Shop High Ankle Shoes Men

Sponsored
$149.00
L.L.Bean | Men's Storm Chaser 5 Chelsea Boots Oakwood 9.5 M(D), Leather/Rubber/Nylon
L.L.Bean
Free shipping
$149.00
L.L.Bean | Men's Storm Chaser 5 Chelsea Boots Oakwood 9.5 M(D), Leather/Rubber/Nylon
L.L.Bean
Free shipping
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Classic Black 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Classic Black 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$139.00
L.L.Bean | Men's Stonington Chelsea Boots, Leather Dark Oakwood 14 M(D), Leather/Rubber
L.L.Bean
Free shipping
$139.00
L.L.Bean | Men's Stonington Chelsea Boots, Leather Dark Oakwood 14 M(D), Leather/Rubber
L.L.Bean
Free shipping
$169.95
Ariat Men's Groundbreaker Chelsea Waterproof Work Boots - Steel Toe
Boot Barn
1K+
$169.95
Ariat Men's Groundbreaker Chelsea Waterproof Work Boots - Steel Toe
Boot Barn
1K+
$159.95
Ariat Men's Midtown Rambler Stone Chelsea Boots - Square Toe
Boot Barn
5K+
$159.95
Ariat Men's Midtown Rambler Stone Chelsea Boots - Square Toe
Boot Barn
5K+
$283.50
Men's 13" Old Brown Sheepskin Lined Snowshoe Lace Up Moccasin Boots
Leather-Moccasins
$283.50
Men's 13" Old Brown Sheepskin Lined Snowshoe Lace Up Moccasin Boots
Leather-Moccasins
$159.99
Best Boots For Calcaneal Spur, Hands Free, Premium Arch Support, Men's Leather Ankle Boots | Orthofeet Heel Pain Boots, Dalton, 9 / Medium / Brown
Orthofeet
$159.99
Best Boots For Calcaneal Spur, Hands Free, Premium Arch Support, Men's Leather Ankle Boots | Orthofeet Heel Pain Boots, Dalton, 9 / Medium / Brown
Orthofeet
$29.99
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
JCPenney
In store
13
Curbside
$29.99
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
JCPenney
13
$29.99
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 12, Brown
Kohl's
179
50% off
$29.99
$59.99
Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 12, Brown
Kohl's
179
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 8.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
20% Off*
$110.00
Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 8.0 | Red/Brown | Leather/Synthetic/Metal
Skechers USA
20% Off*
$66.00
$110.00
Clarks Mens Shacre Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Comfort
JCPenney
Free shipping
40% off
$66.00
$110.00
Clarks Mens Shacre Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Comfort
JCPenney
Free shipping
$1,195.00
Christian Louboutin Urbino Chelsea Black - Mens Shoes - Size 42
Christian Louboutin
Free shipping
$1,195.00
Christian Louboutin Urbino Chelsea Black - Mens Shoes - Size 42
Christian Louboutin
Free shipping
$107.20
$160.00
UGG Men's Captrail High Top Waterproof Sneakers, Mens, 13, Black
Dillard's
33% off
$107.20
$160.00
UGG Men's Captrail High Top Waterproof Sneakers, Mens, 13, Black
Dillard's
$29.99
$90.00
St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 13 | Boots Lace Up Boots | Memory Foam
JCPenney
In store
Curbside
$29.99
$90.00
St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 13 | Boots Lace Up Boots | Memory Foam
JCPenney
$49.99
$79.99
Deer Stags Rockland Men's Chelsea Boots, Size: 11.5, Brown Dark Brown
Kohl's
6K+
Free shipping
37% off
$49.99
$79.99
Deer Stags Rockland Men's Chelsea Boots, Size: 11.5, Brown Dark Brown
Kohl's
6K+
$114.95
Propet Men's Blizzard Ankle Zip Boots In Brown/Black, Size 10, M(D) | Ames Walker
AmesWalker
1
$114.95
Propet Men's Blizzard Ankle Zip Boots In Brown/Black, Size 10, M(D) | Ames Walker
AmesWalker
1
$89.99
Heydude Mens Bradley Boot Men's Brown Size 11m | Rack Room Shoes
Rack Room Shoes
$89.99
Heydude Mens Bradley Boot Men's Brown Size 11m | Rack Room Shoes
Rack Room Shoes
$149.95
Ariat Men's Booker Ultra Bantamweight Chukka Boots - Square Toe
Boot Barn
618
$149.95
Ariat Men's Booker Ultra Bantamweight Chukka Boots - Square Toe
Boot Barn
618
$1,295.00
Christian Louboutin Samson Black - Mens Shoes - Size 41
Christian Louboutin
Free shipping
$1,295.00
Christian Louboutin Samson Black - Mens Shoes - Size 41
Christian Louboutin
Free shipping
