Shop Men's Cuban Heel Ankle Boots

Sponsored
$119.99
$150.00
Most Comfortable Bunions Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Shoes, Ryder, 14 / Extra Wide / Brown
Orthofeet
20% off
$119.99
$150.00
Most Comfortable Bunions Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Shoes, Ryder, 14 / Extra Wide / Brown
Orthofeet
$129.99
$160.00
Orthopedic Diabetic Boots, Best Arch Support, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Shoes, Hunter, 9 / Extra Wide / Black
Orthofeet
18% off
$129.99
$160.00
Orthopedic Diabetic Boots, Best Arch Support, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Shoes, Hunter, 9 / Extra Wide / Black
Orthofeet
$119.99
$150.00
Doctor Recommended Standing All Day Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Highline, 11.5 / Medium / Black
Orthofeet
60-day returns (most items)
20% off
$119.99
$150.00
Doctor Recommended Standing All Day Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Highline, 11.5 / Medium / Black
Orthofeet
$119.99
$150.00
Most Comfortable Supportive Boots, Premium Arch Support, Superior Comfort & Protection, Men's Boots | Orthofeet Footwear, Ryder, 13 / Medium / Black
Orthofeet
20% off
$119.99
$150.00
Most Comfortable Supportive Boots, Premium Arch Support, Superior Comfort & Protection, Men's Boots | Orthofeet Footwear, Ryder, 13 / Medium / Black
Orthofeet
$124.99
$150.00
Podiatrist Recommended Walking And Standing Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Hunter, 10 / Wide / Brown
Orthofeet
16% off
$124.99
$150.00
Podiatrist Recommended Walking And Standing Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Hunter, 10 / Wide / Brown
Orthofeet
$259.99
Men's Red Wing® Weekender Chelsea Boots | Copper | Size 13 | Leather
Orvis
Special Offer
$259.99
Men's Red Wing® Weekender Chelsea Boots | Copper | Size 13 | Leather
Orvis
$109.99
$150.00
Most Comfortable Metatarsalgia Boots, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Footwear, Highline, 9 / Wide / Dark Brown
Orthofeet
26% off
$109.99
$150.00
Most Comfortable Metatarsalgia Boots, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Footwear, Highline, 9 / Wide / Dark Brown
Orthofeet
$149.95
Florsheim Men's, Norwalk Side Zip Boot Black Crazyhorse 10
Amazon.com
56
Free shipping
$149.95
Florsheim Men's, Norwalk Side Zip Boot Black Crazyhorse 10
Amazon.com
$155.99
BRUNT The Sullivan (Comp Toe), Dark Brown / 11
BRUNT Workwear
$155.99
BRUNT The Sullivan (Comp Toe), Dark Brown / 11
BRUNT Workwear
$139.99
$160.00
Orthopedic Boot For Sprained Ankle, Hands Free, Wide Toe Box Shoes, Arch Support Boots, Mens Boots | Orthofeet Chukka Boot, Verno, 11.5 / Wide / Black
Orthofeet
12% off
$139.99
$160.00
Orthopedic Boot For Sprained Ankle, Hands Free, Wide Toe Box Shoes, Arch Support Boots, Mens Boots | Orthofeet Chukka Boot, Verno, 11.5 / Wide / Black
Orthofeet
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Classic Black 13 M(D), Leather/Rubber
L.L.Bean
Free shipping
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Classic Black 13 M(D), Leather/Rubber
L.L.Bean
$179.00
L.L.Bean | Men's Portland Boots, Lace-Up Classic Black 13 M(D), Leather/Rubber
L.L.Bean
Free shipping
$179.00
L.L.Bean | Men's Portland Boots, Lace-Up Classic Black 13 M(D), Leather/Rubber
L.L.Bean
$48.74
