206 results for vintage ankle boots
- Giorgio Armani Vintage 80s / 90s Ankle Boots Cap Toe Brown Leather Men's Sz 8Opens in a new window or tabPre-OwnedC $121.52Top Rated Seller+C $48.11 shippingfrom United States
- FLYLAND Men Fashion Vintage Chukka Leather Ankle Boots Handmade Casual LoafersOpens in a new window or tabNew (Other)C $40.95 to C $66.89Top Rated SellerFree shippingfrom China
- Men Vintage Ankle Boots Comfortable Casual Shoes Casual Boots Suitable OutdoorOpens in a new window or tabNew (Other)C $95.34Top Rated SellerWas: C $103.63 8% off+C $6.83 shippingfrom China
- Men Vintage Ankle Boots Comfortable Casual Shoes Casual Boots Suitable OutdoorOpens in a new window or tabNew (Other)C $103.17Top Rated SellerFree shippingfrom China
- New Mens Lace Up Desert Chukka Boots Oxford Dress Ankle Shoes Vintage Casual USOpens in a new window or tabNew (Other)C $50.82Was: C $54.07 6% offFree shippingfrom China
- Vintage Crockett & Jones Black Leather Derby Boots Shoes Mens UK 9 L US 10 EU 43Opens in a new window or tabPre-OwnedC $238.72Top Rated Seller1 bid · Time left17h 28m+C $48.09 shippingfrom United Kingdom
- Vintage Scarpa Brown Leather Walking Work Boots Shoes UK 9 US 10 EU 43Opens in a new window or tabPre-OwnedC $152.85Top Rated Seller0 bids · Time left3d 17hor Best Offer+C $48.09 shippingfrom United Kingdom
- Mens Ankle Cowboy Boots Premium Real Leather VintageOpens in a new window or tabBrand NewC $293.54Top Rated SellerFree shippingfrom United Kingdom
- Rare Vintage Black Leather Riding boots Shoes And Full Shoe Trees Mens UK 8 US 9Opens in a new window or tabPre-OwnedC $427.63Top Rated Seller+C $48.09 shippingfrom United Kingdom
- Bespoke Rare Vintage Henry Maxwell Brown Leather Officers boots Shoes Mens UK 8Opens in a new window or tabPre-OwnedC $2,146.76Top Rated Seller+C $48.09 shippingfrom United Kingdom
- Rare Vintage Timberland Brown Leather Green Canvas Boots Shoes Men UK 13 US 13.5Opens in a new window or tabPre-OwnedC $324.59Top Rated Seller+C $48.09 shippingfrom United Kingdom
- Bespoke Rare Vintage John Lobb Brown Leather Riding Officer boots Shoes Men UK 6Opens in a new window or tabPre-OwnedC $7,728.32Top Rated Seller+C $48.09 shippingfrom United Kingdom
- Vintage Timberland Gore-Tex Lug Sole Leather Boots Shoes Men's UK 7.5 US 8 WOpens in a new window or tabPre-OwnedC $307.42Top Rated Seller+C $48.09 shippingfrom United Kingdom
- Soft Leather Mens Boots LuxuryGenuine Leather Round Toe 2023 Black Vintage AnkleOpens in a new window or tabBrand NewC $198.08Top Rated SellerWas: C $217.68 9% off+C $27.31 shippingfrom China
- Soft Leather Mens Boots LuxuryGenuine Leather Round Toe 2023 Black Vintage AnkleOpens in a new window or tabBrand NewC $207.98Top Rated SellerWas: C $228.56 9% off+C $27.31 shippingfrom China
- Mens Boots Luxury Genuine Leather Handmade Comfortable Round Toe Vintage AnkleOpens in a new window or tabBrand NewC $187.37Top Rated SellerWas: C $205.89 9% off+C $27.31 shippingfrom China
- Men Retro Round Toe Studded PU Leather Knight Boots Zipper Low-Heel Cowboy ShoesOpens in a new window or tabBrand NewC $57.85Was: C $61.54 6% offFree shippingfrom China
- Royal Warrant Rare Vintage Peal & Co. Brown Leather Riding boots Shoes Men UK 7Opens in a new window or tabPre-OwnedC $1,286.34Top Rated Seller+C $48.09 shippingfrom United Kingdom
