120,000+ results for men's ankle casual shoes
- Men's Chelsea Ankle Boots Classic Dress Casual Elastic Slip On ShoesOpens in a new window or tabBrand New$37.99Was: $54.27 30% offFree shipping67+ sold
- Men's Ankle Boots Handmade Outdoor Casual Shoes Non-slip High-top Hiking ShoesOpens in a new window or tabNew (Other)$40.89 to $47.00Free shippingfrom China
- Pikolinos Men's Shoes Size 10 EU 43 Soft Leather Casual Lace Up Ankle BootsOpens in a new window or tabPre-Owned$31.36Top Rated Plus+$15.45 shippingFree returns
- New Fashion Men's Ankle Boots Casual Shoes Athletic Running Sneakers Walking GymOpens in a new window or tabNew (Other)$10.44 to $35.14Was: $36.99 5% offFree shippingfrom ChinaFree returns
- Men's Suede Leather Chukka Boots Lace Up Oxfords Dress Casual Shoes Ankle ShoesOpens in a new window or tabBrand New$21.79Was: $25.64 15% offFree shippingBuy 1, get 1 9% off with coupon
- Men's Chelsea Ankle Boots Slip On Suede Leather Chukka Dress Boots Size 6.5-15Opens in a new window or tabBrand New$39.79Was: $44.21 10% offFree shippingExtra 6% off with coupon
- Men's Timberland 6 In. Premium Boot WheatOpens in a new window or tabBrand New$159.95Top Rated PlusFree shippingFree returns
- Men Sneakers Casual Shoes High Winter Warm Loafers Luxury Lace Up Ankle BootsOpens in a new window or tabBrand New$21.99 to $39.99Free shippingFree returns
Picked For You
Sponsored | Top selling items from highly rated sellers with free shipping- Men's Chelsea Ankle Boots Slip On Oxford Boots Shoes Size 6.5-15Opens in a new window or tabBrand New$33.52Was: $35.28 5% offFree shipping
- Men's Fashion Breathable Ankle Boots Comfortable Outdoor High Top Casual ShoesOpens in a new window or tabNew (Other)$31.16 to $45.10Was: $38.00 18% offFree shippingfrom China
- Dark Blue Premium Non-Slip Mens Ankle Outdoor Boots Casual and Breathable-Size 9Opens in a new window or tabNew (Other)$11.68Free shippingfrom ChinaLast one
- Genuine Leather Ankle Boots Men's Casual Shoes Handmade Fashion Loafers SneakersOpens in a new window or tabNew (Other)$26.99 to $29.99Free shippingfrom China
- Men's Chukka Boots Lace Up Dress Water-Resistant Shoes Ankle Boots Size 6.5-13Opens in a new window or tabBrand New$33.24Was: $34.99 5% offFree shipping
- Amali Mens Casual Low Top Chukka Boots Designer Lace Up Suede Moc Toe Ankle ShoeOpens in a new window or tabBrand New$49.99 to $59.99Free shipping
- NORTIV 8 Men's Military Tactical Boots Motorcycle Combat Ankle High Work ShoesOpens in a new window or tabBrand New$63.94Was: $79.93 20% offFree shippingExtra 25% off with coupon
- Men's British Chelsea Casual Ankle Boots Soft Leather Zip Heels Pointy Toe ShoesOpens in a new window or tabNew (Other)$45.07Was: $50.08 10% off+$14.99 shippingfrom China
- Alpine Swiss Mens Ankle Boots Dressy Casual Leather Lined Dress Shoes Lace up NWOpens in a new window or tabBrand New$39.99List price: $95.00 58% offFree shipping
- TIMBERLAND WATERPROOF MEN'S SIZE 8.5 M SLIP ON LEATHER 1/2 BOOT SHOEOpens in a new window or tabPre-Owned$39.00+$11.40 shipping
- Men's Dress Oxford Boots Lace up Busines Leather Chukka Ankle ShoesOpens in a new window or tabBrand New$35.99Was: $51.41 30% offFree shippingExtra 7% off with coupon
