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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 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

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

Chelsea Boots, Ankle Boots

Men's Santoni Chelsea Boots, Ankle Boots - Blue - Casual boots Chelsea' suede ankle boots with elastic side inserts, contrast lining, back logo tab and rubber sole. Colours: Blue Composition: 100% leather Dimension: UK MEN MPN: MGSI13414SMAISYWU60.... 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

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

J. Crew Shoes | J. Crew Gray Leather Ankle Chelsea Boot W/ Ankle Strap And Gold Hardware- Size 8 | Color: Gray | Size: 8

J. Crew Gray Leather Chelsea Ankle Boot. Made In Italy With 2 Inch Heel, Ankle Strap And Gold Hardware. 03868 Color: Gray Size: Women's 8 more

Blair Men's Deer Stags Rockland Chelsea Boots - Black - 12 - Medium

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

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

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

Free People Shoes | Free People Essential Chelsea Boots In Natural Cream Ankle Boots Size 38 Euc | Color: Cream | Size: 8

Free People Tan Leather Ankle Boots Made In Spain Size 38/8 Euc No Box more

DUNLOP 8610433 Size 13 Men's Steel Rubber Boot, Black

Rubber Boot, Shoe Style Ankle, Toe Type Steel, Footwear Sole Pattern Cleated, Insulated No, Size 13, Footwear Width D, Men's, Boot Height 6 in, Metatarsal Guard No, Waterproof Yes, 1 Pair more

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

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

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

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 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 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

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

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

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

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

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

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 Dark Brown (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 Tan (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

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

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 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

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

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 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