$985.00
Tecovas Men's The Dean Zip Boots, Round Toe, 8" Shaft, Black Cherry, Crocodile, 1.25" Heel, 9.5 D
Tecovas
1
$985.00
Tecovas Men's The Dean Zip Boots, Round Toe, 8" Shaft, Black Cherry, Crocodile, 1.25" Heel, 9.5 D
Tecovas
1
$49.99
$60.00
Deer Stags Bangor Men's Chukka Boots, Size: 8, Black
Kohl's
43
Free shipping
16% off
$49.99
$60.00
Deer Stags Bangor Men's Chukka Boots, Size: 8, Black
Kohl's
43
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 8.5 | Black | Leather/Synthetic
Skechers USA
20% Off*
$105.00
Skechers Men's Relaxed Fit: Respected - Boswell Boots | Size 8.5 | Black | Leather/Synthetic
Skechers USA
20% Off*
$167.50
Men's Earthing Ankle Moccasin Boots With Native Indian Braid For Sale
Healthy & Grounded
$167.50
Men's Earthing Ankle Moccasin Boots With Native Indian Braid For Sale
Healthy & Grounded
$66.98
$89.99
HEYDUDE Bradley Classic Casual Boots For Men - Charcoal - 10m
Cabela's
In store
25% off
$66.98
$89.99
HEYDUDE Bradley Classic Casual Boots For Men - Charcoal - 10m
Cabela's
$119.96
UGG Neumel Chukka Boot | Men's | Grey | Size 10 | Boots
DSW
$10 Off*
Free shipping
$119.96
UGG Neumel Chukka Boot | Men's | Grey | Size 10 | Boots
DSW
$10 Off*
$145.50
Men's Cork Brown Laurentian Chief Apache Ankle Moccasin Boots
Leather-Moccasins
$145.50
Men's Cork Brown Laurentian Chief Apache Ankle Moccasin Boots
Leather-Moccasins
$89.00
$259.00
Rothy's - Men's Chelsea Boot In Black, Size 10
Rothy's.com
65% off
$89.00
$259.00
Rothy's - Men's Chelsea Boot In Black, Size 10
Rothy's.com
$66.98
$89.99
HEYDUDE Bradley Classic Casual Boots For Men - Walnut - 11m
Cabela's
In store
25% off
$66.98
$89.99
HEYDUDE Bradley Classic Casual Boots For Men - Walnut - 11m
Cabela's
$150.00
UGG® Men's Biltmore Chelsea Leather Cold Weather Boots In Black/, Size 10.5
Ugg
2K+
$150.00
UGG® Men's Biltmore Chelsea Leather Cold Weather Boots In Black/, Size 10.5
Ugg
2K+
$78.99
$105.00
Skechers Men's Work: Relaxed Fit - Workshire ST Boots | Size 8.5 | Black | Leather/Synthetic
Skechers USA
24% off
$78.99
$105.00
Skechers Men's Work: Relaxed Fit - Workshire ST Boots | Size 8.5 | Black | Leather/Synthetic
Skechers USA
$53.74
$79.22
Shoes For Men, Mens Shoes, Men's Solid Pointed Toe High Heel Boots With Belt Buckle Decor, Stylish Boots For, Mens High Heeled Boots,Mens Boots
Temu US
37
32% off
$53.74
$79.22
Shoes For Men, Mens Shoes, Men's Solid Pointed Toe High Heel Boots With Belt Buckle Decor, Stylish Boots For, Mens High Heeled Boots,Mens Boots
Temu US
37
$150.00
UGG® Men's Biltmore Chelsea Leather Cold Weather Boots In Brown/, Size 10.5
Ugg
1K+
$150.00
UGG® Men's Biltmore Chelsea Leather Cold Weather Boots In Brown/, Size 10.5
Ugg
1K+
$99.95
Caterpillar Men's Threshold Chukka Boot Black, Size 10m
CATFootwear.com
$99.95
Caterpillar Men's Threshold Chukka Boot Black, Size 10m
CATFootwear.com
$69.99
$89.99
HEYDUDE Men's Bradley Boots Brown, 10 - Men's Casual At Academy Sports
Academy Sports + Outdoors
22% off
$69.99
$89.99
HEYDUDE Men's Bradley Boots Brown, 10 - Men's Casual At Academy Sports
Academy Sports + Outdoors
$74.99
$99.95
Caterpillar Men's Threshold Chukka Boot Beaned, Size 13m
CATFootwear.com
24% off
$74.99
$99.95
Caterpillar Men's Threshold Chukka Boot Beaned, Size 13m
CATFootwear.com
$111.99
$160.00
UGG® Men's Captrail High Suede/Textile/Recycled Materials Sneakers In Black, Size 11
Ugg
30% off
$111.99
$160.00
UGG® Men's Captrail High Suede/Textile/Recycled Materials Sneakers In Black, Size 11
Ugg
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    Shop High Ankle Shoes Men

    Sponsored
    $149.00
    L.L.Bean | Men's Storm Chaser 5 Chelsea Boots Oakwood 9.5 M(D), Leather/Rubber/Nylon
    L.L.Bean
    Free shipping
    $149.00
    L.L.Bean | Men's Storm Chaser 5 Chelsea Boots Oakwood 9.5 M(D), Leather/Rubber/Nylon
    L.L.Bean
    Free shipping
    $169.00
    L.L.Bean | Men's Portland Boots, Chelsea Classic Black 11 M(D), Leather/Rubber
    L.L.Bean
    Free shipping
    $169.00
    L.L.Bean | Men's Portland Boots, Chelsea Classic Black 11 M(D), Leather/Rubber