- Chukka Boots Black Suede Ankle Boots Lace Up Leather Casual Shoe Men's 12Opens in a new window or tabNew (Other)$43.95+$12.45 shipping
- Men's Suede Leather Chukka Desert Boots Ankle Bootie Lace Up Dress Oxfords ShoesOpens in a new window or tabBrand New$21.89Was: $27.36 20% offFree shipping6+ watchers
- Day Five Mens Casual Zip Up Chelsea Boot ShoesOpens in a new window or tabBrand New$21.99List price: $69.99 69% off+$4.99 shipping17+ watchers
- Men's High Quality Casual Shoes Sneakers Walking Shoes Comfortable Ankle BootsOpens in a new window or tabNew (Other)$37.00 to $40.00Free shippingfrom China
- Men's Chukka Boots Suede Leather Lace Up Desert Oxford Chelsea ShoesOpens in a new window or tabBrand New$36.99Was: $52.84 30% offFree shippingExtra 7% off with coupon
- Blackstone Chukka Nordic Blue Leather Ankle Boots Mens Size US 10 EU 44Opens in a new window or tabPre-Owned$59.95+$9.99 shippingFree returns
- New Luxury Men Rivets Spikes Ankle Boots Casual Fashion High Top Sneakers ShoesOpens in a new window or tabNew (Other)$84.90Was: $106.13 20% offFree shippingfrom China2+ watchers
- Men's Leather Chukka Boots Casual Boots Stylish Business Dress BootsOpens in a new window or tabBrand New$33.99Was: $48.56 30% offFree shipping24+ watchers
- Brand New Men's Steel Toe Work Boots 6" Black Leather Oil Resistant Ankle ShoesOpens in a new window or tabBrand New$25.10 to $33.20Was: $32.89 10% off+$15.99 shippingFree returnsSave up to 5% when you buy more
- Men's Waterproof Ankle Boots Climbing Hiking Outdoor Work Shoes High Top LeatherOpens in a new window or tabNew (Other)$54.95Free shippingfrom China
- GoldToe Men's Black Cotton Ankle Athletic Sock, 6 Pair Shoe Size 6-12.5Opens in a new window or tabNew (Other)$13.97Free shippingSave up to 10% when you buy more
- Men's Pointed Toe Chelsea Boots British Suede Casual Ankle Shoes Dress FormalOpens in a new window or tabBrand New$46.49Was: $49.99 7% offFree shippingfrom China
- Men's Boots High Top PU Leather Ankle Casual Outdoor Lace Up Comfort ShoesOpens in a new window or tabNew (Other)$49.25Was: $55.34 11% off+$5.99 shippingfrom China
- Dockers Boots Men Size 8.5M Footwear Rawls Ankle Side Zip ShoesOpens in a new window or tabNew (Other)$59.00Free shipping
- Worn Once. IMMACULATE Sz 11 Brown Faux Suede Ankle Shoe By Goodfellow.Opens in a new window or tabPre-Owned$13.00+$11.10 shipping
- Crocs Men's and Women's Shoes - Baya Clogs, Slip On Shoes, Waterproof SandalsOpens in a new window or tabBrand New$34.99List price: $50.00 30% offFree shippingFree returns30% off $100+
- Lugz Pine Ridge Water Resistant MPINERV-649 Mens Brown Casual Dress Boots 7Opens in a new window or tabBrand New$16.99Top Rated PlusList price: $80.00 79% offFree shippingFree returns3 watchers
- Lugz Range MRANGD-001 Mens Black Nubuck Lace Up Casual Dress Boots 8Opens in a new window or tabBrand New$19.99Top Rated PlusList price: $80.00 75% offFree shippingFree returns25 watchers
- Crocs Men's and Women's Shoes - Bayaband Clogs, Slip On Water ShoesOpens in a new window or tabBrand New$39.99List price: $65.00 38% offFree shippingFree returns30% off $100+
