Shop Ankle Length Boots Fashion Men

Sponsored
$259.99
Men's Red Wing® Weekender Chelsea Boots | Copper | Size 9 | Leather
Orvis
Special Offer
$259.99
Men's Red Wing® Weekender Chelsea Boots | Copper | Size 9 | Leather
Orvis
Special Offer
$1,900.00
Hermès - Hike Ankle Boot, Men's, Leather, Black
Hermès
Free shipping
$1,900.00
Hermès - Hike Ankle Boot, Men's, Leather, Black
Hermès
Free shipping
$1,650.00
Hermès - John Ankle Boot, Men's, Leather, Black
Hermès
Free shipping
$1,650.00
Hermès - John Ankle Boot, Men's, Leather, Black
Hermès
Free shipping
$176.00
$220.00
Men's Barbour® Farsley Leather Chelsea Boots | Black | Size 12
Orvis
Special Offer
20% off
$176.00
$220.00
Men's Barbour® Farsley Leather Chelsea Boots | Black | Size 12
Orvis
Special Offer
$2,150.00
Hermès - Veo Ankle Boot, Men's, Leather, Black
Hermès
Free shipping
$2,150.00
Hermès - Veo Ankle Boot, Men's, Leather, Black
Hermès
Free shipping
$2,150.00
Hermès - Jeff Ankle Boot, Men's, Leather, Beige/Natural
Hermès
Free shipping
$2,150.00
Hermès - Jeff Ankle Boot, Men's, Leather, Beige/Natural
Hermès
Free shipping
$176.00
$220.00
Men's Barbour® Farsley Leather Chelsea Boots | Khaki | Size 10
Orvis
Special Offer
20% off
$176.00
$220.00
Men's Barbour® Farsley Leather Chelsea Boots | Khaki | Size 10
Orvis
Special Offer
$159.95
Dunham Men's Cloud Plus Waterproof Mid Boot 2 Ankle Breen Nubuck 13 X-Wide
Amazon.com
96
Free shipping
$159.95
Dunham Men's Cloud Plus Waterproof Mid Boot 2 Ankle Breen Nubuck 13 X-Wide
Amazon.com
96
$48.74
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 9 | Boots Chelsea Boots | Memory Foam | Valentine's Day
JCPenney
In store
15
Curbside
$48.74
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 9 | Boots Chelsea Boots | Memory Foam | Valentine's Day
JCPenney
15
$49.00
$144.99
Durango Men's Black Harness Boot - 11 Inch Tall - Khaki, 7.5
tohittheroad.com
66% off
$49.00
$144.99
Durango Men's Black Harness Boot - 11 Inch Tall - Khaki, 7.5
tohittheroad.com
$295.00
Tecovas Men's The Chance Boots, Round Toe, 6" Shaft, Brandy, Cowhide, 1.25" Heel, 10 D
Tecovas
1
$295.00
Tecovas Men's The Chance Boots, Round Toe, 6" Shaft, Brandy, Cowhide, 1.25" Heel, 10 D
Tecovas
1
$198.00
Ralph Lauren Bryson Suede Chelsea Boot - Size 12 in Brown
Ralph Lauren
16
$198.00
Ralph Lauren Bryson Suede Chelsea Boot - Size 12 in Brown
Ralph Lauren
16
$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
$115.00
Skechers Men's Hands Free Slip-Ins Waterproof Relaxed Fit: Respected - Ivar Boots | Size 7.5 | Black/Brown | Leather/Synthetic/Textile
Skechers USA
20% Off*
$115.00
Skechers Men's Hands Free Slip-Ins Waterproof Relaxed Fit: Respected - Ivar Boots | Size 7.5 | Black/Brown | Leather/Synthetic/Textile
Skechers USA
20% Off*
$139.99
$198.00
Ralph Lauren Ranger Mid Color-Blocked Suede Boot - Size 10.5 in Colorblock
Ralph Lauren
5
29% off
$139.99
$198.00
Ralph Lauren Ranger Mid Color-Blocked Suede Boot - Size 10.5 in Colorblock
Ralph Lauren
5
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 9.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
20% Off*
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 9.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
20% Off*
$295.00
Tecovas Men's The Dean Zip Boots, Round Toe, 8" Shaft, Scotch, Goat, 1.25" Heel, 10.5 D
Tecovas
$295.00
Tecovas Men's The Dean Zip Boots, Round Toe, 8" Shaft, Scotch, Goat, 1.25" Heel, 10.5 D
Tecovas
$225.00
Tecovas Men's The Rugged Chelsea, Light Tobacco, Cowhide, Size 12
Tecovas
1
$225.00
Tecovas Men's The Rugged Chelsea, Light Tobacco, Cowhide, Size 12
Tecovas
1
$159.99
$228.00
Ralph Lauren Bryson Leather & Wool Cap-Toe Boot - Size 8.5 in Polo Pale Russet/Black
Ralph Lauren
46
29% off
$159.99
$228.00
Ralph Lauren Bryson Leather & Wool Cap-Toe Boot - Size 8.5 in Polo Pale Russet/Black
Ralph Lauren
46
$33.29
$90.00
St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 8 1/2 | Boots Lace Up Boots | Memory Foam | Valentine's Day
