Shop Ankle Boots Chelsea for Men

Sponsored
$39.99
Jousen Men's Chelsea Boots Lightweight Casual Chukka Ankle Boots Classic Elastic Dress Boots For Men
Amazon.com
Free shipping
$39.99
Jousen Men's Chelsea Boots Lightweight Casual Chukka Ankle Boots Classic Elastic Dress Boots For Men
Amazon.com
$119.97
$180.00
Men's Leather Dress Chelsea Shoe Chestnut Regular Size 10 1/2
Banana Republic Factory
33% off
$119.97
$180.00
Men's Leather Dress Chelsea Shoe Chestnut Regular Size 10 1/2
Banana Republic Factory
$49.99
Moretti Men's Wylie Chelsea Boots Clearance At Jos. A. Bank, Black, Size 10 D Width - Shoes
Jos. A. Bank Clothiers, Inc.
$49.99
Moretti Men's Wylie Chelsea Boots Clearance At Jos. A. Bank, Black, Size 10 D Width - Shoes
Jos. A. Bank Clothiers, Inc.
$43.99
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
JCPenney
In store
20
Curbside
$43.99
$90.00
St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
JCPenney
$59.99
Mix No. 6 Aleder Chelsea Boot | Men's | Black | Size 12 | Boots
DSW
$59.99
Mix No. 6 Aleder Chelsea Boot | Men's | Black | Size 12 | Boots
DSW
$80.00
$100.00
J. Ferrar Mens Blake Flat Heel Chelsea Boots | Black | Regular 12 | Boots Chelsea Boots | Memory Foam
JCPenney
In store
30
Free shipping
Curbside
$80.00
$100.00
J. Ferrar Mens Blake Flat Heel Chelsea Boots | Black | Regular 12 | Boots Chelsea Boots | Memory Foam
JCPenney
$112.95
Wolverine Men's Floorhand Romeo Steel Toe Waterproof Chelsea Boot
Amazon.com
2
Free shipping
$112.95
Wolverine Men's Floorhand Romeo Steel Toe Waterproof Chelsea Boot
Amazon.com
$225.00
Tecovas Men's The Rugged Chelsea Boots, Pavement, Roughout, Size 10, D-Average
Tecovas
Special Offer
$225.00
Tecovas Men's The Rugged Chelsea Boots, Pavement, Roughout, Size 10, D-Average
Tecovas
$51.90
Nunn Bush Men's Excursion Moccasin Toe Slip-On Water Resistant Pull On Boot Chelsea
Amazon.com
14
Free shipping
$51.90
Nunn Bush Men's Excursion Moccasin Toe Slip-On Water Resistant Pull On Boot Chelsea
Amazon.com
$114.00
$190.00
Fitflop | Men's MARGAN Waterproof Leather Chelsea Boots, Outlet, Chocolate, Size: US 10
FitFlop Official Shop
40% off
$114.00
$190.00
Fitflop | Men's MARGAN Waterproof Leather Chelsea Boots, Outlet, Chocolate, Size: US 10
FitFlop Official Shop
$34.99
$90.00
Deer Stags Men's Rockland Memory Foam Chelsea Boot - Brown - Size 11.5m
Macy's
Special Offer
61% off
$34.99
$90.00
Deer Stags Men's Rockland Memory Foam Chelsea Boot - Brown - Size 11.5m
Macy's
$26.95
$49.00
Men's Huxley Chelsea Boots - Goodfellow & Co Black 10.5: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
Target
Free shipping
45% off
$26.95
$49.00
Men's Huxley Chelsea Boots - Goodfellow & Co Black 10.5: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
Target
$79.99
Deer Stags Rockland Men's Chelsea Boots, Size: 12, Brown Dark Brown
Kohl's
Special Offer
Free shipping
$79.99