- Mens Military Boots Smart Casual Blinders 1920s Retro Vintage Laced AnkleOpens in a new window or tabBrand NewC $72.54Top Rated SellerFree shippingfrom United Kingdom
- Capitol Made in Canada Goat Fur Apres After Ski Men’s Boots Size 10.5 VintageOpens in a new window or tabPre-OwnedC $227.44Top Rated SellerWas: C $267.58 15% off+C $32.74 shippingfrom United States
- Mens Black Brown Slip On Ankle Boots Vintage Genuine Leather Cowboy RidingOpens in a new window or tabBrand NewC $293.54Top Rated SellerFree shippingfrom United Kingdom
- Mens Real Leather Vintage Boots Brogues 1920s Suede Tweed Laced Shoes SmartOpens in a new window or tabBrand NewC $204.79Top Rated SellerFree shippingfrom United Kingdom
- Dr. Martens England 939 Docs Leather Work Combat Mens Boots UK 11 US 12 VintageOpens in a new window or tabPre-OwnedC $220.48Top Rated SellerWas: C $259.39 15% off+C $32.52 shippingfrom United States
- Dr Docs Martens Doc Alderton Mens Lace Up Air Wair Brown Boots UK 8 US 9 VintageOpens in a new window or tabPre-OwnedC $150.84Top Rated SellerWas: C $177.47 15% off+C $57.04 shippingfrom United States
- Mens Western Cowboy Boots Vintage Pointed Knight Ankle Country Boot Riding RealOpens in a new window or tabBrand NewC $285.69Top Rated SellerFree shippingfrom United Kingdom
- Vintage Dr. Martens England 9758 Docs Leather Work Combat Mens Boots UK 11 US 12Opens in a new window or tabPre-OwnedC $220.46Top Rated SellerWas: C $259.38 15% off+C $59.09 shippingfrom United States
- Mens Round Toe Studded Leather Knight Boots Zipper Low-Heel Cowboy Shoes BEATOpens in a new window or tabNew (Other)C $44.43Was: C $47.77 7% off+C $18.20 shippingfrom China
- Vtg Dr Doc Martens 2976 Chelsea Mens Smooth Leather Black Boots Size 6 UK US 7Opens in a new window or tabPre-OwnedC $127.65Top Rated SellerWas: C $150.17 15% off+C $56.36 shippingfrom United States
- Vintage Men Boots Suede Leather Western Ankle Boots Casual Shoes SneakersOpens in a new window or tabNew (Other)C $48.14Was: C $58.71 18% offFree shippingfrom China
- Mens British Style Chelsea Lace Up Shoes Business Formal Ankle Boots Vintage HOTOpens in a new window or tabNew (Other)C $81.91Free shippingfrom China
- Mens British Vintage Pointed Toe Leather Casual Shoes High-Top Ankle Boots TrendOpens in a new window or tabNew (Other)C $94.61Top Rated SellerWas: C $105.12 10% off+C $10.91 shippingfrom China
- Mens Slim Fit Vintage Retro Sherlock Laced Smart Casual Ankle Boots LeatherOpens in a new window or tabBrand NewC $60.44Top Rated Seller+C $29.20 shippingfrom United Kingdom
- Allen Edmonds Vintage Men’s Winchester Burgundy Zip Up Ankle Boots 7.5Opens in a new window or tabPre-OwnedC $102.39Top Rated Seller0 bids · Time left1d 21hor Best Offerfrom United States
- SUBURBANS Ankle BOOTS 9.5 MEN'S Brown Suede Leather VINTAGE new Wallabee SHOESOpens in a new window or tabNew (Other)C $94.21from United States
- SUBURBANS ANKLE BOOTS, 9.5 - MENS TAN made in Spain VINTAGE leatherOpens in a new window or tabPre-OwnedC $57.65from United States
- Dr. Martens Doc England 90's Vintage Brown Lug Sole 939 Ankle Boots UK 3 US 4Opens in a new window or tabPre-OwnedC $68.17Top Rated Sellerfrom United States14 watchers
