Leather Chelsea Boots - Mens - Dark Brown

$975

At Matchesfashion.com

Saint Laurent - Saint Laurent's brown Wyatt Chelsea boots are a modern update on a classic silhouette that was first invented in 1851 by Queen Victoria's royal cordwainer J. Sparkes-Hall. They're made in Italy from smooth leather with an almond toe and elasticated side panels, then set on a small stacked heel.. Buy from MATCHESFASHION.COM
Frye Peyton Chelsea Boot at Nordstrom Rack

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
The Tire Leather Chelsea Boots - Mens - Black

Bottega Veneta

The Tire Leather Chelsea Boots - Mens - Black

$1,100

At Matchesfashion.com

Bottega Veneta - Bottega Veneta's black The Tire boots are a contemporary reimagining of the classic Chelsea boot. They're made in Italy with an elasticated gusset and rounded toe, then set atop a rubber midsole with waved top edge and a chunky tread sole.. Buy from MATCHESFASHION.COM
Lace-up Leather Boots

Dolce & Gabbana

Lace-up Leather Boots

$1,001 $616

At Italist

Ankle boot Brown Textured leather Closure with laces Round tip Leather lining Textured rubber soleComposition: 100% Calf. Buy from Italist
seymour chelsea boots in brown leather

Base London

seymour chelsea boots in brown leather

$119

At Asos.com

Boots by Base London Two reasons to add to cart Pull tab for easy entry Elasticated inserts Round toe Moulded tread. Buy from ASOS.com
Waffle Chunky-sole Leather Chelsea Boots - Mens - White/ivory

Primury

Waffle Chunky-sole Leather Chelsea Boots - Mens - White/ivory

$216

At Matchesfashion.com

Primury - Primury puts a directional spin on the traditional Chelsea boot silhouette with this minimalist white Waffle pair. They're crafted in Portugal with a responsibly sourced leather upper and a part-recycled rubber chunky role, then are accented by pull-on tabs at the high ankles.. Buy from MATCHESFASHION.COM
Karl Lagerfeld Paris Side Zip Chelsea Boot at Nordstrom Rack

Hautelook, A Nordstrom Company

Karl Lagerfeld Paris Side Zip Chelsea Boot at Nordstrom Rack

$350 $150

At Hautelook

An elastic side gore and a side zip entry allow for ease of fit and movement in this burnished leather Chelsea boot.Sizing: True to size. Square burnished toe. Side elastic side gore. Side zip closure. Cushioned insole. Imported. Buy from Hautelook
Warren Suede Chelsea Boots - Mens - Light Brown

Grenson

Warren Suede Chelsea Boots - Mens - Light Brown

$314

At Matchesfashion.com

Grenson - Grenson's beige Warren boots are shaped to a classic Chelsea silhouette, a style that was first invented by Queen Victoria's shoemaker J. Sparkes-Hall in the 19th century. They're crafted from suede with elasticated side panels, then set on a robust leather midsole and anti-slip rubber sole.. Buy from MATCHESFASHION.COM
heeled chelsea boots with rounded toe in white leather with white sole

Asos Design

heeled chelsea boots with rounded toe in white leather with white sole

$107

At Asos.com

Boots by ASOS DESIGN Two reasons to add to cart Zip-side fastening Round toe Block heel. Buy from ASOS.com
Grained leather chelsea boots

Dries Van Noten

Grained leather chelsea boots

$890 $534

At 24s

Chelsea ankle boots Visible stitching Grained leather Thick outer sole Rounded heel. Buy from 24S
stacked heel western chelsea boot in black leather with angular sole

Asos Design

stacked heel western chelsea boot in black leather with angular sole

$82

At Asos.com

Boots by ASOS DESIGN The perfect boots don't exi- Zip-side fastening Pointed toe Angular heel. Buy from ASOS.com
NUNN BUSH Fuse Leather Plain Toe Chelsea Boot - Wide Width Available at Nordstrom Rack

Hautelook, A Nordstrom Company

NUNN BUSH Fuse Leather Plain Toe Chelsea Boot - Wide Width Available at Nordstrom Rack

$100 $70

At Hautelook

A leather Chelsea boot featuring memory foam cushioning and a grip sole delivers polished style with everyday comfort. Sizing: True to size. M=standard width, W=wide width. Plain toe. Leather and textile upper. Side inset elastic gores. Pull-on style. Reinforced heel counter with pull tab. Comfort gel memory foam cushioning. Goodyear welt. Low block heel. Grip sole. Imported. Buy from Hautelook