JCPenney
In store
Curbside
$33.29
$90.00
St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 8 1/2 | Boots Lace Up Boots | Memory Foam | Valentine's Day
JCPenney
$139.99
$198.00
Ralph Lauren Ranger Tumbled Leather Boot - Size 10 in Polo Tan
Ralph Lauren
78
29% off
$139.99
$198.00
Ralph Lauren Ranger Tumbled Leather Boot - Size 10 in Polo Tan
Ralph Lauren
78
$36.09
2023 Men's Medieval Knee High Boots Cross Strap Lace Up Shoes Flat Cool Moto Boots Tall Renaissance Boots Fall Winter - 12, Brown
reinsho.com
$36.09
2023 Men's Medieval Knee High Boots Cross Strap Lace Up Shoes Flat Cool Moto Boots Tall Renaissance Boots Fall Winter - 12, Brown
reinsho.com
$48.74
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 12 | Boots Chukka Boots | Memory Foam
JCPenney
In store
Curbside
$48.74
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Black | Regular 12 | Boots Chukka Boots | Memory Foam
JCPenney
$48.74
$90.00
St. John's Bay Mens Brock Block Heel Lace Up Boots | Brown | Regular 8 1/2 | Boots Lace Up Boots | Lug Sole|Memory Foam
JCPenney
24
45% off
$48.74
$90.00
St. John's Bay Mens Brock Block Heel Lace Up Boots | Brown | Regular 8 1/2 | Boots Lace Up Boots | Lug Sole|Memory Foam
JCPenney
24
$174.99
$248.00
Ralph Lauren Logan Leather Chelsea Boot - Size 7 in Black
Ralph Lauren
29% off
$174.99
$248.00
Ralph Lauren Logan Leather Chelsea Boot - Size 7 in Black
Ralph Lauren
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 8.0 | Black | Leather/Synthetic/Metal
Skechers USA
20% Off*
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 8.0 | Black | Leather/Synthetic/Metal
Skechers USA
20% Off*
$48.74
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
45% off
$48.74
$90.00
St. John's Bay Mens Mills Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Memory Foam
JCPenney
$128.00
Ralph Lauren Talan Suede Chukka Boot - Size 13 in Desert Tan
Ralph Lauren
$128.00
Ralph Lauren Talan Suede Chukka Boot - Size 13 in Desert Tan
Ralph Lauren
$129.95
Propet Men's Cliff Walker Tall Strap Boots In Black, Size 14, M(D) | Ames Walker
AmesWalker
800
$129.95
Propet Men's Cliff Walker Tall Strap Boots In Black, Size 14, M(D) | Ames Walker
AmesWalker
800
$38.49
$90.00
Dockers Mens Durham Flat Heel Chelsea Boots | Brown | Regular 10 1/2 | Boots Chelsea Boots | Comfort
JCPenney
57% off
$38.49
$90.00
Dockers Mens Durham Flat Heel Chelsea Boots | Brown | Regular 10 1/2 | Boots Chelsea Boots | Comfort
JCPenney
$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
5K+
$94.71
Propét Men's Blizzard Mid Zip-M Hiking Boot
Amazon.com
2
Free shipping
$94.71
Propét Men's Blizzard Mid Zip-M Hiking Boot
Amazon.com
2
$159.99
$228.00
Ralph Lauren Bryson Leather Cap-Toe Boot - Size 7 in Dark Brown
Ralph Lauren
29% off
$159.99
$228.00
Ralph Lauren Bryson Leather Cap-Toe Boot - Size 7 in Dark Brown
Ralph Lauren
$35.99
$90.00
Mutual Weave Mens Freeport Flat Heel Lace Up Boots | Black | Regular 13 | Boots Lace Up Boots | Memory Foam
JCPenney
In store
Curbside
$35.99
$90.00
Mutual Weave Mens Freeport Flat Heel Lace Up Boots | Black | Regular 13 | Boots Lace Up Boots | Memory Foam
JCPenney
$285.00
Tecovas Men's The Knox Roper Boots, Round Toe, 10" Shaft, Briar, Cowhide, 1" Heel, 12 D
Tecovas
1
$285.00
Tecovas Men's The Knox Roper Boots, Round Toe, 10" Shaft, Briar, Cowhide, 1" Heel, 12 D
Tecovas
1
$45.49
$130.00
Clarks Mens Burchill Up Flat Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Comfort
JCPenney
65% off
$45.49
$130.00
Clarks Mens Burchill Up Flat Heel Chelsea Boots | Brown | Regular 13 | Boots Chelsea Boots | Comfort
JCPenney
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    Shop Ankle Length Boots Fashion Men

    Sponsored
    $259.99
    Men's Red Wing® Weekender Chelsea Boots | Copper | Size 9 | Leather
    Orvis
    Special Offer
    $259.99
    Men's Red Wing® Weekender Chelsea Boots | Copper | Size 9 | Leather
    Orvis
    Special Offer
    $1,900.00