- FLYLAND Men Fashion Vintage Chukka Leather Ankle Boots Handmade Casual LoafersOpens in a new window or tabNew (Other)C $27.29 to C $54.60Top Rated SellerFree shippingfrom China
- PALLADIUM Phoenix France Vintag Men's Dark Brown Lace Up Ankle Boots Sz 43/US 10Opens in a new window or tabPre-OwnedC $95.57Top Rated Seller+C $25.94 shippingfrom UkraineFree returns
- Vintage VANS Chukka Boot Size Mens 6 Women’s 7.5 Shoes High Top Ankle Gray TBQ6Opens in a new window or tabPre-OwnedC $53.25Top Rated Sellerfrom United States
- Men Ankle Boots Chelsea Business Casual Shoes Low Heel Leather Pointed Toe YouthOpens in a new window or tabNew (Other)C $76.01Top Rated SellerWas: C $87.37 13% off+C $2.72 shippingfrom China1+ watchers
- Men's Vintage Black Ankle BOOTS All Leather 9.5 EE BuckleOpens in a new window or tabPre-OwnedC $40.89Top Rated Seller+C $72.23 shippingfrom United States12 watchers
- Dr. Martens 8287 Vintage | Original England Mens sz 10 (UK) Chunky Brown BootsOpens in a new window or tabPre-OwnedC $129.71Top Rated Sellerfrom United States
- FLYLAND Men Fashion Vintage Chukka Leather Ankle Boots Handmade Casual LoafersOpens in a new window or tabNew (Other)C $54.60 to C $66.89Top Rated SellerFree shippingfrom China
- Doc Martens Mens Sz 8 Brown Ankle Boots CK 2128 Dr Made In England 90s VintageOpens in a new window or tabPre-OwnedC $40.95+C $52.57 shippingfrom United States
- Doc Martens Mens 11 Brown Ankle Boots CK 2128 Dr Made In England 90s VintageOpens in a new window or tabPre-OwnedC $102.39Top Rated Sellerfrom United States
- Vintage IRON AGE Safety Toe Red Leather Ankle Beatle Boots Side Zip Sz 7.5 D/BOpens in a new window or tabPre-OwnedC $28.67from United States
- Dr. Martens 8287 Vintage | Original England Mens sz 11 (UK) Chunky Brown BootsOpens in a new window or tabPre-OwnedC $129.71Top Rated Sellerfrom United States
- KENNETH COLE Ankle Boots | Vintage Mid 90s | SIZE 10.5 M Black | Nice ShapeOpens in a new window or tabPre-OwnedC $27.31+C $67.05 shippingfrom United States
- FLYLAND Men Fashion Vintage Chukka Leather Ankle Boots Handmade Casual LoafersOpens in a new window or tabNew (Other)C $50.50 to C $64.16Top Rated SellerFree shippingfrom China
- 1970s CHUKKA DESERT BOOTS, NUBUCK SUEDE LEATHER, US SIZE 9, VINTAGE NEW NOS NWTOpens in a new window or tabBrand NewC $76.45Top Rated SellerWas: C $95.56 20% offfrom United States
- MIGLIORE men shoes made in Italy Olive green vintage suede lace wingtip bootOpens in a new window or tabBrand NewC $212.00Top Rated SellerFree shippingfrom Italy
- FLYLAND Men's Fashion Vintage Chukka Leather Ankle Boots Handmade Casual ShoesOpens in a new window or tabNew (Other)C $50.50 to C $64.16Top Rated SellerFree shippingfrom China
- St Johns Bay Mens Sz 8.5 Black Leather Ankle Boots Vtg Style Great Look Sz 8.5 DOpens in a new window or tabPre-OwnedC $47.77Top Rated Sellerfrom United States
- Vtg 70s Mens Sz 9 (Inside Length 10 ½") Beige Suede Chukka Moc Boots~As IsOpens in a new window or tabPre-OwnedC $20.47from United States
- Men Vintage Sears Hipster steampun MONK Buckle Ankle Boots 7.5DOpens in a new window or tabPre-OwnedC $70.98Top Rated SellerWas: C $88.73 20% offfrom United States
