Men's Casual Ankle Boots and Booties
38 items found
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![Brown Polo Ralph Lauren Asher Suede Chukka Boot](https://m.media-amazon.com/images/I/71oRs2Ec+YL._AC_SR768,1024_.jpg)
![Brown Polo Ralph Lauren Asher Suede Chukka Boot](https://m.media-amazon.com/images/I/61DHqKxrtlL._AC_SR768,1024_.jpg)
![Black Red Wing Heritage Lace-up boot](https://m.media-amazon.com/images/I/61nbEJxAK2L._AC_SR768,1024_.jpg)
![Black Red Wing Heritage Lace-up boot](https://m.media-amazon.com/images/I/51EsUUsEivL._AC_SR768,1024_.jpg)
![Tan Florsheim Renegade 4-Eye Boot](https://m.media-amazon.com/images/I/71M-Pxqra0L._AC_SR768,1024_.jpg)
![Tan Florsheim Renegade 4-Eye Boot](https://m.media-amazon.com/images/I/61ZtC1AOLuL._AC_SR768,1024_.jpg)
![Brown TOMS Griffin](https://m.media-amazon.com/images/I/61OEEQAU0eL._AC_SR768,1024_.jpg)
![Brown TOMS Griffin](https://m.media-amazon.com/images/I/51cf5nnBpdL._AC_SR768,1024_.jpg)
![Gray Dr. Martens Anistone Lo Leather Boots](https://m.media-amazon.com/images/I/71PWwlhNffL._AC_SR768,1024_.jpg)
![Gray Dr. Martens Anistone Lo Leather Boots](https://m.media-amazon.com/images/I/61jSlEmt1wL._AC_SR768,1024_.jpg)
![Black Cole Haan Originalgrand Remastered Waterproof Chukka Boots](https://m.media-amazon.com/images/I/61XIgLYPezL._AC_SR768,1024_.jpg)
![Black Cole Haan Originalgrand Remastered Waterproof Chukka Boots](https://m.media-amazon.com/images/I/61lU-rSqWsL._AC_SR768,1024_.jpg)
![Tan Florsheim Rucci Wingtip Lace Boot](https://m.media-amazon.com/images/I/71ElUykurQL._AC_SR768,1024_.jpg)
![Tan Florsheim Rucci Wingtip Lace Boot](https://m.media-amazon.com/images/I/71YrlTcmfsL._AC_SR768,1024_.jpg)
![Brown Rockport Flynn](https://m.media-amazon.com/images/I/718vBdNM1aL._AC_SR768,1024_.jpg)
![Brown Rockport Flynn](https://m.media-amazon.com/images/I/71HHCbqP+8L._AC_SR768,1024_.jpg)
![Black Hey Dude Branson Classic](https://m.media-amazon.com/images/I/71HAluZPTML._AC_SR768,1024_.jpg)
![Black Hey Dude Branson Classic](https://m.media-amazon.com/images/I/81i42IiVUNL._AC_SR768,1024_.jpg)
![Tan Dansko Daisie](https://m.media-amazon.com/images/I/71nAmp07J7L._AC_SR768,1024_.jpg)
![Tan Dansko Daisie](https://m.media-amazon.com/images/I/516LP7FI2wL._AC_SR768,1024_.jpg)
![Gray Timberland Redwood Falls Waterproof Chukkas](https://m.media-amazon.com/images/I/61mY6h765RL._AC_SR768,1024_.jpg)
![Gray Timberland Redwood Falls Waterproof Chukkas](https://m.media-amazon.com/images/I/71wA6IrhrQL._AC_SR768,1024_.jpg)
![Black Dansko Perrin](https://m.media-amazon.com/images/I/71tJg28Q77L._AC_SR768,1024_.jpg)
![Black Dansko Perrin](https://m.media-amazon.com/images/I/71NOBBukD4L._AC_SR768,1024_.jpg)
![Brown UGG Venture Daze Ultra Mini](https://m.media-amazon.com/images/I/71puDGgf6LL._AC_SR768,1024_.jpg)
![Brown UGG Venture Daze Ultra Mini](https://m.media-amazon.com/images/I/71LuYsXSvDL._AC_SR768,1024_.jpg)
![Brown UGG Venture Daze Ultra Mini](https://m.media-amazon.com/images/I/61iSKD3a1UL._AC_SR768,1024_.jpg)
![Brown UGG Venture Daze Ultra Mini](https://m.media-amazon.com/images/I/71dxi2Y3IJL._AC_SR768,1024_.jpg)
![Brown Timberland Newmarket Mid Lace Up](https://m.media-amazon.com/images/I/61BPhL3UWUL._AC_SR768,1024_.jpg)
