Men's Shoes › two toned chelsea ankle boots

Men's TREVINO Ankle Boots by Drew in Black 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

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

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

Chelsea Ankle Boots

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

Slip-on Chelsea Ankle Boots

Men's Tod's Slip-on Chelsea Ankle Boots - Brown - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 1.5cm 100% Calf Leather, 100% Rubber. Made in Italy. more

Madewell Shoes | Madewell The Cait Two Toned Brown Suede Side Zip Ankle Boots Size 7 | Color: Brown/Tan | Size: 7

Suede And Leather Two Toned Color Zips Up The Side Ankle Height Great Condition Some Wear On The Suede more

Madewell Shoes | Madewell Regan Ankle Boots - Leather Chunky Heel Black Ankle/Chelsea Boot | Color: Black | Size: 7.5

Reposhing This Item I Purchased From @Cooldudz. Used 1x For A Wedding Rehearsal And Now That I Am Working From Home I Don’t Wear/Need Heels Anymore. Loved Them, Fit Well And Very Stylish. more

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Black/Black 12 M2A-000-BLK-120

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Black/Black 12 M2A-000-BLK-120. Muck Boots crafted these Men's Footwear with 4mm of Neoprene insulation for maximum warmth when working outdoors on those chilly days. A high traction rubber... more

Keen Targhee II Mid WP Hiking Boots Leather/Synthetic Men's, Shitake/Brindle SKU - 941365

The Keen Targhee II Mid WP Hiking Boots keep your feet dry and lets them breathe. The aggressive outsole bites into the terrain. It's built for all-day comfort and the mid-cut height adds ankle support.Features4mm multi-directional lugsContoured heel... more

Madewell Shoes | Madewell Walker Chelsea Olive Green Suede 2” Heeled Ankle Boot - Size 9 | Color: Green | Size: 9

Madewell Walker Chelsea Suede Ankle Boot - Size 9 Retail Price $$188.00 + Tax In Supersoft Suede, These Sleek Chelsea Boots Give A Low-Key Nod To Timeless '60s Styles. The Not-Too-High Heel Is Made For Adventuring Day Or Night. 2" Heel. Suede Upper.... more

WIDE FIT Darcy Chelsea Boot - black

Elevate your look with the Darcy Chelsea Boot. Perfect for AM to PM, enjoy the stylish detailing and ultra comfortable cushioned insoles. Key Features Include:- Rounded toe ankle boot- Wide width fit- Side zip closure- Cloudwalkers cushioned insole-... more

Lowa Alpine Expert II GTX Insulated Hunting Boots Leather Men's, Dark Brown/Black SKU - 776283

The Lowa Alpine Expert II GTX Leather Men's Insulated Hunting Boots are versatile alpine boots for mixed climbing, heavy backpack and hunting trips. This boot features FLEXFIT-SYNCHRO for comfortable ankle flex and a generous rocker shape for easy... more

Lowa Alpine Expert II GTX Insulated Hunting Boots Leather Men's, Dark Brown/Black SKU - 303405

The Lowa Alpine Expert II GTX Leather Men's Insulated Hunting Boots are versatile alpine boots for mixed climbing, heavy backpack and hunting trips. This boot features FLEXFIT-SYNCHRO for comfortable ankle flex and a generous rocker shape for easy... more

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (Size 9 1/2 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

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 9 1/2 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

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Black/Black 11 M2A-000-BLK-110

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Black/Black 11 M2A-000-BLK-110. 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

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Moss/Green 11 M2A-300-GRN-110

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Moss/Green 11 M2A-300-GRN-110. 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

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Moss/Green 11 M2A-300-GRN-110

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Moss/Green 11 M2A-300-GRN-110. Muck Boots crafted these Men's Footwear with 4mm of Neoprene insulation for maximum warmth when working outdoors on those chilly days. A high traction rubber... more

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 Footwear with 4mm of Neoprene insulation for maximum warmth when working outdoors on those chilly days. A high traction rubber... more

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Black/Black 12 M2A-000-BLK-120

Muck Boots Muckster 2 Ankle Muck Outdoor Casual Boot - Men's Black/Black 12 M2A-000-BLK-120. 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

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

Men's TREVINO Ankle Boots by Drew in Black 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

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

Men's TREVINO Ankle Boots by Drew in Black 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

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 14 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

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

Men's TREVINO Ankle Boots by Drew in Black 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

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 10 6E)

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

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

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

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

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

Men's TREVINO Ankle Boots by Drew in Black Leather (Size 9 6E)

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

Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 9 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

Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (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

Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (Size 11 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

Extra Wide Width Men's Propét® Blizzard Ankle-Zip Boot by Propet in Black (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

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (Size 9 1/2 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