- Indestructible Waterproof Shoe Men's Safety Shoes Composite Toe Shoes Work BootsOpens in a new window or tabNew (Other)$26.99 to $41.39Was: $45.99 10% offFree shippingSave up to 8% when you buy more
- Mens Leather Sports Shoes Comfort Walking Sneakers Casual Soft Ankle Boots SizeOpens in a new window or tabNew (Other)$10.35 to $34.68Was: $36.50 5% offFree shippingfrom ChinaFree returns1+ watchers
- Men Sneakers Casual Shoes High Winter Warm Loafers Luxury Lace Up Ankle BootsOpens in a new window or tabBrand New$29.99Free shippingfrom China
- Cestfini Men's Chukka Boots Casual Leather Dress AnkleOpens in a new window or tabBrand New$39.99 to $70.99Free shippingFree returns
- Rockport Total Motion Lite Zip Chukka CI5721 Mens Brown Leather Chukkas BootsOpens in a new window or tabBrand New$30.99Top Rated PlusList price: $120.00 74% offFree shippingFree returns
- Men Knit Sock Black n White Trainer Fashion Sneaker Casual Shoes Ankle Boots BOWOpens in a new window or tabBrand New$25.15Was: $27.64 9% off+$9.99 shippingfrom China
- Men's Casual Shoes High Top Sneakers Ankle Boots Lace Up Warm Walking ShoesOpens in a new window or tabNew (Other)$31.92 to $40.32Was: $48.00 16% offFree shippingfrom China
- English Laundry Ardley EL2472B Mens Black Leather Casual Dress BootsOpens in a new window or tabBrand New$54.99Top Rated PlusList price: $210.00 74% offFree shippingFree returns
- Dockers Footwear Men's Ankle BootOpens in a new window or tabBrand New$65.99 to $67.99Free shippingFree returns
- US Men's Leather Chukka Boots Casual Boots Stylish Business Dress BootsOpens in a new window or tabBrand New$33.89Was: $45.19 25% offFree shipping
- Lugz Fringe MFRGD-4320 Mens Blue Synthetic Lace Up Ankle BootsOpens in a new window or tabBrand New$47.99Top Rated PlusList price: $70.00 31% offFree shippingFree returnsExtra 15% off with coupon
- Lugz Nile HI MNILEHV-0761 Mens Black Synthetic Lace Up Casual Dress BootsOpens in a new window or tabBrand New$25.99Top Rated PlusList price: $75.00 65% offFree shippingFree returns7+ watchers
- Weatherproof Men's Cold Weather Lined Sneaker Boot Shoes, Logjam, Brown, Size 12Opens in a new window or tabBrand New$19.97Top Rated Plus+$10.00 shippingFree returns
- Clarks Desert Coal 26169997 Mens Blue Suede Lace Up Chukkas BootsOpens in a new window or tabBrand New$87.99Top Rated PlusList price: $160.00 45% offFree shippingFree returns7+ watchers
- Zanzara Smith ZZ1745B Mens Black Leather Lace Up Chukkas Boots 11Opens in a new window or tabBrand New$68.99Top Rated PlusList price: $275.00 75% offFree shippingFree returnsLast one
- Brand New Men's Waterproof Work Boots 6" Nubuck Leather Insulated Hiking AnkleOpens in a new window or tabBrand New$46.70 to $50.30Was: $55.89 10% offFree shippingFree returnsSave up to 5% when you buy more
- Lugz Convoy Fleece MCNVYFGV-7745 Mens Brown Synthetic Casual Dress BootsOpens in a new window or tabBrand New$46.99Top Rated PlusList price: $85.00 45% offFree shippingFree returns
- Lugz Gravel HI MGRAVHD-001 Mens Black Nubuck Lace Up Casual Dress BootsOpens in a new window or tabBrand New$31.99Top Rated PlusList price: $90.00 64% offFree shippingFree returns4+ watchers
- New Men Fashion Army Tactical Comfort Ankle Boots Casual Canvas Lace-up ShoesOpens in a new window or tabBrand New$33.25Was: $35.00 5% off+$12.00 shippingfrom China1+ watchers