![Brown Timberland Newmarket Mid Lace Up](https://m.media-amazon.com/images/I/613xTqdTK-L._AC_SR768,1024_.jpg)
![Brown Timberland Redwood Falls Waterproof](https://m.media-amazon.com/images/I/71W3BwDVBtL._AC_SR768,1024_.jpg)
![Brown Timberland Redwood Falls Waterproof](https://m.media-amazon.com/images/I/71vMTk-s53L._AC_SR768,1024_.jpg)
![Brown Johnston & Murphy Raleigh Double Buckle Boots](https://m.media-amazon.com/images/I/71Bw9jrMdrL._AC_SR768,1024_.jpg)
![Brown Johnston & Murphy Raleigh Double Buckle Boots](https://m.media-amazon.com/images/I/71lhRdvaYhL._AC_SR768,1024_.jpg)
![Tan Nunn Bush Karnak Plain Toe Boot Chukka](https://m.media-amazon.com/images/I/716AQU54sAL._AC_SR768,1024_.jpg)
![Tan Nunn Bush Karnak Plain Toe Boot Chukka](https://m.media-amazon.com/images/I/81waa5QSduL._AC_SR768,1024_.jpg)
![Tan Timberland Britton Road Mid Lace Up Waterproof](https://m.media-amazon.com/images/I/71121JDqaoL._AC_SR768,1024_.jpg)
![Tan Timberland Britton Road Mid Lace Up Waterproof](https://m.media-amazon.com/images/I/71RcOcI2UHL._AC_SR768,1024_.jpg)
4 left in stock
![Tan AllSaints Booker Suede Boot](https://m.media-amazon.com/images/I/71smO1-mGIL._AC_SR768,1024_.jpg)
![Tan AllSaints Booker Suede Boot](https://m.media-amazon.com/images/I/61abUp35MIL._AC_SR768,1024_.jpg)
2 left in stock
![Black AllSaints Booker Boot](https://m.media-amazon.com/images/I/51uIy6lwx7L._AC_SR768,1024_.jpg)
![Black AllSaints Booker Boot](https://m.media-amazon.com/images/I/51XwNIF2fEL._AC_SR768,1024_.jpg)
1 left in stock
![Tan AllSaints Jacques Suede Boot](https://m.media-amazon.com/images/I/71liUkDH3CL._AC_SR768,1024_.jpg)
![Tan AllSaints Jacques Suede Boot](https://m.media-amazon.com/images/I/81xoaOCRQYL._AC_SR768,1024_.jpg)
![Brown Eastland 1955 Edition Belgrade](https://m.media-amazon.com/images/I/71BuPZTeUcL._AC_SR768,1024_.jpg)
![Brown Eastland 1955 Edition Belgrade](https://m.media-amazon.com/images/I/71Pav-TJs8L._AC_SR768,1024_.jpg)
6 left in stock
![Black Marc Joseph New York Grand Ave](https://m.media-amazon.com/images/I/71X4SN1twTL._AC_SR768,1024_.jpg)
![Black Marc Joseph New York Grand Ave](https://m.media-amazon.com/images/I/6155Y4DvUrL._AC_SR768,1024_.jpg)
![Black Stacy Adams Sotaro Heeled Boot](https://m.media-amazon.com/images/I/71k8VY5rRsL._AC_SR768,1024_.jpg)
![Black Stacy Adams Sotaro Heeled Boot](https://m.media-amazon.com/images/I/51bpzeP8BPL._AC_SR768,1024_.jpg)
1 left in stock
![Black UGG Skyview Classic Pull-On](https://m.media-amazon.com/images/I/617K0D6SPJL._AC_SR768,1024_.jpg)
![Black UGG Skyview Classic Pull-On](https://m.media-amazon.com/images/I/71Dz8SThK7L._AC_SR768,1024_.jpg)
1 left in stock
![Brown Dingo Road Trip](https://m.media-amazon.com/images/I/61asvA9LtxL._AC_SR768,1024_.jpg)
![Brown Dingo Road Trip](https://m.media-amazon.com/images/I/61ZZvP0Q-lL._AC_SR768,1024_.jpg)
![Black Stacy Adams Santos Plain Toe Side Zip Boot](https://m.media-amazon.com/images/I/81pcieEMvKL._AC_SR768,1024_.jpg)
![Black Stacy Adams Santos Plain Toe Side Zip Boot](https://m.media-amazon.com/images/I/81IOgNoerjL._AC_SR768,1024_.jpg)
4 left in stock
2 left in stock
1 left in stock
6 left in stock
1 left in stock
1 left in stock