Men's Chelsea Boots

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Solo
$119.99 $24.99

Pair these Chelsea boots with a leather biker jacket, plain white tee, and distressed jeans to create a look great for casual outi...ngs Size: 10. Color: Brown. Gender: Male. Age Group: Adult. read more

Solo
$119.99 $24.99

Pair these Chelsea boots with a leather biker jacket, plain white tee, and distressed jeans to create a look great for casual outi...ngs Size: 11. Color: Black. Gender: Male. Age Group: Adult. read more

Vincent Cavallo
$120.00 $29.99

Create an upscale, modern look with this chelsea and Monk Strap dress boot. Available in rich organic hues and comfort features su...ch as slip-resistant outsoles and padded insoles. A stylish addition to any formal or casual wear. Size: 8.5. Color:... read more

Deer Stags
$79.95

Look sleek and cool with Deer Stags Award updated Chelsea Boot. Synthetic and leather upper Twin gore paneling for a secure fit.

Frye
$298.00

Frye Men's Sam Leather Chelsea Boots. This sleek ankle boot pairs perfectly with tailored, straight leg jeans or slacks. Crafted f...rom leather, this durable pair will take you from season to season with style! read more

Bed|Stu
$245.00 $79.97

Sizing: True to size. Round toe. Topstitching. Dual elastic side gores. Pull-on. Padded insole. Approx. 3" shaft height, 13.5" ope...ning circumference. Imported read more

Vionic with Orthaheel Technology
$189.95

The Vionic with Orthaheel Technology Kingsley Chelsea Boot is a timeless style favorite, with twin gore panels for comfort and an ...ankle-high silhouette. This chelsea boot's sophisticated detailing gives it a polished vibe. Genuine leather-skinned... read more

Georgia Boot
$119.95

*With an emphasis on comfort and performance, the Georgia Boot® Blue Collar Chelsea Waterproof Work Pull-On Boot is ready to suppo...rt you through hard work *Full-grain leather upper with elastic goring and front and back pull tabs *5" shaft height... read more

Dr. Martens
$135.00 $79.97

Sizing: True to size. Whole sizes only; for 1/2 sizes, order next size up. Round toe. Technical knit construction. Lace-up. Memory... foam insole. Approx. 6" shaft height. Imported read more

Solo
$119.99 $24.99

Pair these Chelsea boots with a leather biker jacket, plain white tee, and distressed jeans to create a look great for casual outi...ngs Size: 9.5. Color: Blue. Gender: Male. Age Group: Adult. read more

Bearpaw
$69.99 $59.99

The Bearpaw Marcus Chelsea Boot combines a classic silhouette with NeverWet™ water-repelling technology and a soft cushioned footb...ed. Cow suede, classic construction, twin-gore silhouette Treated with NeverWet™ water-repelling technology Wool blend... read more

Dr. Martens
$165.00 $89.97

Sizing: True to size. Whole sizes only; for 1/2 sizes, order next size up. Round toe. Dual elastic side gores. Pull-on. Lightly pa...dded insole. Back pull loop. Goodyear Welt detail. Air cushioned sole. Approx. 6" shaft height, 11" opening circumference.... read more

Franco Vanucci
$160.00 $41.99

Add some fashion to your wardrobe with these dress boots. The ankle boots will keep you moving in style and are the perfect additi...on to your boot collection! Size: 8.5. Color: Brown. Gender: Male. Age Group: Adult. read more

Lucky Brand
$119.95

The Lucky Brand Men's Buck Chelsea Boot has pitch-perfect construction that makes it comfortable enough for everyday wear. With ge...nuine leather uppers in heritage styling, it looks great with every ensemble. Twin gore Lug sole Heel pull tab. read more

Dr. Martens
$135.00 $79.97

With its strong silhouette and low-key, working class style, Pascal epitomizes the earliest offerings produced by Dr. Martens in t...he 1960s and embraced by youth culture from Liverpool to San Francisco. Celebrating that heritage, we've chosen to craft... read more

Groupon Goods
$84.99 $49.99

Pair these Chelsea boots with a shirt, bomber jacket, and slacks to create a semi-formal casual or office look Size: 9. Color: Blu...e. Gender: Male. Age Group: Adult. read more

Naot
$205.95

The Business Chelsea Boot is classically good looking. It'll look great whether you're in with jeans or slacks. The attractive lea...ther upper has a rounded toe and double elastic insets, for easy on and off, as well as a comfortable fit. The removable... read more

Dr. Martens
$110.00 $59.97

Sizing: True to size. Whole sizes only; for half sizes, size down. Round cap toe. Contrasting leather construction. Lace-up with s...ide zip closure. Lightly padded insole. Back pull loop. Welting detail. Air cushioned sole. Approx. 6" shaft height. Imported read more