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Memory Foam | Valentine's Day
JCPenney
In store
Curbside
$48.74
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Memory Foam | Valentine's Day
JCPenney
$63.02
Ellie Shoes Men's 158-Punk Combat Boot Brown M (10-11) Medium US
Amazon.com
Free shipping
$63.02
Ellie Shoes Men's 158-Punk Combat Boot Brown M (10-11) Medium US
Amazon.com
$198.00
Ralph Lauren Bryson Leather Chelsea Boot - Size 11.5 in Black
Ralph Lauren
$198.00
Ralph Lauren Bryson Leather Chelsea Boot - Size 11.5 in Black
Ralph Lauren
$199.00
L.L.Bean | Men's Bucksport Boots, Plain-Toe Black 11.5(EE), Leather/Rubber
L.L.Bean
Free shipping
$199.00
L.L.Bean | Men's Bucksport Boots, Plain-Toe Black 11.5(EE), Leather/Rubber
L.L.Bean
$56.24
$74.99
Vance Co Mens Landon Stacked Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Lightweight|Comfort
JCPenney
25% off
$56.24
$74.99
Vance Co Mens Landon Stacked Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Lightweight|Comfort
JCPenney
$115.94
ROPER Mens Horseshoe Kiltie Casual Boots Ankle - Brown 9
Amazon.com
Free shipping
$115.94
ROPER Mens Horseshoe Kiltie Casual Boots Ankle - Brown 9
Amazon.com
$450.00
Bruno Magli Men's Raging Side Zip Dress Boots - Black - Size 11
Bloomingdale's
Free shipping
$450.00
Bruno Magli Men's Raging Side Zip Dress Boots - Black - Size 11
Bloomingdale's
$139.00
L.L.Bean | Men's Stonington Chelsea Boots, Leather Dark Oakwood 7.5(EE), Leather/Rubber
L.L.Bean
Free shipping
$139.00
L.L.Bean | Men's Stonington Chelsea Boots, Leather Dark Oakwood 7.5(EE), Leather/Rubber
L.L.Bean
$88.38
ROPER Mens Clearcut Chukka Casual Boots Ankle - Brown Tan 12
Amazon.com
Free shipping
$88.38
ROPER Mens Clearcut Chukka Casual Boots Ankle - Brown Tan 12
Amazon.com
$179.00
Men's Portland Boots, Lace-Up Dark Russet 10 M(D), Leather/Rubber | L.L.Bean
L.L.Bean
Free shipping
$179.00
Men's Portland Boots, Lace-Up Dark Russet 10 M(D), Leather/Rubber | L.L.Bean
L.L.Bean
$103.16
Mens Real Leather Pointy Toe Cuban Heel Chelsea Ankle Boots Dress
eBay
Free shipping
$103.16
Mens Real Leather Pointy Toe Cuban Heel Chelsea Ankle Boots Dress
eBay
$99.95
Men's Sheepskin Cuffed Booties - Tan - 10 - The Vermont Country Store
Vermont Country Store
$99.95
Men's Sheepskin Cuffed Booties - Tan - 10 - The Vermont Country Store
Vermont Country Store
$79.99
Xti Men's Casual Ankle Boots - Brown - Size 10.5
Macy's
Free shipping
$79.99
Xti Men's Casual Ankle Boots - Brown - Size 10.5
Macy's
$209.95
$210.00
Vionic Livermore Men's Ankle Boot Black - 11.5 Medium
Orthotic Shop
$209.95
$210.00
Vionic Livermore Men's Ankle Boot Black - 11.5 Medium
Orthotic Shop
$209.95
$210.00
Vionic Livermore Men's Ankle Boot Dark Khaki - 9 Medium
Orthotic Shop
$209.95
$210.00
Vionic Livermore Men's Ankle Boot Dark Khaki - 9 Medium
Orthotic Shop
$108.00
Men's Florsheim Midtown Zip Boots, Black Medium
Belk
Free shipping
$108.00
Men's Florsheim Midtown Zip Boots, Black Medium
Belk
$113.98
British Mens Cuban High Heel Ankle Boots Formal Business Pointed Toe
eBay
Free shipping
$113.98
British Mens Cuban High Heel Ankle Boots Formal Business Pointed Toe
eBay
$129.95
Propet Men's Cliff Walker Tall Strap Boots In Black, Size 16, XX(5E) | Ames Walker
AmesWalker
$129.95
Propet Men's Cliff Walker Tall Strap Boots In Black, Size 16, XX(5E) | Ames Walker
AmesWalker
