Ankle Boots for Men

101 items from 10 shops found
101 items from 10 shops found
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Saint LaurentSuede Chelsea Boots - Tan
Saint Laurent  ·  Suede Chelsea Boots - Tan
USD $795.00
Delivery: USD $20.00 From Mr Porter
-30% SalomonMens Kaïpo CS WP 2 1F/-18C
Salomon  ·  Mens Kaïpo CS WP 2 1F/-18C
CAD $104.99 CAD $149.99
Delivery: free From Altitude-Sports
Dr. MartensBlack Lyme Boots
Dr. Martens  ·  Black Lyme Boots
CAD $180.00
Delivery: free From Ssense
Saint LaurentEddie Suede Chelsea Boot, Gray
Saint Laurent  ·  Eddie Suede Chelsea Boot, Gray
USD $895.00
Delivery: free From Neiman Marcus
Officine CreativeAnatomia Polished-leather Chelsea Boots - Black
Officine Creative  ·  Anatomia Polished-leather Chelsea Boots - Black
USD $226.00
Delivery: USD $20.00 From Mr Porter
LacosteMENS CROSLEY CHELSEA BOOTS
Lacoste  ·  MENS CROSLEY CHELSEA BOOTS
CAD $300.00
Delivery: Delivery costs apply From Lacoste
FryeMens Jones Chelsea - Dk Brown / 10.5 / M
Frye  ·  Mens Jones Chelsea - Dk Brown / 10.5 / M
CAD $478.00
Delivery: free From Shoeme
FryeMens Weston Leather Chelsea Boot, Black
Frye  ·  Mens Weston Leather Chelsea Boot, Black
USD $398.00
Delivery: free From Neiman Marcus
ValentinoRockstud Leather Chelsea Boot, Black
Valentino  ·  Rockstud Leather Chelsea Boot, Black
USD $1,245.00
Delivery: free From Neiman Marcus
Tod'sSuede Chelsea Boots - Dark brown
Tod's  ·  Suede Chelsea Boots - Dark brown
USD $345.00
Delivery: USD $20.00 From Mr Porter
Common ProjectsCalf Suede Chelsea Boot, Tan
Common Projects  ·  Calf Suede Chelsea Boot, Tan
USD $515.00
Delivery: Delivery costs apply From Bergdorf Goodman
ChurchsHouston Leather Chelsea Boots - Black
Churchs  ·  Houston Leather Chelsea Boots - Black
USD $580.00
Delivery: USD $20.00 From Mr Porter
Tom FordGianni Leather Chelsea Boot, Black
Tom Ford  ·  Gianni Leather Chelsea Boot, Black
USD $1,890.00
Delivery: Delivery costs apply From Bergdorf Goodman
Bottega VenetaPebbled Leather Chelsea Boot
Bottega Veneta  ·  Pebbled Leather Chelsea Boot
USD $560.00
Delivery: free From Neiman Marcus
John LobbLawry Water-resistant Burnished-leather Chelsea Boots - Dark brown
John Lobb  ·  Lawry Water-resistant Burnished-leather Chelsea Boots - Dark brown
USD $1,635.00
Delivery: USD $20.00 From Mr Porter
HudsonWatts Chelsea boot
Hudson  ·  Watts Chelsea boot
CAD $275.00
Delivery: free From Simons
SwimsMens Barry Chelsea Classic - Taupe / 11 / M
Swims  ·  Mens Barry Chelsea Classic - Taupe / 11 / M
CAD $290.00
Delivery: free From Shoeme
LanvinPebble-grain Leather Chelsea Boots - Black
Lanvin  ·  Pebble-grain Leather Chelsea Boots - Black
USD $710.00
Delivery: USD $20.00 From Mr Porter
CheaneyGodfrey Leather Chelsea Boots - Brown
Cheaney  ·  Godfrey Leather Chelsea Boots - Brown
USD $218.00
Delivery: USD $20.00 From Mr Porter
WolverineMens Alec - Black Leather / 10.5 / M
Wolverine  ·  Mens Alec - Black Leather / 10.5 / M
CAD $250.00
Delivery: free From Shoeme
Edward GreenCamden Suede Chelsea Boots - Dark gray
Edward Green  ·  Camden Suede Chelsea Boots - Dark gray
USD $1,260.00
Delivery: USD $20.00 From Mr Porter
Solid HommeLeather Chelsea Boots - Black
Solid Homme  ·  Leather Chelsea Boots - Black
USD $390.00
