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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

Larue Chelsea Ankle Boots

Men's Moncler Larue Chelsea Ankle Boots - Blue - Casual boots Larue Chelsea ankle boots in leather. Round toe Elasticated side panels Rear pull tab Rear logo ring Embossed logo at midsole Debossed logo at heel cap. 100% Leather. more

Men's Daily Double Chelsea Boots by Eastland® in Black (Size 9 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

Beatles Leather Ankle Boots

Men's Tod's Beatles Leather Ankle Boots - Gray - Casual boots Tods mens boots. Shoe style: ankle boots. Upper material: leather. Solematerial: rubber. Tods mens black beatles leather ankle boots. Ankle boots in leather with side elastic inserts,... more

Henry Country Ankle Chelsea Boot

Men's Tricker's Henry Country Ankle Chelsea Boot - Brown - Casual boots 100% Leather. Made in Italy. 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 Tan (Size 11 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 14 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 Dark Brown (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

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

Danner Bull Run Chelsea Work Boots Full Grain Leather Men's, Brown SKU - 333815

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

Men's Daily Double Chelsea Boots by Eastland® in Tan (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

Men's Daily Double Chelsea Boots by Eastland® in Dark Brown (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

Henry Ankle Chelsea Boot

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

Men's Murphy Casual Boots by Drew in Black Nubuck Leather (Size 14 6E)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines 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. The... 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

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

Grundens Deck Boss Ankle Boots Rubber Men's, Monument Grey SKU - 516600

The Grundens Deck-Boss Ankle Boots were designed to provide anglers with comfortable performance driven footwear options that will outlast even the longest days on the water. Grundens has prioritized a thicker insole to promote noticeable shock... 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 Evalusion Ankle Rubber Boots Rubber Men's, Camo/Bark SKU - 592563

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

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 Width Men's Murphy Casual Boots by Drew in Camel Leather (Size 11 1/2 W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines 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. The... more

Men's Murphy Casual Boots by Drew in Camel Leather (Size 12 4W)

Drew Murphy is a mens casual, yet comfortable ankle boot that combines 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. The... more

Men's Daily Double Chelsea Boots by Eastland® in Dark Brown (Size 13 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 Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 14 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 FIT Eliana Ankle Boot - black

Simplicity, comfort, and endless style come together in the faux suede fabrication of our Eliana Ankle Boot. The wide fit, mid block heel, and ankle boot style ensure your comfort throughout the day. Key Features Include:- Round toe- Ankle boot design-... more

WIDE FIT Rita Ankle Boot - black

The Rita Ankle Boot is the perfect combination of style and comfort to keep you strutting all season long. You'll feel right at ease in the wide fit of this ankle boot with a supportive block heel.Key Features Include:- Round toe ankle boot- Wide width... more

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot w/Steel Toe - Men's Wide Brown 10 GB00337-100W

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot w/Steel Toe - Men's Wide Brown 10 GB00337-100W. Built with a combination cement and San Crispino construction the upper is crafted from full-grain SPR leather and features twin gore panels and... more

Georgia Boot Athens Chelsea Waterproof 5 inch Work Boot - Men's Dark Brown 10 Wide GB00156-100W

Georgia Boot Athens Chelsea Waterproof 5 inch Work Boot - Men's Dark Brown 10 Wide GB00156-100W. This men's Chelsea boot's upper is made from a supple full-grain leather and also includes elastic twin gores. The twin gores make the boot easy to slip on... more

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 8.5 GB00315-085W

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot - Men's Wide Brown 8.5 GB00315-085W. The upper is constructed from full-grain SPR leather with twin gore panels and nylon pull tabs. The Georgia Waterproof System will keep your feet protected... more

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot w/Steel Toe - Men's Medium Brown 11 GB00337-110M

Georgia Boot Eagle One Waterproof Chelsea 4 inch Work Boot w/Steel Toe - Men's Medium Brown 11 GB00337-110M. Built with a combination cement and San Crispino construction the upper is crafted from full-grain SPR leather and features twin gore panels... 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 Tan (Size 9 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 Dark Brown (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

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