$48.74
$90.00
St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 10 | Boots Lace Up Boots | Memory Foam | Valentine's Day
JCPenney
In store
Curbside
$48.74
$90.00
St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 10 | Boots Lace Up Boots | Memory Foam | Valentine's Day
JCPenney
$209.95
$210.00
Vionic Livermore Men's Ankle Boot Tan - 11.5 Medium
Orthotic Shop
$209.95
$210.00
Vionic Livermore Men's Ankle Boot Tan - 11.5 Medium
Orthotic Shop
$56.25
$75.00
Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 10 1/2 | Boots Chelsea Boots
JCPenney
5K+
25% off
$56.25
$75.00
Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 10 1/2 | Boots Chelsea Boots
JCPenney
$199.95
Rustic Brown Premium Leather Chelsea Boots Men's Style 585, Size 9 Blundstone
Blundstone
Attractive Color · High-quality Material · Perfect Fit · Stylish · Value for Money
$199.95
Rustic Brown Premium Leather Chelsea Boots Men's Style 585, Size 9 Blundstone
Blundstone
$199.95
Men's Blundstone 550 Chelsea Boots Rustic Brown 7 M(D), Leather | L.L.Bean
L.L.Bean
Free shipping
365-day returns (most items)
$199.95
Men's Blundstone 550 Chelsea Boots Rustic Brown 7 M(D), Leather | L.L.Bean
L.L.Bean
$48.74
$90.00
St. John's Bay Mens Brock Block Heel Lace Up Boots | Brown | Regular 9 1/2 | Boots Lace Up Boots | Lug Sole|Memory Foam
JCPenney
In store
Curbside
$48.74
$90.00
St. John's Bay Mens Brock Block Heel Lace Up Boots | Brown | Regular 9 1/2 | Boots Lace Up Boots | Lug Sole|Memory Foam
JCPenney
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    Shop Men's Cuban Heel Ankle Boots

    Sponsored
    $119.99
    $150.00
    Most Comfortable Bunions Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Shoes, Ryder, 14 / Extra Wide / Brown
    Orthofeet
    20% off
    $119.99
    $150.00
    Most Comfortable Bunions Boots, Premium Arch Support, Ergonomic Sole, Men's Boots | Orthofeet Orthopedic Shoes, Ryder, 14 / Extra Wide / Brown
    Orthofeet
    $129.99
    $160.00
    Orthopedic Diabetic Boots, Best Arch Support, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Shoes, Hunter, 9 / Extra Wide / Black
    Orthofeet
    18% off
    $129.99
    $160.00
    Orthopedic Diabetic Boots, Best Arch Support, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Shoes, Hunter, 9 / Extra Wide / Black
    Orthofeet
    $119.99
    $150.00
    Doctor Recommended Standing All Day Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Highline, 11.5 / Medium / Black
    Orthofeet
    60-day returns (most items)
    20% off
    $119.99
    $150.00
    Doctor Recommended Standing All Day Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Highline, 11.5 / Medium / Black
    Orthofeet
    $119.99
    $150.00
    Most Comfortable Supportive Boots, Premium Arch Support, Superior Comfort & Protection, Men's Boots | Orthofeet Footwear, Ryder, 13 / Medium / Black
    Orthofeet
    20% off
    $119.99
    $150.00
    Most Comfortable Supportive Boots, Premium Arch Support, Superior Comfort & Protection, Men's Boots | Orthofeet Footwear, Ryder, 13 / Medium / Black
    Orthofeet
    $124.99
    $150.00
    Podiatrist Recommended Walking And Standing Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Hunter, 10 / Wide / Brown
    Orthofeet
    16% off
    $124.99
    $150.00
