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Ted Baker Men’s Hourb Chelsea Boot, Black Leather, 8.5 M US

Chelsea boot

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Hush Puppies Men’s Thor Hamlin Chelsea Boot, Charcoal, 8.5 M US

Thor Hamlin

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FRYE Men’s James Chelsea Boot, Cognac Smooth Vintage Leather, 8.5 M US

You’ll never regret teaming up with the handsome Frye James Chelsea boot, a perennial classic that’s sure to improve your street cred. Equipped with generous stretch side panels, this men’s pull-on ankle boot is masterfully crafted from premium, hand-burnished leather finished with a special white wax that improves with age. The leather sole, too, is built to last and last.

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Sebago Men’s Rutland Chelsea Boot, Medium Brown, 8.5 M US

Find effortless style and comfort in the Sebago Rutland Chelsea. Boasting a minimalistic leather upper with burnished detail, this boot offers a put-together look. The dual-side, stretch fabric panels adjust to the perfect fit to enhance comfort while walking.

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Clarks Originals Men’s Desert Boot,Beeswax,8.5 M US

Inspired by the crepe-soled boots worn by British officers in World War II, this handsome chukka delivers comfort and a classic look.

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Laredo Men’s Paris Western Boot,Black,8.5 D US

Take the look of your favorite cowboy boots to work, in a pair that’ll stand up to the job. The Laredocowboy work boot has a leather foot under a 12″ fancy stitched manmade shaft. Manmade lining. Medium toe and cowboy heel. EW, Extra Wide, equals EE width.

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Clarks Men’s Bushacre 2 Boot,Dark Brown,8.5 M US

Honor your adventurous spirit in the Clarks Bushacre 2 boot, a take on the iconic Clarks Desert Boot. This men’s chukka boot features a suede or leather upper and a two-eye lace closure with reinforced metal eyelets. A soft synthetic lining and cushioned footbed provide interior comfort. The Clarks Bushacre 2 ankle boot is finished with a synthetic crepe sole for shock absorption and a classic foundation.

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Calvin Klein Men’s Brogan Boot, Black, 8.5 M US

Detailed stitching. Synthetic lining. Lightly padded footbed. Man-made outsole. Stacked heel. Imported.

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Giorgio Brutini Men’s 660591 Boot,Black,8.5 D US

Plain toe pull-on boot. Elastic side gore for easy-on comfort. Micro fiber padded sock. Polyurethane lightweight comfort sole.

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Ariat Men’s Sport Square Toe Western Boot, Earth/Black, 8.5 2E US

The Ariat Sport boots feature a smooth leather foot under a fancy stitched 13″ leather shaft. 2″ cowboy heel. With Ariat, you can have no worries about all day comfort Imported. Ariat Four Layer Rebound (4LR) Technology offers Ariat quality comfort at an exceptional value. The Ariat 4LR footbed, featuring EVA cushioning, is combined with a moisture wicking sock liner and a metatarsal support pad to maintain all-day comfort and support. Integrated, non-removable insole.

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Ben Sherman Men’s Vince Boot, Cognac, 8.5 M US

Lace up, chukka style boot. Contrasting metal eyelets. Contrast stitching detail. Leather logo patch hit on tongue. Fabric lining, cushioned insole. Synthetic outsole. Imported.

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Eastland Men’s Seneca Chukka Boot, Natural, 8.5 D US

An Eastland camp moc classic in five-eye chukka boots is perfect for weekends at the lake or everyday rambling. With a handsewn moccasin construction and easy to care for soft and smooth leather upper, these boots feature Eastland exclusive Active Memory Foam comfort insole, that supports and conforms to the curves of your foot, while the shock absorbing, flexible natural rubber outsole offers durability and traction. Boot height: 3 1/4”. Heel height: 5/8”. Material: Leather, Memory Foam, Rubber.

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SeaVees Men’s 3 Eye Chukka Boot,Shadow Blue,8.5 M US

Oiled suede Seavees chukka boots. The traditional 3-eye design is a relaxed boot that’s not too casual. Leather upper on an EVA sole.

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Timberland TB06666A231 Men’s Skhigh Rock II Boot Wheat Nubuck 8.5 W US

Hit the trails with the Timberland 6666A Skhigh Rock II Boots! These boots have premium leather and Cordura nylon uppers for rugged durability and a durable outsole made from 42% recycled rubber for traction and durability.

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Kenneth Cole New York Men’s Totaled Chelsea Boot, Black, 8.5 M US

Providing the fashion world with style these Total-Ed Kenneth Cole shoes are great for any occasion The low heel and closed toe give you both elegance and comfort There is no compromising style comfort or function These shoes by Kenneth Cole are a perfect fit

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Sebago Men’s Rutland Chelsea Boot, Black, 8.5 M US

It’s easy to be the man about town in footwear with effortless, modern panache. This classic and easy slip on Chelsea boot in premium leathers has a look that’s traditional yet feels elegant with exquisite linings, cushioning comfort and lightweight construction. The slip-resistant outsole protects while the waterproof Sebago Drysides construction keeps you dry in rainy and slushy conditions.

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Kenneth Cole REACTION Men’s Hit Men Lace-Up Boot,Brown Leather,8.5 M US

Men’s Kenneth Cole Reaction, Hit Man Combat style fashion Boot Leather and manmade upper in a cap toe combat styled boot Lace up design with dual side zip closure Fabric and manmade lining Lightly cushioned insole 6 inch boot shaft with 4 inch opening 1 ? inch heel Manmade outsole. Heel Height of 1.25 inches

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Justin Boots Men’s U.S.A. Bent Rail Collection 11″ Boot Wide Square Double Stitch Toe Leather Outsole,Tan Road,8.5 D US

Introducing the Justin Bent Rail cowboy boot collection, inspired by alternative country and an outlaw attitude This rugged cowboy boot features a distressed and burnished leather foot under a matching 11″ leather shaft. Leather lining. Leather covered cushion insole and triple density insole board. 1 3/8″ sanded longbase block heel. Double stitched welt. Smooth leather sole. Wide square toe and easy-on pull straps.

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MARC NEW YORK Men’s Stanton Chukka Boot,Silverfox/Gum,8.5 D US

Highlight any Marco’s style with this vintage inspired Chukka boot. A true gentlemen’s boot, the Stanton chukka features a heavy waxy upper with leather trim, waxy laces with an extra second color lace and a durable outsole.

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Old West Men’s Trucker Western Work Boot Distressed 8.5 D(M) US

With a nod to its hardworking and frugal western heritage, this cowboy boot is as tough as it is affordable. Old West work boot features a genuine leather foot and matching 13″ fancy stitched leather shaft. Manmade lining. Medium toe and cowboy heel.