Deer Stags Rockland Men's Chelsea Boots, Size: 12, Brown Dark Brown
Kohl's
$225.00
Tecovas Men's The Rugged Chelsea Boots, Light Tobacco, Cowhide, Size 8, D-Average
Tecovas
Special Offer
$225.00
Tecovas Men's The Rugged Chelsea Boots, Light Tobacco, Cowhide, Size 8, D-Average
Tecovas
$60.00
$75.00
Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots
JCPenney
6K+
20% off
$60.00
$75.00
Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots
JCPenney
$41.99
$69.99
Alfani Men's Luka 2 Pull-On Chelsea Boots, Created For Macy's - Cognac - Size 10
Macy's
Special Offer
40% off
$41.99
$69.99
Alfani Men's Luka 2 Pull-On Chelsea Boots, Created For Macy's - Cognac - Size 10
Macy's
$97.76
Sale-Timberland Larchmont Ii Leather Textile Mens Chelsea Boots - Saddle , UK 11 | US 11.5 Men | EU 45.5 , Medium
Lakerrealty Sports Store
$97.76
Sale-Timberland Larchmont Ii Leather Textile Mens Chelsea Boots - Saddle , UK 11 | US 11.5 Men | EU 45.5 , Medium
Lakerrealty Sports Store
$26.95
$49.00
Men's Huxley Chelsea Boots - Goodfellow & Co Brown 13: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
Target
Free shipping
45% off
$26.95
$49.00
Men's Huxley Chelsea Boots - Goodfellow & Co Brown 13: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
Target
$139.99
Florsheim Men's Rucci Chelsea Boots (Black Leather) - Size 10.0 m
Famous Footwear
7
Free shipping
$139.99
Florsheim Men's Rucci Chelsea Boots (Black Leather) - Size 10.0 m
Famous Footwear
$199.95
Rustic Brown Premium Leather Chelsea Boots Men's Style 585, Size 10 Blundstone
Blundstone
4K+
$199.95
Rustic Brown Premium Leather Chelsea Boots Men's Style 585, Size 10 Blundstone
Blundstone
$139.99
Florsheim Men's Rucci Chelsea Boots (Cognac Leather) - Size 10.5 m
Famous Footwear
Free shipping
$139.99
Florsheim Men's Rucci Chelsea Boots (Cognac Leather) - Size 10.5 m
Famous Footwear
$54.00
$90.00
Madden Men Men's Maxxin Mid Height Chelsea Boot - Black - Size 11.5
Macy's
Special Offer
Free shipping
40% off
$54.00
$90.00
Madden Men Men's Maxxin Mid Height Chelsea Boot - Black - Size 11.5
Macy's
$42.99
$60.57
Men's Brown Faux Leather Chelsea Boots - Stylish Slip-On Ankle Boots With Rugged Tread And Perforated Detailing
LightInTheBox
29% off
$42.99
$60.57
Men's Brown Faux Leather Chelsea Boots - Stylish Slip-On Ankle Boots With Rugged Tread And Perforated Detailing
LightInTheBox
$69.99
$89.99
Deer Stags Men's Rockland Chelsea Boots (Redwood/Dark Brown) - Size 11.5 m
Famous Footwear
3K+
22% off
$69.99
$89.99
Deer Stags Men's Rockland Chelsea Boots (Redwood/Dark Brown) - Size 11.5 m
Famous Footwear
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
Free shipping
$169.00
L.L.Bean | Men's Portland Boots, Chelsea Dark Russet 11 M(D), Leather/Rubber
L.L.Bean
$79.99
Deer Stags Rockland Men's Chelsea Boots, Size: 8 Wide, Black Black
Kohl's
Special Offer
Free shipping
$79.99
Deer Stags Rockland Men's Chelsea Boots, Size: 8 Wide, Black Black