Delivery: USD $20.00 From Mr Porter
VinceSawyer Suede Chelsea Boot, Navy
Vince  ·  Sawyer Suede Chelsea Boot, Navy
USD $350.00
Delivery: free From Neiman Marcus
Bottega VenetaSuede Chelsea Boots - Camel
Bottega Veneta  ·  Suede Chelsea Boots - Camel
USD $730.00
Delivery: USD $20.00 From Mr Porter
Edward GreenNewmarket Grained-leather Chelsea Boots - Black
Edward Green  ·  Newmarket Grained-leather Chelsea Boots - Black
USD $1,310.00
Delivery: USD $20.00 From Mr Porter
John LobbAbbott Suede Jodhpur Boots - Brown
John Lobb  ·  Abbott Suede Jodhpur Boots - Brown
USD $1,635.00
Delivery: USD $20.00 From Mr Porter
GucciLeather Chelsea Boots - Chocolate
Gucci  ·  Leather Chelsea Boots - Chocolate
USD $845.00
Delivery: USD $20.00 From Mr Porter
Paul SmithDrummond Leather Chelsea Boots - Chocolate
Paul Smith  ·  Drummond Leather Chelsea Boots - Chocolate
USD $277.50
Delivery: USD $20.00 From Mr Porter
O KeeffeAlgy Leather Chelsea Boots - Black
O Keeffe  ·  Algy Leather Chelsea Boots - Black
USD $545.00
Delivery: USD $20.00 From Mr Porter
FolkBrandon Suede Chelsea Boots - Stone
Folk  ·  Brandon Suede Chelsea Boots - Stone
USD $305.00
Delivery: USD $20.00 From Mr Porter
FolkBrandon Suede Chelsea Boots - Black
Folk  ·  Brandon Suede Chelsea Boots - Black
USD $350.00
Delivery: USD $20.00 From Mr Porter
LanvinNubuck Chelsea Boots - Black
Lanvin  ·  Nubuck Chelsea Boots - Black
USD $615.00
Delivery: USD $20.00 From Mr Porter
Edward GreenCamden Cross-grain Leather Chelsea Boots - Black
Edward Green  ·  Camden Cross-grain Leather Chelsea Boots - Black
USD $1,260.00
Delivery: USD $20.00 From Mr Porter
Edward GreenNewmarket Suede Chelsea Boots - Brown
Edward Green  ·  Newmarket Suede Chelsea Boots - Brown
USD $1,310.00
Delivery: USD $20.00 From Mr Porter
A.P.C.Leather Chelsea Boots - Black
A.P.C.  ·  Leather Chelsea Boots - Black
USD $485.00
Delivery: USD $20.00 From Mr Porter
BerlutiPolished-leather Chelsea Boots - Dark brown
Berluti  ·  Polished-leather Chelsea Boots - Dark brown
USD $2,280.00
Delivery: USD $20.00 From Mr Porter
J.M. WestonLeather Chelsea Boots - Black
J.M. Weston  ·  Leather Chelsea Boots - Black
USD $1,070.00
Delivery: USD $20.00 From Mr Porter
Saint LaurentSuede Chelsea Boots - Black
Saint Laurent  ·  Suede Chelsea Boots - Black
USD $795.00
Delivery: USD $20.00 From Mr Porter
BalenciagaSuede Chelsea Boots - Tan
Balenciaga  ·  Suede Chelsea Boots - Tan
USD $760.00
Delivery: USD $20.00 From Mr Porter
GrensonDeclan Suede Chelsea Boots - Tan
Grenson  ·  Declan Suede Chelsea Boots - Tan
USD $356.00
Delivery: USD $20.00 From Mr Porter
Bottega VenetaSuede Chelsea Boots - Brown
Bottega Veneta  ·  Suede Chelsea Boots - Brown
USD $730.00
Delivery: USD $20.00 From Mr Porter
Saint LaurentCigar Suede Chelsea Boots - Tan
Saint Laurent  ·  Cigar Suede Chelsea Boots - Tan
USD $710.00
Delivery: USD $20.00 From Mr Porter
SantoniBurnished-suede Chelsea Boots - Charcoal
Santoni  ·  Burnished-suede Chelsea Boots - Charcoal
USD $392.50
Delivery: USD $20.00 From Mr Porter
GrensonDeclan Suede Chelsea Boots - Dark brown
Grenson  ·  Declan Suede Chelsea Boots - Dark brown
USD $355.00
Delivery: USD $20.00 From Mr Porter
FolkBrandon Suede Chelsea Boots - Tan
Folk  ·  Brandon Suede Chelsea Boots - Tan
USD $350.00
