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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 11 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

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 11 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 12 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 14 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 9 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Wide Width Men's Daily Double Chelsea Boots by Eastland® in Black (Size 12 W)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 10 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Wide Width Men's Daily Double Chelsea Boots by Eastland® in Black (Size 9 1/2 W)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Calf Hair Ankle Boots Boots, Ankle Boots

Men's Lidfort Calf Hair Ankle Boots Boots, Ankle Boots - Black - Casual boots Calf hair ankle boots with leather sole and aelastic detail. Colours: Black Composition: 100% calf leather Dimension: UK MEN 25 mm heels MPN: 625CAVALLINONERO. 100% calf... more

Braided Leather Ankle Boots Boots, Ankle Boots

Men's Lidfort Braided Leather Ankle Boots Boots, Ankle Boots - Black - Casual boots Braided leather ankle boots with elastic ankle straps, leather sole. Colours: Black Composition: 100% calfskin leather (Bos Taurus) Dimension: UK MEN MPN:... more

Muck Boots Chore Chelsea CSA Steel Toe Boots - Men's Black 9 CCST-CSA-BLK-090

Muck Boots Chore Chelsea CSA Steel Toe Boots - Men's Black 9 CCST-CSA-BLK-090. These Muck Boot Chore CSA Steel Toe Men's Rubber Boots are built to provide the 100percent waterproof protection you need to handle any mess from mud to grime. These Men's... more

Muck Boots Chore Chelsea CSA Steel Toe Boots - Men's Black 11 CCST-CSA-BLK-110

Muck Boots Chore Chelsea CSA Steel Toe Boots - Men's Black 11 CCST-CSA-BLK-110. These Muck Boot Chore CSA Steel Toe Men's Rubber Boots are built to provide the 100percent waterproof protection you need to handle any mess from mud to grime. These Men's... more

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

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 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 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

Dryshod Evalusion Ankle Rubber Boots Rubber Men's, Black/White SKU - 870942

When you dont need a tall boot, but still need comfortable protection, the Dryshod Evalusion Ankle Boot is ideal. Its like stepping into your favorite slippers. Dryshod's new super lightweight DUREVA outsole is built for high-endurance outdoor... more

Dryshod Evalusion Ankle Rubber Boots Rubber Men's, Black/White SKU - 734261

When you dont need a tall boot, but still need comfortable protection, the Dryshod Evalusion Ankle Boot is ideal. Its like stepping into your favorite slippers. Dryshod's new super lightweight DUREVA outsole is built for high-endurance outdoor... 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

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 11 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

Stef Chelsea Ankle Boots

Men's Ann Demeulemeester Stef Chelsea Ankle Boots - Black - Casual boots Synonymous with timeless elegance, the Chelsea boot gets a low-key update from Ann Demeulemeester. A menswear classic, they will go with a navy or grey suit, or with jeans and a... more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 10 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Ankle Boots In Leather With Metallic Stacked-logo Trim

Women's HUGO Ankle Boots In Leather With Metallic Stacked-logo Trim - Black Modern ankle boots by HUGO, crafted in smooth leather with a metallic stacked-logo trim, harness-style strap and tapered 5cm heel. more

Chelsea Ankle Boots

Men's Tod's Chelsea Ankle Boots - Black - Casual boots Dimensions: Heel: 3.5cm, Height: 15.5cm, Sole: 2cm 100% Calf Leather, 100% Rubber. Made in Italy. 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

Henry Ankle Chelsea Boot

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

Kate Spade Shoes | Kate Spade Chelsea Boot Rain Boots Woman’s Sedgwick Ankle Boots | Color: Black | Size: 10/11

Used Read Description Size: 10/11 Measurements: Details: No Rips Or Stains Condition:Good Smoke Free Home Always Open To Offers more

Xtratuf 6 in Ankle Deck Boot - Men's Black/Snorkel Blue 7 XMAB-002-BLK-070

Xtratuf 6 in Ankle Deck Boot - Men's Black/Snorkel Blue 7 XMAB-002-BLK-070. Anglers are athletes and they need proper footwear to help them perform at their best. This lightweight silhouette has the same XTRATUF non-marking slip resistant Chevron... more

WIDE FIT Sarah Ankle Boot - black

Our Sarah Ankle Boot is an elevated addition to your footwear collection. With its faux leather fabrication, faux fur lining, and front lace-up detail this boot is a stylish piece that brings the perfect finishing touch to your look. Key Features... more

WIDE FIT Sarah Ankle Boot - black

Our Sarah Ankle Boot is an elevated addition to your footwear collection. With its faux leather fabrication, faux fur lining, and front lace-up detail this boot is a stylish piece that brings the perfect finishing touch to your look. Key Features... more

Dryshod Legend Ankle Work Boots Densoprene Men's, Black/Camo SKU - 617447

When you dont need a tall boot, but still need protection, the Dryshod Legend Ankle Work Boots are ideal. Its like stepping into your favorite slippers. Upgraded sole provides superior traction and stability for everyday wear.FeaturesAggressive... more

Blair Men's Deer Stags Rockland Chelsea Boots - Black - 10 - 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

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

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

WIDE FIT Western Ankle Boot - black

Bring glamorous fashion vibes with the Western Ankle Boot. Work and play with these pair, flaunting a block stacked heel, fabulous faux suede fabrication and pointed closed toe, you'll definitely be comfortably chic wherever you go.Key Features... more

Muck Boots Chore Classic Chelsea Boots - Men's Black 10 CHC-000A-BLK-100

Muck Boots Chore Classic Chelsea Boots - Men's Black 10 CHC-000A-BLK-100. These from Muck Boots are crafted with a 5mm neoprene bootie to keep your feet comfortable and protected. For extra-strength protection the Muck Chore Classic Chelsea features... more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 11 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 9 1/2 M)

These handsome Chelsea boots from Eastland® are one of the most versatile pairs of shoes you'll own. The memory foam comfort insole supports and conforms to feet while the TPR outsole enhances flexibility, slip resistance, insulation, and durability.... more