Kohl's
$1,390.00
Mcqueen Men's Leather Chelsea Boots, Black, Men's, 9D, Boots Chelsea Boots
Neiman Marcus
Free shipping
$1,390.00
Mcqueen Men's Leather Chelsea Boots, Black, Men's, 9D, Boots Chelsea Boots
Neiman Marcus
$38.50
$55.00
Men's Spencer Winter Chelsea Boots - Goodfellow & Co Brown 11: Pull-On, Treaded Outsole, Leather Upper
Target
Free shipping
30% off
$38.50
$55.00
Men's Spencer Winter Chelsea Boots - Goodfellow & Co Brown 11: Pull-On, Treaded Outsole, Leather Upper
Target
$209.95
Rustic Brown / Mustard-Black Premium Leather Chelsea Boots Men's Style 1944 , Size 8.5 Blundstone
Blundstone
4K+
$209.95
Rustic Brown / Mustard-Black Premium Leather Chelsea Boots Men's Style 1944 , Size 8.5 Blundstone
Blundstone
$59.99
Mix No. 6 Aleder Chelsea Boot | Men's | Dark Brown | Size 12 | Boots
DSW
$59.99
Mix No. 6 Aleder Chelsea Boot | Men's | Dark Brown | Size 12 | Boots
DSW
$290.00
$580.00
SANDRO Glazed Leather Chelsea Boots In Black At Nordstrom, Size 45
Nordstrom
50% off
$290.00
$580.00
SANDRO Glazed Leather Chelsea Boots In Black At Nordstrom, Size 45
Nordstrom
$140.00
UGG® Men's Neumel Chelsea Suede Classic Boots In Chestnut, Size 7
Ugg
415
$140.00
UGG® Men's Neumel Chelsea Suede Classic Boots In Chestnut, Size 7
Ugg
$124.99
Mens Eastland Norway Chelsea Ankle Boots 12 D Black | Boscov's
Boscov's
$124.99
Mens Eastland Norway Chelsea Ankle Boots 12 D Black | Boscov's
Boscov's
$149.96
Steve Madden Aben Chelsea Boot | Men's | Black | Size 12 | Boots
DSW
6
Free shipping
$149.96
Steve Madden Aben Chelsea Boot | Men's | Black | Size 12 | Boots
DSW
$199.95
Black Full Grain Leather Chelsea Boots Men's Style 063, Size 10.5 Blundstone
Blundstone
1K+
$199.95
Black Full Grain Leather Chelsea Boots Men's Style 063, Size 10.5 Blundstone
Blundstone
$65.00
Deer Stags Brayden Men's Dress Chelsea Boots, Size: 9.5, Brown
Kohl's
Special Offer
Free shipping
$65.00
Deer Stags Brayden Men's Dress Chelsea Boots, Size: 9.5, Brown
Kohl's
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    Shop Ankle Boots Chelsea for Men

    Sponsored
    $39.99
    Jousen Men's Chelsea Boots Lightweight Casual Chukka Ankle Boots Classic Elastic Dress Boots For Men
    Amazon.com
    Free shipping
    $39.99
    Jousen Men's Chelsea Boots Lightweight Casual Chukka Ankle Boots Classic Elastic Dress Boots For Men
    Amazon.com
    $119.97
    $180.00
    Men's Leather Dress Chelsea Shoe Chestnut Regular Size 10 1/2
    Banana Republic Factory
    33% off
    $119.97
    $180.00
    Men's Leather Dress Chelsea Shoe Chestnut Regular Size 10 1/2
    Banana Republic Factory
    $49.99
    Moretti Men's Wylie Chelsea Boots Clearance At Jos. A. Bank, Black, Size 10 D Width - Shoes
    Jos. A. Bank Clothiers, Inc.
    $49.99
    Moretti Men's Wylie Chelsea Boots Clearance At Jos. A. Bank, Black, Size 10 D Width - Shoes
    Jos. A. Bank Clothiers, Inc.