Delivery: USD $20.00 From Mr Porter
Tod'sBurnished-leather Chelsea Boots - Chocolate
Tod's  ·  Burnished-leather Chelsea Boots - Chocolate
USD $345.00
Delivery: USD $20.00 From Mr Porter
WolverineMontague Suede Chelsea Boot, Brown
Wolverine  ·  Montague Suede Chelsea Boot, Brown
USD $295.00
Delivery: free From Neiman Marcus
SwimsMens Charlie Boot - Taupe/Biscuit / 11 / M
Swims  ·  Mens Charlie Boot - Taupe/Biscuit / 11 / M
CAD $155.00
Delivery: free From Shoeme
Saint LaurentPolished-leather Chelsea Boots - Black
Saint Laurent  ·  Polished-leather Chelsea Boots - Black
USD $800.00
Delivery: USD $20.00 From Mr Porter
Officine CreativeAnatomia Suede Chelsea Boots - Anthracite
Officine Creative  ·  Anatomia Suede Chelsea Boots - Anthracite
USD $275.00
Delivery: USD $20.00 From Mr Porter
Paul SmithSearle boots
Paul Smith  ·  Searle boots
CAD $595.00
Delivery: free From Simons
John FluevogMens Holden - Grey / 10 / M
John Fluevog  ·  Mens Holden - Grey / 10 / M
CAD $425.00
Delivery: free From Shoeme
Bottega VenetaPebbled Leather Chelsea Boot
Bottega Veneta  ·  Pebbled Leather Chelsea Boot
USD $560.00
Delivery: Delivery costs apply From Bergdorf Goodman
Bottega VenetaAussie Suede Chelsea Boot, Gray
Bottega Veneta  ·  Aussie Suede Chelsea Boot, Gray
USD $820.00
Delivery: Delivery costs apply From Bergdorf Goodman
FryeWeston Suede Chelsea Boot, Chestnut
Frye  ·  Weston Suede Chelsea Boot, Chestnut
USD $398.00
Delivery: free From Neiman Marcus
J.crewKenton leather Chelsea boots
J.crew  ·  Kenton leather Chelsea boots
USD $248.00
Delivery: free From J.CREW
Common ProjectsSaffiano Leather Chelsea Boots - Black
Common Projects  ·  Saffiano Leather Chelsea Boots - Black
USD $507.30
Delivery: USD $20.00 From Mr Porter
John FluevogMens Holden - Green / 10 / M
John Fluevog  ·  Mens Holden - Green / 10 / M
CAD $425.00
Delivery: free From Shoeme
BurberryPearsley Washed Suede Chelsea Boots, Brown
Burberry  ·  Pearsley Washed Suede Chelsea Boots, Brown
USD $595.00
Delivery: free From Neiman Marcus
PradaCalf Leather Chelsea Boot, Black
Prada  ·  Calf Leather Chelsea Boot, Black
USD $850.00
Delivery: free From Neiman Marcus
PradaSaffiano Leather Chelsea Boot, Black
Prada  ·  Saffiano Leather Chelsea Boot, Black
USD $820.00
Delivery: free From Neiman Marcus
GucciStrand Hammered Leather Chelsea Boot w/Web, Navy
Gucci  ·  Strand Hammered Leather Chelsea Boot w/Web, Navy
USD $975.00
Delivery: free From Neiman Marcus
Tom FordGianni Leather Chelsea Boot, Black
Tom Ford  ·  Gianni Leather Chelsea Boot, Black
USD $1,890.00
Delivery: free From Neiman Marcus
PradaLeather Chelsea Rubber-Bottom Boot, Brown
Prada  ·  Leather Chelsea Rubber-Bottom Boot, Brown
USD $720.00
Delivery: free From Neiman Marcus
PradaRunway Leather Chelsea Boot, Black
Prada  ·  Runway Leather Chelsea Boot, Black
USD $720.00
Delivery: free From Neiman Marcus
TimberlandMens Adventure 2.0 Cupsole Chelsea - Dark Brown Full-grain / 10.5 / M
Timberland  ·  Mens Adventure 2.0 Cupsole Chelsea - Dark Brown Full-grain / 10.5 / M
CAD $150.00
Delivery: free From Shoeme
Salvatore FerragamoGiotto Polished Calfskin Chelsea Boot, Dark Brown
Salvatore Ferragamo  ·  Giotto Polished Calfskin Chelsea Boot, Dark Brown
USD $895.00
Delivery: Delivery costs apply From Bergdorf Goodman