- Men's Clarks Stinson HI Ankle Leather Boot Dark Blue/Gray Size 10M USOpens in a new window or tabPre-OwnedC $68.25Top Rated Sellerfrom United States
- Mens Military Boots Smart Casual Blinders 1920s Retro Vintage Laced AnkleOpens in a new window or tabBrand NewC $84.99Top Rated Seller+C $29.20 shippingfrom United Kingdom
- Roper Men's Vintage Tan Ostrich Print Driving Moc Lacer Casual Shoe size 9Opens in a new window or tabNew (Other)C $81.92from United States
- Vintage BALLY Damore CHUKKA Boots Brown Leather Lace Up Made In Italy Size 11DOpens in a new window or tabPre-OwnedC $109.21from United States
- Medicus Ankle Boots Winter Shoes Lace Up Padded 80er True Vintage 80sOpens in a new window or tabPre-OwnedC $145.84Top Rated Seller+C $47.04 shippingfrom Germany
- Men's British Style Suede Casual Chelsea Ankle Boots Shoes Vintage Plus SizeOpens in a new window or tabNew (Other)C $85.02Top Rated SellerWas: C $89.50 5% off+C $13.64 shippingfrom China
- VTG Men's Black Leather Ankle Dress Boots 9 NM Madison Shoe Co. circa 1965Opens in a new window or tabPre-OwnedC $90.11Top Rated Seller+C $52.69 shippingfrom United States
- VINTAGE Dr Martens 1561 US 10 Made In England Brown Leather Oxford Shoe Low BootOpens in a new window or tabPre-OwnedC $102.40Top Rated Sellerfrom United States
- Mens Western Cowboy Boots Vintage Pointed Knight Ankle Country Boot Riding RealOpens in a new window or tabBrand NewC $231.83Top Rated Seller+C $29.20 shippingfrom United Kingdom
- Mens Vintage Leather Punk Pointy Toe Metal Chain Buckle Cowboy Rock Ankle BootsOpens in a new window or tabNew (Other)C $106.43Top Rated SellerWas: C $120.94 12% offFree shippingfrom China
- vintage black leather ankle boot J.D Fisk size 11Opens in a new window or tabPre-OwnedC $47.79from United States
- Clarks Stinson Hi Ankle Leather Chukka Style Boot Men's Size 13M #79161Opens in a new window or tabPre-OwnedC $47.79Top Rated Seller+C $67.64 shippingfrom United States
- Men Genuine Leather Shoes Soft Sole Ankle Boots Outdoor Walking Driving SneakersOpens in a new window or tabNew (Other)C $47.77 to C $62.34Free shippingfrom Hong Kong
- VTG Sears Leather Boots Mens 8D Monk Buckled Hipster fashion collectable RareOpens in a new window or tabPre-OwnedC $61.40from United States
- Men Boots Retro Comfortable British Style Shoes Formal Casual FootwearOpens in a new window or tabBrand NewC $54.11Free shippingfrom China
- Ralph Lauren Vintage Calf leather Garforth black ankle boots Mens US Size 12 EuOpens in a new window or tabBrand NewC $805.56+C $63.35 shippingfrom United States
- VINTAGE SHOE COMPANY 'VAUGHN' BLUE SUEDE BURNISHED CHUKKA BOOTS 11 M $275Opens in a new window or tabNew (Other)C $121.52Top Rated Seller+C $82.11 shippingfrom United States
- Genuine Leather Men's Winter Ankle Boots Warm Fur Snow Boots Non-slip SneakersOpens in a new window or tabNew (Other)C $60.46Was: C $73.73 18% offFree shippingfrom China
- Paul Parkman Men's Antique Brown Cap Toe Ankle BootsOpens in a new window or tabBrand NewC $955.61Free shippingfrom Turkey
- Mens Leather Shoes Driving Moccasins Casual Boat Shoes Ankle Boots LoafersOpens in a new window or tabNew (Other)C $20.03 to C $68.21Top Rated SellerWas: C $71.80 5% off+C $2.73 shippingfrom ChinaFree returns
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