    Podiatrist Recommended Walking And Standing Boots, Enhanced Comfort, Men's Boots | Orthofeet Comfortable Footwear, Hunter, 10 / Wide / Brown
    Orthofeet
    $259.99
    Men's Red Wing® Weekender Chelsea Boots | Copper | Size 13 | Leather
    Orvis
    Special Offer
    $259.99
    Men's Red Wing® Weekender Chelsea Boots | Copper | Size 13 | Leather
    Orvis
    $109.99
    $150.00
    Most Comfortable Metatarsalgia Boots, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Footwear, Highline, 9 / Wide / Dark Brown
    Orthofeet
    26% off
    $109.99
    $150.00
    Most Comfortable Metatarsalgia Boots, Enhanced Comfort, Men's Boots | Orthofeet Orthopedic Footwear, Highline, 9 / Wide / Dark Brown
    Orthofeet
    $149.95
    Florsheim Men's, Norwalk Side Zip Boot Black Crazyhorse 10
    Amazon.com
    56
    Free shipping
    $149.95
    Florsheim Men's, Norwalk Side Zip Boot Black Crazyhorse 10
    Amazon.com
    $155.99
    BRUNT The Sullivan (Comp Toe), Dark Brown / 11
    BRUNT Workwear
    $155.99
    BRUNT The Sullivan (Comp Toe), Dark Brown / 11
    BRUNT Workwear
    $139.99
    $160.00
    Orthopedic Boot For Sprained Ankle, Hands Free, Wide Toe Box Shoes, Arch Support Boots, Mens Boots | Orthofeet Chukka Boot, Verno, 11.5 / Wide / Black
    Orthofeet
    12% off
    $139.99
    $160.00
    Orthopedic Boot For Sprained Ankle, Hands Free, Wide Toe Box Shoes, Arch Support Boots, Mens Boots | Orthofeet Chukka Boot, Verno, 11.5 / Wide / Black
    Orthofeet
    $169.00
    L.L.Bean | Men's Portland Boots, Chelsea Classic Black 13 M(D), Leather/Rubber
    L.L.Bean
    Free shipping
    $169.00
    L.L.Bean | Men's Portland Boots, Chelsea Classic Black 13 M(D), Leather/Rubber
    L.L.Bean
    $179.00
    L.L.Bean | Men's Portland Boots, Lace-Up Classic Black 13 M(D), Leather/Rubber
    L.L.Bean
    Free shipping
    $179.00
    L.L.Bean | Men's Portland Boots, Lace-Up Classic Black 13 M(D), Leather/Rubber
    L.L.Bean
    $48.74
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Memory Foam | Valentine's Day
    JCPenney
    In store
    Curbside
    $48.74
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Memory Foam | Valentine's Day
    JCPenney
    $63.02
    Ellie Shoes Men's 158-Punk Combat Boot Brown M (10-11) Medium US
    Amazon.com
    Free shipping
    $63.02
    Ellie Shoes Men's 158-Punk Combat Boot Brown M (10-11) Medium US
    Amazon.com
    $198.00
    Ralph Lauren Bryson Leather Chelsea Boot - Size 11.5 in Black
    Ralph Lauren
    $198.00
    Ralph Lauren Bryson Leather Chelsea Boot - Size 11.5 in Black
    Ralph Lauren
    $199.00
    L.L.Bean | Men's Bucksport Boots, Plain-Toe Black 11.5(EE), Leather/Rubber
    L.L.Bean
    Free shipping
    $199.00
    L.L.Bean | Men's Bucksport Boots, Plain-Toe Black 11.5(EE), Leather/Rubber
    L.L.Bean
    $56.24
    $74.99
    Vance Co Mens Landon Stacked Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Lightweight|Comfort
    JCPenney
    25% off
    $56.24
    $74.99
    Vance Co Mens Landon Stacked Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Lightweight|Comfort
    JCPenney
    $115.94
    ROPER Mens Horseshoe Kiltie Casual Boots Ankle - Brown 9
    Amazon.com
    Free shipping
    $115.94
    ROPER Mens Horseshoe Kiltie Casual Boots Ankle - Brown 9
    Amazon.com