Cole HaanWarren Waterproof Leather Chelsea Boot, Black
Cole Haan  ·  Warren Waterproof Leather Chelsea Boot, Black
USD $250.00
Delivery: free From Neiman Marcus
Saint LaurentWyatt 40mm Mens Metallic Leather Ankle Boot, Gold
Saint Laurent  ·  Wyatt 40mm Mens Metallic Leather Ankle Boot, Gold
USD $995.00
Delivery: Delivery costs apply From Bergdorf Goodman
RepresentEspresso suede Chelsea boot
Represent  ·  Espresso suede Chelsea boot
CAD $425.00
Delivery: free From Simons
Tom FordGianni Leather Chelsea Boot, Brown
Tom Ford  ·  Gianni Leather Chelsea Boot, Brown
USD $1,990.00
Delivery: Delivery costs apply From Bergdorf Goodman
GucciStrand Hammered Leather Chelsea Boot w/Web, Navy
Gucci  ·  Strand Hammered Leather Chelsea Boot w/Web, Navy
USD $975.00
Delivery: Delivery costs apply From Bergdorf Goodman
Common ProjectsChelsea Boots for Men, Black, Leather, 2016, 7.5 9
Common Projects  ·  Chelsea Boots for Men, Black, Leather, 2016, 7.5 9
CAD $708.00
Delivery: CAD $9.90 From Raffaello Network
PradaCalf Leather Chelsea Boot, Black
Prada  ·  Calf Leather Chelsea Boot, Black
USD $850.00
Delivery: Delivery costs apply From Bergdorf Goodman
HudsonTonti chelsea boot
Hudson  ·  Tonti chelsea boot
CAD $230.00
Delivery: free From Simons
Red Wing ShoesMens Beckman Round 9016 - Cigar Featherstone / 10.5 / D (Medium)
Red Wing Shoes  ·  Mens Beckman Round 9016 - Cigar Featherstone / 10.5 / D (Medium)
CAD $400.00
Delivery: free From Shoeme
Thom BrowneGrained Leather Chelsea Boot, Black
Thom Browne  ·  Grained Leather Chelsea Boot, Black
USD $1,250.00
Delivery: Delivery costs apply From Bergdorf Goodman
Paul SmithBrown Suede Marlowe Chelsea Boots
Paul Smith  ·  Brown Suede Marlowe Chelsea Boots
CAD $495.00
Delivery: free From Ssense
J.crewKenton suede Chelsea boots
J.crew  ·  Kenton suede Chelsea boots
USD $228.00
Delivery: free From J.CREW
Paul SmithBrown Suede Gerald Chelsea Boots
Paul Smith  ·  Brown Suede Gerald Chelsea Boots
CAD $450.00
Delivery: free From Ssense
GuidiBlack Suede Chelsea Boots
Guidi  ·  Black Suede Chelsea Boots
CAD $1,375.00
Delivery: free From Ssense
Paul SmithBlack Gerald Chelsea Boots
Paul Smith  ·  Black Gerald Chelsea Boots
CAD $450.00
Delivery: free From Ssense
HudsonBlack Watts Chelsea Boots
Hudson  ·  Black Watts Chelsea Boots
CAD $290.00
Delivery: free From Ssense
Saint LaurentTan Suede Wyatt Chelsea Boots
Saint Laurent  ·  Tan Suede Wyatt Chelsea Boots
CAD $1,165.00
Delivery: free From Ssense
MarsèllBeige Zucca Media Chelsea Boots
Marsèll  ·  Beige Zucca Media Chelsea Boots
CAD $1,130.00
Delivery: free From Ssense
HudsonTan Suede Tamper Chelsea Boots
Hudson  ·  Tan Suede Tamper Chelsea Boots
CAD $235.00
Delivery: free From Ssense
Neil BarrettBlack Zip Chelsea Boots
Neil Barrett  ·  Black Zip Chelsea Boots
CAD $670.00
Delivery: free From Ssense
BurberryBlack Davy Mod Chelsea Boots
Burberry  ·  Black Davy Mod Chelsea Boots
CAD $995.00
Delivery: free From Ssense
Thom BrowneBlack Chelsea Boots
Thom Browne  ·  Black Chelsea Boots
CAD $1,470.00
Delivery: free From Ssense
LanvinBlack Nubuck Chelsea Boots
Lanvin  ·  Black Nubuck Chelsea Boots
CAD $895.00
Delivery: free From Ssense
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The Best Ankle Boot-Bottom Pairings