Groupon Goods
$84.99 $49.99

Pair these Chelsea boots with a shirt, bomber jacket, and slacks to create a semi-formal casual or office look Size: 11. Color: Gr...ey. Gender: Male. Age Group: Adult. read more

Lucky Brand
$119.95

The Lucky Brand Men's Hutchins Chelsea Boot has pitch-perfect construction that makes it comfortable enough for everyday wear. Wit...h genuine leather uppers in heritage styling, it looks great with every ensemble. Twin gore Lug sole Mixed material upper. read more

Dr. Martens
$80.00 $44.97

Sizing: True to size. Whole sizes only; for 1/2 sizes, order next size up. Round toe. Topstitching. Canvas construction. Lace-up. ...Lightly padded insole. Back pull loop. Imported read more

Franco Vanucci
$160.00 $41.99

Add some fashion to your wardrobe with these dress boots. The ankle boots will keep you moving in style and are the perfect additi...on to your boot collection! Size: 8.5. Color: Brown. Gender: Male. Age Group: Adult. read more

Lucky Brand
$119.95

The Lucky Brand Men's Buck Chelsea Boot has pitch-perfect construction that makes it comfortable enough for everyday wear. With ge...nuine leather uppers in heritage styling, it looks great with every ensemble. Twin gore Lug sole Heel pull tab. read more

Dr. Martens
$140.00 $79.97

Sizing: True to size. Whole sizes only; for 1/2 sizes, order next size up. Round toe. Lace-up. Lightly padded insole. Back pull lo...op. Goodyear Welt. Air cushioned sole. Approx. 6" shaft height. Imported read more

Franco Vanucci
$160.00 $41.99

Add some fashion to your wardrobe with these dress boots. The ankle boots will keep you moving in style and are the perfect additi...on to your boot collection! Size: 9.5. Color: Black. Gender: Male. Age Group: Adult. read more

Lucky Brand
$119.95

The Lucky Brand Men's Hutchins Chelsea Boot has pitch-perfect construction that makes it comfortable enough for everyday wear. Wit...h genuine leather uppers in heritage styling, it looks great with every ensemble. Twin gore Lug sole Mixed material upper. read more

Dr. Martens
$135.00 $79.97

Sizing: True to size. Whole sizes only; for 1/2 sizes, order next size up. Round toe. Technical knit construction. Lace-up. Memory... foam insole. Approx. 6" shaft height. Imported read more

Groupon Goods
$80.00 $64.99

These men's Chelsea boots by Vance Co feature faux suede uppers that rise to the ankles with stretchy fabric on the outside of eac...h shoe. Top-stitching detail adds to the appearance and faux woodgrain outsoles and block heels finish the design Size: 8.... read more

Dr. Martens
$139.95

This utilitarian Dr. Martens 2976 Chelsea boot feels so fresh and modern with its leather upper, easy side elastic gore, branded p...ull tab and Chelsea silhouette you almost forget its historical beginnings as a equestrian and farming shoe. Durable... read more

Dr. Martens
$90.00 $54.97

The Combs 8-eye unisex boot was created to withstand anything. with serious style. Made with a military-esque waxed canvas, the Co...mbs is a fold-down style that's rugged and durable yet lightweight. The canvas boot serves up all the classic Doc's DNA... read more

Sperry Top-Sider
$149.95

*Cooler days call for this versatile chukka boot's comfortable, casual style *Premium leather upper with rugged stitch-out constru...ction *Twin elastic side panels for easy slip-on wear *Removable molded EVA footbed *Shock-absorbing EVA midsole... read more

Zanzara
$240.00 $76.80

Apron toe. Lace-up vamp closure. Topstitch detail. Midsole with ridge detail. Lightly padded footbed. Grip sole. Approx. 6" shaft ...height. Imported read more

Dr. Martens
$80.00 $44.97

Sizing: True to size. Whole sizes only; for half sizes, size down. Round toe. Lace-up vamp. Padded collar with pull-tab. Goodyear-...welt construction. Grip sole. Approx. 4" shaft height. Imported read more

$24.37

As Is reason: Various Reasons Option: Black - 10 Miko Lotti Men's Chelsea Boots: Slip-on design, leather lining for comfort, Man-M...ade Upper, Leather Lining, Rubber Sole, Fits true to size, Burnished toe detail Measurement Guide Men's Shoe Sizing Guide... read more

Rush By Gordon Rush
$155.00 $79.97

Sizing: True to size. Round toe. Gore insets. Pull-on. Back pull-tab. Lightly padded footbed. Stitched welt midsole. Approx. 5" sh...aft height, 11" opening circumference. Imported read more