    Hermès - Hike Ankle Boot, Men's, Leather, Black
    Hermès
    Free shipping
    $1,900.00
    Hermès - Hike Ankle Boot, Men's, Leather, Black
    Hermès
    Free shipping
    $1,650.00
    Hermès - John Ankle Boot, Men's, Leather, Black
    Hermès
    Free shipping
    $1,650.00
    Hermès - John Ankle Boot, Men's, Leather, Black
    Hermès
    Free shipping
    $176.00
    $220.00
    Men's Barbour® Farsley Leather Chelsea Boots | Black | Size 12
    Orvis
    Special Offer
    20% off
    $176.00
    $220.00
    Men's Barbour® Farsley Leather Chelsea Boots | Black | Size 12
    Orvis
    Special Offer
    $2,150.00
    Hermès - Veo Ankle Boot, Men's, Leather, Black
    Hermès
    Free shipping
    $2,150.00
    Hermès - Veo Ankle Boot, Men's, Leather, Black
    Hermès
    Free shipping
    $2,150.00
    Hermès - Jeff Ankle Boot, Men's, Leather, Beige/Natural
    Hermès
    Free shipping
    $2,150.00
    Hermès - Jeff Ankle Boot, Men's, Leather, Beige/Natural
    Hermès
    Free shipping
    $176.00
    $220.00
    Men's Barbour® Farsley Leather Chelsea Boots | Khaki | Size 10
    Orvis
    Special Offer
    20% off
    $176.00
    $220.00
    Men's Barbour® Farsley Leather Chelsea Boots | Khaki | Size 10
    Orvis
    Special Offer
    $159.95
    Dunham Men's Cloud Plus Waterproof Mid Boot 2 Ankle Breen Nubuck 13 X-Wide
    Amazon.com
    96
    Free shipping
    $159.95
    Dunham Men's Cloud Plus Waterproof Mid Boot 2 Ankle Breen Nubuck 13 X-Wide
    Amazon.com
    96
    $48.74
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 9 | Boots Chelsea Boots | Memory Foam | Valentine's Day
    JCPenney
    In store
    15
    Curbside
    $48.74
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 9 | Boots Chelsea Boots | Memory Foam | Valentine's Day
    JCPenney
    15
    $49.00
    $144.99
    Durango Men's Black Harness Boot - 11 Inch Tall - Khaki, 7.5
    tohittheroad.com
    66% off
    $49.00
    $144.99
    Durango Men's Black Harness Boot - 11 Inch Tall - Khaki, 7.5
    tohittheroad.com
    $295.00
    Tecovas Men's The Chance Boots, Round Toe, 6" Shaft, Brandy, Cowhide, 1.25" Heel, 10 D
    Tecovas
    1
    $295.00
    Tecovas Men's The Chance Boots, Round Toe, 6" Shaft, Brandy, Cowhide, 1.25" Heel, 10 D
    Tecovas
    1
    $198.00
    Ralph Lauren Bryson Suede Chelsea Boot - Size 12 in Brown
    Ralph Lauren
    16
    $198.00
    Ralph Lauren Bryson Suede Chelsea Boot - Size 12 in Brown
    Ralph Lauren
    16
    $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
    $115.00
    Skechers Men's Hands Free Slip-Ins Waterproof Relaxed Fit: Respected - Ivar Boots | Size 7.5 | Black/Brown | Leather/Synthetic/Textile
    Skechers USA
    20% Off*
    $115.00
    Skechers Men's Hands Free Slip-Ins Waterproof Relaxed Fit: Respected - Ivar Boots | Size 7.5 | Black/Brown | Leather/Synthetic/Textile
    Skechers USA
    20% Off*
    $139.99
    $198.00
    Ralph Lauren Ranger Mid Color-Blocked Suede Boot - Size 10.5 in Colorblock
    Ralph Lauren
    5
    29% off
    $139.99
    $198.00
    Ralph Lauren Ranger Mid Color-Blocked Suede Boot - Size 10.5 in Colorblock
    Ralph Lauren
    5
    $110.00
    Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 9.0 | Red/Brown | Leather/Synthetic/Metal
    Skechers USA
    20% Off*
    $110.00
    Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 9.0 | Red/Brown | Leather/Synthetic/Metal
    Skechers USA
    20% Off*
    $295.00
    Tecovas Men's The Dean Zip Boots, Round Toe, 8" Shaft, Scotch, Goat, 1.25" Heel, 10.5 D
    Tecovas
    $295.00
    Tecovas Men's The Dean Zip Boots, Round Toe, 8" Shaft, Scotch, Goat, 1.25" Heel, 10.5 D
    Tecovas
    $225.00
    Tecovas Men's The Rugged Chelsea, Light Tobacco, Cowhide, Size 12
    Tecovas
    1
    $225.00
    Tecovas Men's The Rugged Chelsea, Light Tobacco, Cowhide, Size 12
    Tecovas
    1

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