Some pairs are a match made in wardrobe heaven. Cooler than jeans and a tee, and more casual than a suit and tie, we deem the following ankle boot, trouser combos the best of any and all fashion pairings.

Jeans

No matter if they’re dark washed and straight-legged or bright white and skinny, team your favorite denim with a killer ankle boot to match.

Why: From the rowdy and rebellious to the prim and proper, the best of the stylish best have donned denim perfection with their favorite footwear. We think it’s time you paired the beloved bottom with ankle boots that are just as cool.

How: Find a cut and color that fit your style best. Are you clean cut and casual? If so, find comfort in a pair dark blue, slim fit jeans and a suede ankle boot. Looking to don something a bit more daring? Roll the hems of an inky black skinny and style the bottoms with studded, leather ankle boots.

Cropped Trousers

Hitting just at your ankle and floating casually above the neck of your boot, there’s something so polished and proper about a perfectly cropped trouser and ankle boot combo.

Why: The clean cut of a cropped pant offers a playful juxtaposition against the edgier appearance of an ankle boot.

How: Turn up the contrast and team a cool colored cropped trouser in blue, olive or burnt orange with a sinister, black ankle boot. Go for texture and find a boot made of lush velvet or buttery leather.

Suits

Bring a cool kid look to your suits with the help of a bad boy ankle boot.

Why: Unleash your inner rocker and get noticed by HR for all of the right reasons. The boot works as an unconventional office-appropriate option that brings more personality to your corporatewear than those loafers ever could.

How: Keep things neutral and pair a matte black ankle boot with a bespoke, gray suit. Not only will the monochrome look play in your favor, you’ll also be able to get the most wear out of a black shoe.

Challenge monogamy and pair your ankle boots with any of these three bottoms for a dapper look that can’t be beat.

Finding your ankle boots' perfect match starts with finding the perfect ankle boot.

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Tamlin (Mens) - Black
Serberhus D-Anklyx (Mens) - Tawny Red
Vibo (Mens) - Black Hornback/Ostrich
Just Us (Mens) - Tan/Cognac Suede/Leather
Haven (Mens) - Petrol/White/Dark Cymbal Suede
Charlton (Mens) - Black/Navy Crazy Horse
Siped Outsole Performance Ankle Boot (Brown) Mens Boots
Genuine Snake 15549 (Mens) - Black
GR500 High Romeo (Mens) - Soggy Brown
Watershed Waterproof (Mens) - Bitteroot Full Grain Leather
Bristol Side Zip Ankle Boot (Black) Mens Boots
Realm Pull (Mens) - Black
Serberhus D-Kallien (Mens) - Tawny Red
Serberhus D-Anklyx (Mens) - Black
Tyler Lace Up (Black Soft Vintage Leather) Womens Lace-up Boots
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