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

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

$125.00

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

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

$125.00

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

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

$125.00

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

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

$125.00

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

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

$125.00

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

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

$125.00

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Sauvie Ii Waterproof Chelsea Boot

Sauvie Ii Waterproof Chelsea Boot

Men's Bogs Sauvie Ii Waterproof Chelsea Boot - Black - Casual boots Comfortable strides await you in this waterproof Chelsea boot enhanced by BOGS Max-Wick to keep you cool and DuraFresh technology to fend off odors. Buoyant cushioning thanks to a... more

$100.00

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Black Boccaccio Ii Chelsea Boots

Black Boccaccio Ii Chelsea Boots

Men's Rombaut Black Boccaccio Ii Chelsea Boots - Casual boots Handcrafted ankle-high buffed faux-leather Chelesa boots in black. more

$460.00 $175.00

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Taupe Nikita Ii Chelsea Boots

Taupe Nikita Ii Chelsea Boots

Men's Eytys Taupe Nikita Ii Chelsea Boots - Brown - Casual boots Ankle-high buffed leather Chelsea boots in taupe. more

$480.00 $250.00

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J. Crew Shoes | J. Crew 2” Chelsea Boot In Saddle Brown | Color: Brown/Tan | Size: 9.5

J. Crew Shoes | J. Crew 2” Chelsea Boot In Saddle Brown | Color: Brown/Tan | Size: 9.5

Never Worn 2” Heeled Boot In Rich Saddle Brown Color. Very Walkable Shoe. Excellent Quality. I Bought Three Pairs Of This Boot, And Am Barely On My Second Pair After Several Years With My First Set. more

$100.00

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Madewell Shoes | Madewell Grayson Brogue Chelsea Boots, Size 8 1/2 | Color: Brown/Tan | Size: 8.5

Madewell Shoes | Madewell Grayson Brogue Chelsea Boots, Size 8 1/2 | Color: Brown/Tan | Size: 8.5

Great Used Condition Only Worn Once Since They Don't Fit Me Top Rated On Madewell! more

$65.00

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Levi's Shoes | Nw Man's Boots Levi's Shoes Chelsea Logger 2.0 Wax Size 13 | Color: Brown | Size: 13

Levi's Shoes | Nw Man's Boots Levi's Shoes Chelsea Logger 2.0 Wax Size 13 | Color: Brown | Size: 13

Walk In Style And Comfort Wearing Levi's Shoes Chelsea Logger 2.0 Wax. Synthetic Upper. Man-Made Lining. Man-Made Removable Insole. Pull-On Style Closure. Raised Platform Round Toe. Ankle Pull Tab. Ankle-Length Shoes. Lug Sole For Comfort. Man-Made... more

$70.00

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KEEN Targhee II Chelsea Boot - Mens 13 Grey Boot Medium

KEEN Targhee II Chelsea Boot - Mens 13 Grey Boot Medium

*Chelsea boot from KEEN *Premium leather upper *Elastic gore panels for easy on and off *Original KEEN fit *Breathable mesh lining *Removable PU insole *EVA midsole *Durable outsole more

$144.95

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KEEN Targhee II Chelsea Boot - Mens 10 Grey Boot Medium

KEEN Targhee II Chelsea Boot - Mens 10 Grey Boot Medium

*Chelsea boot from KEEN *Premium leather upper *Elastic gore panels for easy on and off *Original KEEN fit *Breathable mesh lining *Removable PU insole *EVA midsole *Durable outsole more

$144.95

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KEEN Targhee II Chelsea Boot - Mens 9 Grey Boot Medium

KEEN Targhee II Chelsea Boot - Mens 9 Grey Boot Medium

*Chelsea boot from KEEN *Premium leather upper *Elastic gore panels for easy on and off *Original KEEN fit *Breathable mesh lining *Removable PU insole *EVA midsole *Durable outsole more

$144.95

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Cosmo 2.0 Lug Chelsea Boot - Black - Vagabond Boots

Cosmo 2.0 Lug Chelsea Boot - Black - Vagabond Boots

Women's Vagabond Cosmo 2.0 Lug Chelsea Boot - Black - Ankle boots Sleek leather and a chunky lug sole define the look of this bold boot that is enhanced with stretchy side panels for quick on and off. 1 3/4" heel Leather upper and lining/synthetic sole... more