- Lugz Rapid MRAPID-060 Mens Black Synthetic Lace Up Casual Dress BootsOpens in a new window or tabBrand New$28.99Top Rated PlusList price: $65.00 55% offFree shippingFree returns13+ watchers
- Lugz Adirondack MADIROD-4037 Mens Gray Nubuck Lace Up Chukkas Boots 7Opens in a new window or tabBrand New$18.99Top Rated PlusList price: $80.00 76% offFree shippingFree returns3 watchers
- Andrew Marc Mens Walden Suede Ankle Chukka Boots Dark Grey/ Black Sizes 9 or 12Opens in a new window or tabBrand New$32.99Was: $49.99 34% off+$7.28 shipping2+ watchers
- Men's Water-resistant Casual Cotton Winter Ankle Snow Boot. Sz 10. Black ($72)Opens in a new window or tabPre-Owned$27.00+$4.95 shipping
- New Mens Lace Up Desert Chukka Boots Oxford Dress Ankle Shoes Vintage Casual USOpens in a new window or tabNew (Other)$37.22Was: $39.60 6% offFree shippingfrom China1+ watchers
- Clarks Wallabee VCY 26166291 Mens Red Suede Lace Up Chukkas BootsOpens in a new window or tabBrand New$54.99Top Rated PlusList price: $150.00 63% offFree shippingFree returns10+ watchers
- Wolverine 1000 Mile Axel W990104 Mens Black Leather Casual Dress BootsOpens in a new window or tabBrand New$195.99Top Rated PlusList price: $400.00 51% offFree shippingFree returns7+ watchers
- Clarks Desert Coal 26166172 Mens Green Suede Lace Up Chukkas BootsOpens in a new window or tabBrand New$89.99Top Rated PlusList price: $170.00 47% offFree shippingFree returns
- Clarks Trek Hi 50 26169535 Mens Gray Suede Lace Up Chukkas BootsOpens in a new window or tabBrand New$105.99Top Rated PlusList price: $160.00 34% offFree shippingFree returns
- Men's Business Casual Lace Up Shoes Faux Leather High Top Ankle Boots Work OLOpens in a new window or tabNew (Other)$64.55Was: $71.72 10% off+$9.99 shippingfrom China
- Lugz Hardwood MHARDWGV-7745 Mens Brown Synthetic Lace Up Casual Dress Boots 13Opens in a new window or tabBrand New$21.99Top Rated PlusList price: $95.00 77% offFree shippingFree returns
- Timberland Suede Ankle Boots Men's Beige Size 9.5 Smart Comfort SystemOpens in a new window or tabPre-Owned$39.98+$12.98 shipping
- Lugz Rapid MRAPID-0466 Mens Gray Synthetic Lace Up Casual Dress BootsOpens in a new window or tabBrand New$32.99Top Rated PlusList price: $65.00 49% offFree shippingFree returns
- Clarks Desert Boot 26156289 Mens Gray Leather Lace Up Chukkas BootsOpens in a new window or tabBrand New$120.99Top Rated PlusList price: $250.00 52% offFree shippingFree returns
- Men Slip On Garden Mules Clogs Sports Sandals Beach Water Slippers Shoes Size USOpens in a new window or tabNew (Other)$12.50Free shippingfrom China
- Dockers Footwear Men's Rawls Ankle BootOpens in a new window or tabBrand New$67.99 to $97.99Free shippingFree returns
- Men's Waterproof Hiking Boots Mid Top Ankle Lightweight Outdoor Trail Work ShoesOpens in a new window or tabBrand New$54.99 to $59.99Was: $68.74 20% offFree shippingExtra 15% off with coupon
- GoldToe Men's White Cotton Ankle Athletic Sock, 6 Pair Shoe Size 12-16Opens in a new window or tabNew (Other)$13.97Free shippingSave up to 15% when you buy more
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