Dr. Martens
$100.00 $59.97

Sizing: True to size. Whole sizes only; for half sizes, size down. Plain toe. Geo embossed leather. Synthetic nubuck details. Lace...-up style. Lightly cushioned insole. Padded shaft. Back pull tab. Contrasting welt stitching. Grip sole. Approx. 6" shaft... read more

Georgia Boot
$149.95

*With an emphasis on comfort and performance, the Georgia Boot® Blue Collar Chelsea Waterproof Work Pull-On Boot is ready to suppo...rt you through hard work *Full-grain leather upper *10" shaft height *High-performance breathable moisture-wicking mesh... read more

Johnston & Murphy
$175.00 $99.97

Sizing: True to size. Round toe. Brogued detail. Stretchy gore insets for easy on/offs and flexible fit. Pull-on. Padded footbed. ...Stitched welt midsole for durability. Grip sole for traction. Approx. 5" shaft height, 12" opening circumference. Imported read more

Dr. Martens
$90.00 $54.97

Sizing: True to size. Whole sizes only; for half sizes, size down. Plain toe. Lace-up. Lightly cushioned insole. Back pull tab. Co...ntrasting welt stitching. Grip sole. Approx. 6" shaft height. Imported read more

Kenneth Cole Reaction
$97.95

*Take on the town in style with this handsome Chelsea boot *Full-grain leather upper *Dual elastic side gores for easy slip-on wea...r *Cushioned footbed *Man-made sole read more

Mezlan
$450.00 $207.92

Sizing: True to size. Almond toe. Topstitched welt. Suede construction. Aide zip closure. Stacked mini lug grip sole. Approx. 6" s...haft height, 11" opening circumference. ImportedThis item cannot be shipped to Delaware. read more

Dr. Martens
$140.00 $79.97

Sizing: True to size. Whole sizes only; for 1/2 sizes, order next size down. Round toe. Lace-up. Lightly padded insole. Goodyear w...elt. Air cushioned lug sole. Approx. 6.5" shaft height. Imported read more

Steve Madden
$99.95

*This sleek Chelsea boot is a smart choice for all-around wear *Leather upper with subtle perfed accents at sides *Side elastic go...res for easy slip-on wear *Lightly cushioned footbed *Flexible rubber-like sole read more

Johnston & Murphy
$198.00 $95.04

A sturdy lug sole grounds a full-grain leather boot finished with an all-around welt and a touch of broguing.Sizing: True to size.... Round cap toe. Brogued detail. Lace-up style. Padded collar and footbed. Stitched welt midsole for durability. Grip lug... read more

Dr. Martens
$90.00 $49.97

Sizing: True to size. Whole sizes only; for half sizes, size down. Plain toe. Khaki construction. Lace-up. Lightly cushioned insol...e. Back pull tab. Contrasting welt stitching. Grip sole. Approx. 6" shaft height. Imported read more

Kenneth Cole Reaction
$97.95 $48.99

*Take on the town in style with this handsome Chelsea boot *Full-grain leather upper *Dual elastic side gores for easy slip-on wea...r *Cushioned footbed *Man-made sole read more

ECCO
$175.00 $109.97

Supple leather construction defines a modern derby shaped in a clean-cut silhouette. Sizing: True to size. Whole sizes only; for 1.../2 sizes, order next size up. Reference size chart for European conversion. Round toe. Lace-up vamp. Leather construction.... read more

Dr. Martens
$100.00 $59.97

Sizing: True to size. Whole sizes only; for half sizes, size down. Plain toe. Geo embossed leather. Synthetic nubuck details. Lace...-up style. Lightly cushioned insole. Padded shaft. Back pull tab. Contrasting welt stitching. Grip sole. Approx. 6" shaft... read more

Wolverine Heritage
$255.95

*A new take on the classic Chelsea style boot, the Wolverine Cromwell is made for every day *Rich full-grain leather or suede uppe...r *Leather lined *Lightly cushioned footbed *Rubber midsole softens steps *Vibram ® lug outsole for reliable and superior... read more

Harley Davidson
$149.99 $79.97

A mens leather boot, with classic urban work styling. The Candler shares an iconic silhouette, and a reliable Goodyear welted cons...truction for a life as tough as it looks.Sizing: True to size. Round moc toe. Harley Davidson logo hardware. Lace-up... read more

Dr. Martens
$100.00 $59.97

Sizing: True to size. Whole sizes only; for half sizes, size down. Plain toe. Geo embossed leather. Synthetic nubuck details. Lace...-up style. Lightly cushioned insole. Padded shaft. Back pull tab. Contrasting welt stitching. Grip sole. Approx. 6" shaft... read more

Deer Stags
$79.95

*Look sleek and cool with Deer Stags Award updated Chelsea boot *Synthetic leather upper with classic pull-on styling *Lightly cus...hioned insole read more