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    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 D)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 D)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 1/2 D)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 1/2 D)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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    Best Seller
    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EEEE)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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    Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

    Blair Men's Deer Stags Rockland Chelsea Boots - Black - 9 - Womens

    Deer Stags® Rockland Chelsea Boots deliver style and comfort, hitting above the ankle to avoid irritation and provide added support. This handsome boot can be worn all year long. Deer Stags items are not eligible for additional discounts or special... more

    $69.99

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    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 168992

    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 168992

    The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

    $229.95

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    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 562692

    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 562692

    The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

    $229.95

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    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 557201

    Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 557201

    The Danner Bull Run Chelsea Work Boots provide electrical hazard protection to ASTM F2892-18 EH standards and feature a durable, oiled, full grain leather upper. These boots are both durable and comfortable, with slip on action, making them perfect for... more

    $229.95

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    Muck Boots Outscape Chelsea Boot - Men's Coffee Bean/Crockery/Black/Ribbon Red 9 OSC-900-BRN-090

    Muck Boots Outscape Chelsea Boot - Men's Coffee Bean/Crockery/Black/Ribbon Red 9 OSC-900-BRN-090

    Muck Boots Outscape Chelsea Boot - Men's Coffee Bean/Crockery/Black/Ribbon Red 9 OSC-900-BRN-090. Dedicated to building footwear that is 100percent MUCKPROOF remarkably protective exceptionally comfortable and totally waterproof. The all new Outscape... more

    $135.00

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    Muck Boots Arctic Excursion Ankle Rubber Boot - Men's Brown 7 AELA-900-BRN-070

    Muck Boots Arctic Excursion Ankle Rubber Boot - Men's Brown 7 AELA-900-BRN-070

    Muck Boots Arctic Excursion Ankle Rubber Boot - Men's Brown 7 AELA-900-BRN-070. The fleece lining offers superior comfort softness and durability while the EVA midsole delivers lightweight cushioning and support on long cold treks. Featuring flexible 5... more

    $155.00

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

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    Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Bark/Otter 8 M2A-900-BRN-080

    Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Bark/Otter 8 M2A-900-BRN-080

    Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Bark/Otter 8 M2A-900-BRN-080. Muck Boots crafted these Men's Rain Boots with 4mm of Neoprene insulation for maximum warmth when working outdoors on those chilly days. A high traction rubber... more

    $130.00

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 8 LDB-STL-BRN-080. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

    FREE shipping

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    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090

    Xtratuf 6in Legacy Steel Toe Ankle Deck Boot - Men's Brown 9 LDB-STL-BRN-090. The Legacy Chelsea features the same Commercial Grade performance and safety features of the classic Legacy Boot but with functional pull tabs and a twin elastic gore for... more

    $155.00

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    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Brown/Tan | Size: 7

    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond Color 7 | Color: Brown/Tan | Size: 7

    Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more

    $128.00

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    Chelsea Ankle Boots

    Chelsea Ankle Boots

    Men's Tod's Chelsea Ankle Boots - Brown - Casual boots 100% Suede, 100% Rubber. Made in Italy. more

    $587.78 $479.63

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    Henry Country Ankle Chelsea Boot

    Henry Country Ankle Chelsea Boot

    Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. more

    $732.05 $597.36

    FREE shipping

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    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Tan | Size: Various

    Free People Shoes | Free People James Chelsea Boots Ankle Boots Tan Brown Almond 7 | Color: Brown/Tan | Size: Various

    Details Make A Statement In These So Cool Leather Chelsea Boots Featured In A Chunky Heeled Design With Elastic Side Details And A Slim Silhouette. These Boots Feature Intentionally Distressed Detailing For A Worn-In Look. Side Zipper Closure Cushioned... more

    $128.00

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    WIDE FIT Valentina Ankle Boot - brown

    WIDE FIT Valentina Ankle Boot - brown

    Step out in style with our Valentina Ankle Boot. Complete in a cushioned wide width fit for ultimate comfort, you'll love the faux leather finish and buckle detailing. Key Features Include:- Round toe ankle boot- Wide width fit- Side zip closure-... more

    $99.99 $69.99

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    Chelsea Ankle Boots

    Chelsea Ankle Boots

    Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 4cm, Height: 14cm, Sole: 2.5cm 100% Leather, 100% Rubber, 72% Polyester, 28% Elastane. Made in Italy. more

    $662.59 $572.48

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    Madewell Shoes | Madewell Ivy Croc Leather Chelsea Boots Lug Sole Platform Ankle Boots Like New | Color: Brown | Size: 8

    Madewell Shoes | Madewell Ivy Croc Leather Chelsea Boots Lug Sole Platform Ankle Boots Like New | Color: Brown | Size: 8

    Madewell Size 8 The Ivy Croc Embossed Leather Chelsea Boots Ankle Boots In Brown Platform Utilitarian Lug Soles In Excellent Almost Like New Condition. Very Clean Inside & Out. Tags: Classic Chunky Lug Soles Neutral Versatile Business Casual Office... more

    $75.00

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    GEORGIA BOOT GR530 Size 10.5 Men's Chelsea Boot Steel Work Boot, Soggy Brown

    GEORGIA BOOT GR530 Size 10.5 Men's Chelsea Boot Steel Work Boot, Soggy Brown

    Chelsea Boot, Style Family Chelsea Boot, Metatarsal Guard No, ASTM Standards Met Compression (C/75), Impact (I/75), Closure Slip On, Chemical Resisting Sole Yes, Color Soggy Brown, Width M, Gender Men's, Heel Definition Defined Heel, Non Metallic Upper... more

    $132.00

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    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 11 1/2 D)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 11 1/2 D)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

    go to store
    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EE)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 EE)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

    go to store
    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 EE)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 1/2 EE)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

    go to store
    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EE)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

    go to store
    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EEEE)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 9 EEEE)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 D)

    Men's TREVINO Ankle Boots by Drew in Brown Leather (Size 10 D)

    Drew Trevino are casual, yet comfortable ankle boots that combine sleek styling with a host of foot health benefits. These Drew therapeutic shoes offer two removable insoles. Keep both in for added depth or remove one for double-added depth. Drew... more

    $220.99

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    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 W)

    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 W)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 9 M)

    Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 9 M)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 16 W)

    Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 16 W)

    These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more

    $119.99 $69.99

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    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 10 W)

    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 10 W)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 8 M)

    Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 8 M)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 14 W)

    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 14 W)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 8 1/2 M)

    Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 8 1/2 M)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 14 M)

    Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 14 M)

    These Deer Stags® Rockland Chelsea Boots are a must-have style for formal and casual situations. A memory foam sock and a grippy durable TPR outsole add cushion and support. Faux leatherMemory foam sock linerMoisture-wicking liningTPR outsolesPull-tabs... more

    $119.99 $69.99

    go to store
    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 10 1/2 W)

    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 10 1/2 W)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 1/2 W)

    Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 1/2 W)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 10 1/2 EW)

    Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 10 1/2 EW)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 8 EW)

    Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 8 EW)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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    Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 1/2 EW)

    Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Brown (Size 11 1/2 EW)

    A rugged, waterproof cold weather boot designed to keep out the elements—rain, sleet or snow. The rugged leather upper of this Propet® Blizzard Ankle-Zip Boot features a molded rubber toe. Easy on and off zip closure means you can leave them by the... more

    $89.95

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