$200.00

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Sauvie Chelsea Ii Boot - Green - Bogs Boots

Sauvie Chelsea Ii Boot - Green - Bogs Boots

Men's Bogs Sauvie Chelsea Ii Boot - Green - Casual boots Inclement weather can't take a toll on your outdoor adventures when you've got the Bogs Sauvie Chelsea II boot. The redesigned, waterproof boot offers sustainable wear with its REBOUND BLOOM foam... more

$100.00

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Evie Ii Chelsea Boot - Green - Sorel Boots

Evie Ii Chelsea Boot - Green - Sorel Boots

Women's Sorel Evie Ii Chelsea Boot - Green - Ankle boots Bring some rugged charm to a layered look with the Evie II Chelsea boot from SOREL. Treaded detailing on the sole lends secure grip to this suede pair sporting a hidden wedge to take you higher.... more

$80.00

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

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

$125.00

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

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

$125.00

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 10 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 10 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

$119.99 $69.99

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (Size 10 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (Size 10 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

$90.99 $69.99

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

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (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

$119.99 $69.99

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 10 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 10 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

$90.99 $69.99

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (Size 11 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (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

$90.99 $69.99

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

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

$125.00

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

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

$125.00

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Black (Size 11 1/2 W)

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

$90.99 $69.99

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

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

$125.00

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Kicker Ii Waterproof Chelsea Rain Boot

Kicker Ii Waterproof Chelsea Rain Boot

Men's Bogs Kicker Ii Waterproof Chelsea Rain Boot - Blue - Casual boots A sturdy rubber upper adds adventure-ready durability to a sporty Chelsea boot featuring a low-profile silhouette and moisture-wicking tech for total comfort. Waterproof: protects... more

$85.00

FREE shipping

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Purple Boccaccio Ii Apple Leather Chelsea Boots

Purple Boccaccio Ii Apple Leather Chelsea Boots

Men's Rombaut Purple Boccaccio Ii Apple Leather Chelsea Boots - Casual boots Ankle-high buffed faux-leather boots in purple. more

$420.00 $126.00

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

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

$125.00

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Classic Casual Ii Chelsea Boot

Classic Casual Ii Chelsea Boot

Men's Bogs Classic Casual Ii Chelsea Boot - Black - Casual boots Stay protected in the Bogs Classic Casual II Chelsea boot. Crafted with rubber, the waterproof boot features an eco-friendly BLOOM footbed that promotes a sustainable initiative.... more

$149.99

FREE shipping

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Kicker Ii Waterproof Chelsea Rain Boot

Kicker Ii Waterproof Chelsea Rain Boot

Men's Bogs Kicker Ii Waterproof Chelsea Rain Boot - Brown - Casual boots A sturdy rubber upper adds adventure-ready durability to a sporty Chelsea boot featuring a low-profile silhouette and moisture-wicking tech for total comfort. Waterproof: protects... more

$85.00

FREE shipping

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

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

$125.00

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Johnny 2.0 Chelsea Boot

Johnny 2.0 Chelsea Boot

Men's Vagabond Johnny 2.0 Chelsea Boot - Black - Casual boots Dual goring panels and a rear pull-tab offer easy wear on a rich leather Chelsea boot grounded by a durable lug sole. Leather upper and lining/rubber sole Imported more

$220.00

FREE shipping

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Sauvie Ii Chelsea Rain Boot

Sauvie Ii Chelsea Rain Boot

Women's Bogs Sauvie Ii Chelsea Rain Boot - Black - Wellington boots Enjoy rainy days in the Bogs Sauvie II Chelsea rain boot. This waterproof pair sports Rebound cushioning, BLOOM EVA foam, 3mm Neo-Tech waterproof insulation, BioGrip slip-resistant... more

$94.99

FREE shipping

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (Size 11 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Red Wood (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

$90.99 $69.99

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Black Boccaccio Ii Chelsea Boots

Black Boccaccio Ii Chelsea Boots

Men's Rombaut Black Boccaccio Ii Chelsea Boots - Casual boots Handcrafted ankle-high patent faux-leather Chelsea boots in black. more

$460.00 $281.00

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Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (Size 11 1/2 W)

Wide Width Men's Deer Stags® Rockland Chelsea Boots by Deer Stags in Brown (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

$119.99 $69.99

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More information about Men's Shoes

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