    L.L.Bean
    Free shipping
    $139.00
    L.L.Bean | Men's Stonington Chelsea Boots, Leather Dark Oakwood 14 M(D), Leather/Rubber
    L.L.Bean
    Free shipping
    $139.00
    L.L.Bean | Men's Stonington Chelsea Boots, Leather Dark Oakwood 14 M(D), Leather/Rubber
    L.L.Bean
    Free shipping
    $169.95
    Ariat Men's Groundbreaker Chelsea Waterproof Work Boots - Steel Toe
    Boot Barn
    1K+
    $169.95
    Ariat Men's Groundbreaker Chelsea Waterproof Work Boots - Steel Toe
    Boot Barn
    1K+
    $159.95
    Ariat Men's Midtown Rambler Stone Chelsea Boots - Square Toe
    Boot Barn
    5K+
    $159.95
    Ariat Men's Midtown Rambler Stone Chelsea Boots - Square Toe
    Boot Barn
    5K+
    $283.50
    Men's 13" Old Brown Sheepskin Lined Snowshoe Lace Up Moccasin Boots
    Leather-Moccasins
    $283.50
    Men's 13" Old Brown Sheepskin Lined Snowshoe Lace Up Moccasin Boots
    Leather-Moccasins
    $159.99
    Best Boots For Calcaneal Spur, Hands Free, Premium Arch Support, Men's Leather Ankle Boots | Orthofeet Heel Pain Boots, Dalton, 9 / Medium / Brown
    Orthofeet
    $159.99
    Best Boots For Calcaneal Spur, Hands Free, Premium Arch Support, Men's Leather Ankle Boots | Orthofeet Heel Pain Boots, Dalton, 9 / Medium / Brown
    Orthofeet
    $29.99
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
    JCPenney
    In store
    13
    Curbside
    $29.99
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
    JCPenney
    13
    $29.99
    $59.99
    Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 12, Brown
    Kohl's
    179
    50% off
    $29.99
    $59.99
    Sonoma Goods For Life® Ledger Men's Chukka Boots, Size: 12, Brown
    Kohl's
    179
    $110.00
    Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 8.0 | Red/Brown | Leather/Synthetic/Metal
    Skechers USA
    20% Off*
    $110.00
    Skechers Men's Hands Free Slip-Ins Relaxed Fit: Pollard - Waylon Boots | Size 8.0 | Red/Brown | Leather/Synthetic/Metal
    Skechers USA
    20% Off*
    $66.00
    $110.00
    Clarks Mens Shacre Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Comfort
    JCPenney
    Free shipping
    40% off
    $66.00
    $110.00
    Clarks Mens Shacre Flat Heel Chukka Boots | Brown | Regular 10 1/2 | Boots Chukka Boots | Comfort
    JCPenney
    Free shipping
    $1,195.00
    Christian Louboutin Urbino Chelsea Black - Mens Shoes - Size 42
    Christian Louboutin
    Free shipping
    $1,195.00
    Christian Louboutin Urbino Chelsea Black - Mens Shoes - Size 42
    Christian Louboutin
    Free shipping
    $107.20
    $160.00
    UGG Men's Captrail High Top Waterproof Sneakers, Mens, 13, Black
    Dillard's
    33% off
    $107.20
    $160.00
    UGG Men's Captrail High Top Waterproof Sneakers, Mens, 13, Black
    Dillard's
    $29.99
    $90.00
    St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 13 | Boots Lace Up Boots | Memory Foam
    JCPenney
    In store
    Curbside
    $29.99
    $90.00
    St. John's Bay Mens Hatley Flat Heel Lace Up Boots | Black | Regular 13 | Boots Lace Up Boots | Memory Foam
    JCPenney
    $49.99
    $79.99
    Deer Stags Rockland Men's Chelsea Boots, Size: 11.5, Brown Dark Brown
    Kohl's
    6K+
    Free shipping
    37% off
    $49.99
    $79.99
    Deer Stags Rockland Men's Chelsea Boots, Size: 11.5, Brown Dark Brown
    Kohl's
    6K+
    $114.95
    Propet Men's Blizzard Ankle Zip Boots In Brown/Black, Size 10, M(D) | Ames Walker
    AmesWalker
    1
    $114.95
    Propet Men's Blizzard Ankle Zip Boots In Brown/Black, Size 10, M(D) | Ames Walker
    AmesWalker
    1
    $89.99
    Heydude Mens Bradley Boot Men's Brown Size 11m | Rack Room Shoes
    Rack Room Shoes
    $89.99
    Heydude Mens Bradley Boot Men's Brown Size 11m | Rack Room Shoes
    Rack Room Shoes
    $149.95
    Ariat Men's Booker Ultra Bantamweight Chukka Boots - Square Toe
    Boot Barn
    618
    $149.95
    Ariat Men's Booker Ultra Bantamweight Chukka Boots - Square Toe
    Boot Barn
    618