Essential suede Chelsea boots from Urban Outfitters. Soft suede in a classic silhouette features elastic gusseting + heel tab for an easy on/off. Complete with a stacked heel and rubber... UO Suede Chelsea Boot

UO Suede Chelsea Boot

Urban Outfitters
$89.00
Essential suede Chelsea boots from Urban Outfitters. Soft suede in a classic silhouette features elastic gusseting + heel tab for an easy on/off. Complete with a stacked heel and rubber... UO Suede Chelsea Boot

UO Suede Chelsea Boot

Urban Outfitters
$89.00
Essential suede Chelsea boots from Urban Outfitters. Soft suede in a classic silhouette features elastic gusseting + heel tab for an easy on/off. Complete with a stacked heel and rubber... UO Suede Chelsea Boot

UO Suede Chelsea Boot

Urban Outfitters
$89.00
Saint Laurent’s Signature Wyatt 30 Jodhpur boots are a classic example of the Parisian label’s effortless ability to mix sleek elegance with a contemporary rock ’n’ roll twist. Presented... Saint Laurent Wyatt 30 Jodhpur Boots

Saint Laurent Wyatt 30 Jodhpur Boots

Browns Fashion
$1,045.00
The best value in all-weather footwear-PERIOD! 3.5mm neoprene liner makes this RedHead All-Season Classic II 5-Eye Lace-Up Insulated Boots lighter and more comfortable, while the rugged... RedHead All-Season Classic II 5-Eye Lace-Up Insulated Boots for Men - 9 M

RedHead All-Season Classic II 5-Eye...

Bass Pro Shops
RedHead
$59.99
A marvel of classic craftsmanship, the Wolverine 1000-Mile boot is constructed from Horween leather with the same heritage quality today as when it debuted in 1914. From Club Monaco Men's... Club Monaco Wolverine 1000 Mile Boot in Color Black

Club Monaco Wolverine 1000 Mile Boot...

Club Monaco
$355.00
A marvel of classic craftsmanship, the Wolverine 1000-Mile boot is constructed from Horween leather with the same heritage quality today as when it debuted in 1914. From Club Monaco Men's... Club Monaco Wolverine 1000 Mile Boot in Color Brown

Club Monaco Wolverine 1000 Mile Boot...

Club Monaco
$355.00
Since 1922, Allen Edmonds has been at the forefront of quality American craftsmanship, utilizing its trademark 212-step process to create long-wearing, world-class shoes from the best... Allen Edmonds Allen Edmonds Chelsea Boot in Color Black

Allen Edmonds Allen Edmonds Chelsea...

Club Monaco
$445.00
Brown heritage 6-inch classic moc toe leather boots. By Red Wing. Moccasin boot, water resistant leather, Goodyear welt construction, seven eyelets, crepe rubber traction tred outsole.... Brown Heritage 6-Inch Classic Moc Toe Leather Boots

Brown Heritage 6-Inch Classic Moc Toe...

Trouva
$238.00
Sizing: True to size. Round toe. Gore insets. Pull on. Back pull-tab. Memory foam padded footbed. Rubber bumper midsole. Grip sole. Approx. 5" shaft height, 11" opening circumference.... Steve Madden Equine Chelsea Boot - Men's Boots

Steve Madden Equine Chelsea Boot -...

Nordstrom Rack
Steve Madden
$100.00 $69.97

30%

Off
Sizing: True to size. Round toe. Gore insets. Pull on. Back pull-tab. Memory foam padded footbed. Rubber bumper midsole. Grip sole. Approx. 5" shaft height, 11" opening circumference.... Steve Madden Equine Chelsea Boot - Men's Boots

Steve Madden Equine Chelsea Boot -...

Nordstrom Rack
Steve Madden
$100.00 $69.97

30%

Off
Sizing: True to size. Round toe. Gore insets. Pull on. Back pull-tab. Memory foam padded footbed. Rubber bumper midsole. Grip sole. Approx. 5" shaft height, 11" opening circumference.... Steve Madden Equine Chelsea Boot - Men's Boots

Steve Madden Equine Chelsea Boot -...

Nordstrom Rack
Steve Madden
$100.00 $69.97

30%

Off
All the Storm Chaser features you love in our classic L.L.Bean Boot design. Fit best with midweight socks. For half sizes not offered, order up to next whole size. Waterproof, full-grain... Men's Storm Chasers Classic Waterproof Boots, Lace-Up

Men's Storm Chasers Classic...

L.L. Bean
L.L. Bean
$129.00
Free Shipping
The best value in all-weather footwear-PERIOD! 3.5mm neoprene liner makes this RedHead All-Season Classic II Insulated Pull-On Boot lighter and more comfortable, while the rugged suede... RedHead All-Season Classic II Insulated Pull-On Boots for Men - 13 M

RedHead All-Season Classic II...

Bass Pro Shops
RedHead
$59.99
RedWing shoes’ sturdy soles, premium leathers, triple stitching and Goodyear welt construction all work together to make quality boots that will last a lifetime. It takes more than 230... Redwing Classic Chukka Tan Ankle Boots Style 3140

Redwing Classic Chukka Tan Ankle...