    $43.99
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
    JCPenney
    In store
    20
    Curbside
    $43.99
    $90.00
    St. John's Bay Mens Rutland Flat Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots | Memory Foam
    JCPenney
    $59.99
    Mix No. 6 Aleder Chelsea Boot | Men's | Black | Size 12 | Boots
    DSW
    $59.99
    Mix No. 6 Aleder Chelsea Boot | Men's | Black | Size 12 | Boots
    DSW
    $80.00
    $100.00
    J. Ferrar Mens Blake Flat Heel Chelsea Boots | Black | Regular 12 | Boots Chelsea Boots | Memory Foam
    JCPenney
    In store
    30
    Free shipping
    Curbside
    $80.00
    $100.00
    J. Ferrar Mens Blake Flat Heel Chelsea Boots | Black | Regular 12 | Boots Chelsea Boots | Memory Foam
    JCPenney
    $112.95
    Wolverine Men's Floorhand Romeo Steel Toe Waterproof Chelsea Boot
    Amazon.com
    2
    Free shipping
    $112.95
    Wolverine Men's Floorhand Romeo Steel Toe Waterproof Chelsea Boot
    Amazon.com
    $225.00
    Tecovas Men's The Rugged Chelsea Boots, Pavement, Roughout, Size 10, D-Average
    Tecovas
    Special Offer
    $225.00
    Tecovas Men's The Rugged Chelsea Boots, Pavement, Roughout, Size 10, D-Average
    Tecovas
    $51.90
    Nunn Bush Men's Excursion Moccasin Toe Slip-On Water Resistant Pull On Boot Chelsea
    Amazon.com
    14
    Free shipping
    $51.90
    Nunn Bush Men's Excursion Moccasin Toe Slip-On Water Resistant Pull On Boot Chelsea
    Amazon.com
    $114.00
    $190.00
    Fitflop | Men's MARGAN Waterproof Leather Chelsea Boots, Outlet, Chocolate, Size: US 10
    FitFlop Official Shop
    40% off
    $114.00
    $190.00
    Fitflop | Men's MARGAN Waterproof Leather Chelsea Boots, Outlet, Chocolate, Size: US 10
    FitFlop Official Shop
    $34.99
    $90.00
    Deer Stags Men's Rockland Memory Foam Chelsea Boot - Brown - Size 11.5m
    Macy's
    Special Offer
    61% off
    $34.99
    $90.00
    Deer Stags Men's Rockland Memory Foam Chelsea Boot - Brown - Size 11.5m
    Macy's
    $26.95
    $49.00
    Men's Huxley Chelsea Boots - Goodfellow & Co Black 10.5: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
    Target
    Free shipping
    45% off
    $26.95
    $49.00
    Men's Huxley Chelsea Boots - Goodfellow & Co Black 10.5: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
    Target
    $79.99
    Deer Stags Rockland Men's Chelsea Boots, Size: 12, Brown Dark Brown
    Kohl's
    Special Offer
    Free shipping
    $79.99
    Deer Stags Rockland Men's Chelsea Boots, Size: 12, Brown Dark Brown
    Kohl's
    $225.00
    Tecovas Men's The Rugged Chelsea Boots, Light Tobacco, Cowhide, Size 8, D-Average
    Tecovas
    Special Offer
    $225.00
    Tecovas Men's The Rugged Chelsea Boots, Light Tobacco, Cowhide, Size 8, D-Average
    Tecovas
    $60.00
    $75.00
    Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots
    JCPenney
    6K+
    20% off
    $60.00
    $75.00
    Deer Stags Mens Rockland Block Heel Chelsea Boots | Brown | Regular 12 | Boots Chelsea Boots
    JCPenney
    $41.99
    $69.99
    Alfani Men's Luka 2 Pull-On Chelsea Boots, Created For Macy's - Cognac - Size 10
    Macy's
    Special Offer
    40% off
    $41.99
    $69.99
    Alfani Men's Luka 2 Pull-On Chelsea Boots, Created For Macy's - Cognac - Size 10
    Macy's
    $97.76
    Sale-Timberland Larchmont Ii Leather Textile Mens Chelsea Boots - Saddle , UK 11 | US 11.5 Men | EU 45.5 , Medium
    Lakerrealty Sports Store
    $97.76
    Sale-Timberland Larchmont Ii Leather Textile Mens Chelsea Boots - Saddle , UK 11 | US 11.5 Men | EU 45.5 , Medium
    Lakerrealty Sports Store
    $26.95
    $49.00
    Men's Huxley Chelsea Boots - Goodfellow & Co Brown 13: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
    Target
    Free shipping
    45% off
    $26.95
    $49.00
    Men's Huxley Chelsea Boots - Goodfellow & Co Brown 13: Faux Leather, Pull-On, Cushioned Insole, Non-Marking Outsole
    Target

    • Top Chelsea Men's Boots (2025) | The Winner is Clear

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