Trouva
$199.00
Black classic monkey boots. Coming from the ‘Made in England’ core collection, this high shine leather boot is quintessentially English and an all-round classic. Made with a Goodyear welt,... Black Classic Monkey Boots

Black Classic Monkey Boots

Trouva
$199.00
Our popular all-weather Storm Chasers in a new L.L.Bean Boot-inspired design. Waterproof leather upper and exclusive TEK2.5 waterproof membrane protect from moisture. 200-gram PrimaLoft... Men's Storm Chasers Classic Waterproof Boots, Side-Zip

Men's Storm Chasers Classic...

L.L. Bean
L.L. Bean
$129.00
Free Shipping
All the Storm Chaser features you love in our classic L.L.Bean Boot design. Fit best with midweight socks. For half sizes not offered, order up to next whole size. Waterproof, full-grain... Men's Storm Chasers Classic Waterproof Boots, Lace-Up

Men's Storm Chasers Classic...

L.L. Bean
L.L. Bean
$129.00
Free Shipping
These men's Thorogood American Heritage work boots feature a safety-toe and a durable MAXwear outsole.Boot Technologies Safety toe meets Astm 2413-05 M/I/75/C/75 ratings Goodyear Storm welt... Thorogood American Heritage Classics Men's Mid-Calf Safety-Toe Work Boots

Thorogood American Heritage Classics...

Kohl's
$212.00
Get superior comfort and protection wearing these men's Thorogood American Heritage work boots.Boot Technologies Oil-tanned full-grain leather Steel toe meets Astm F2413-11 M/I/75/C/75... Thorogood American Heritage Classics Men's Steel-Toe Work Boots

Thorogood American Heritage Classics...

Kohl's
$254.00
Take on your tough jobs in the comfort and support of these men's American Heritage work boots from Thorogood.Boot Technologies Tobacco oil-tanned full-grain leather Meets Astm F2892-11... Thorogood American Heritage Classics Men's Leather Work Boots

Thorogood American Heritage Classics...

Kohl's
$238.00
Timberland Premium Waterproof boots. Classic Timberland boots crafted for women's feet, with colorful, rugged styling that can be dressed up with tights and dresses, or brought outside with... Timberland 6" Premium Waterproof Boots

Timberland 6" Premium Waterproof Boots

Tilly's
$169.99
Timberland Premium boots. Classic Timberland boots crafted for women's feet, with colorful, rugged styling that can be dressed up with tights and dresses, or brought outside with jeans and... Timberland 6" Premium Boots

Timberland 6" Premium Boots

Tilly's
$169.99 $127.49

25%

Off
Dr. Martens 8 eyelet 1460 boots. Smooth is the classic Dr. Martens leather durable, with a smooth finish. Dr. Martens air-cushion sole, oil and fat-resistant, offers good abrasion and slip... Dr. Martens 1460 Boots

Dr. Martens 1460 Boots

Tilly's
$134.99
Pair these boots with a plaid shirt, leather belt, straw hat, and regular-fit jeans to create a relaxed look with a cowboy vibe Size: 11. Color: Multi-Color. Gender: Male. Age Group: Adult. Men's Bonafini Men's Dress Boots: Walnut-Classic/11 Leather

Men's Bonafini Men's Dress Boots:...

Groupon
$80.00 $32.99

59%

Off
Pair these boots with a plaid shirt, leather belt, straw hat, and regular-fit jeans to create a relaxed look with a cowboy vibe Size: 8.5. Color: Black. Gender: Male. Age Group: Adult. Men's Bonafini Men's Dress Boots: Black-Classic/8.5 Black Leather

Men's Bonafini Men's Dress Boots:...

Groupon
$80.00 $32.99

59%

Off
The best value in all-weather footwear-PERIOD! 3.5mm neoprene liner makes this RedHead All-Season Classic II Insulated Pull-On Boot lighter and more comfortable, while the rugged suede... RedHead All-Season Classic II Insulated Pull-On Boots for Men - 9 M

RedHead All-Season Classic II...

Bass Pro Shops
RedHead
$59.99
Pair these boots with a plaid shirt, leather belt, straw hat, and regular-fit jeans to create a relaxed look with a cowboy vibe Size: 12. Color: Black. Gender: Male. Age Group: Adult. Men's Bonafini Men's Dress Boots: Black-Classic/12 Black Leather

Men's Bonafini Men's Dress Boots:...

Groupon
$80.00 $32.99

59%

Off
*This classic slip-on safety boot is water-resistant with a tough self-clearing sole, perfect when you need to work in wet or muddy conditions *Removable luxury footbed with arch support... Blundstone Foot TPU Stout Brown Boot

Blundstone Foot TPU Stout Brown Boot

ShoeMall.com
$159.95
Men's 8 Justin Classic Lace - R Western Boots Riding boots that work just as hard as you do. If you've ever owned a pair of Justin's world-famous, made-in-America workboots, they'll need no... Justin Boots Men's 8 inch Justin Classic Lace - R Boots, 9.5d, Black

Justin Boots Men's 8 inch Justin...

Sportsman's Guide
Justin
$138.99