Men's Chelsea Boots

🔥 Top Men's Chelsea Boots Deals for 2025 you shouldn’t miss!

Never miss out on the good deals!

Jousen Chelsea Boots Men Leather Casual Retro Slip On Boots Elastic Fashion Ankle Boots for Men (AMY8141 Brown 12)

$49.99

Great

Lowest

View at Amazon

Jousen Chelsea Boots Men Leather Casual Retro Slip On Boots Elastic Fashion Ankle Boots for Men(AMY8141A Tan 9.5)

-12% $69.99

Great

Lowest

View at Amazon

Jousen Chelsea Boots Casual Slip On Ankle Waterproof Mens Boots(AMY8119A black 15)

$59.99

Great

Lowest

View at Amazon

Jousen Chelsea Boots Casual Slip On Ankle Waterproof Mens Boots(AMY8119A brown 14)

$59.99

Great

Lowest

View at Amazon

Jousen Chelsea Boots Casual Slip On Ankle Waterproof Mens Boots(AMY8119A blackpu 10)

-6% $55.99

Great

Lowest

View at Amazon

UGG Men's Classic Slip-On Boot, Chestnut, 14

$109.95

Great

Lowest

View at Amazon

lezzglt saltwater waterproof high performance gardening

Lezzglt Mens Deck Boots, Saltwater Fishing Booties Rubber Waterproof Ankle Rain Boots, High-performance Footwear Chelsea Boots for Gardening Fishing Boating Camping Sailing

-14% $29.99

Great

Lowest

View at Amazon

Lezzglt Mens Deck Boots, Saltwater Fishing Booties Rubber Waterproof Ankle Rain Boots, High-performance Footwear Chelsea Boots for Gardening Fishing Boating Camping Sailing

-14% $29.99

Great

Lowest

View at Amazon

Lezzglt Mens Deck Boots, Saltwater Fishing Booties Rubber Waterproof Ankle Rain Boots, High-performance Footwear Chelsea Boots for Gardening Fishing Boating Camping Sailing

-14% $29.99

Great

Lowest

View at Amazon

Skechers Men's Segment-Dorton Boot, Dark Brown, 8 XW US

-5% $82.99

Great

Lowest

View at Amazon

UGG Men's Classic Slip-On Boot, Chestnut, 15

$109.95

Great

Lowest

View at Amazon

Skechers Men's Segment-Dorton Boot, Dark Brown, 11 XW US

-2% $82.99

Great

Lowest

View at Amazon

Skechers Men's Segment-Dorton Boot, Black, 13 XW US

$82.99

Great

Lowest

View at Amazon

Skechers Men's Resment Korver Boot, Black/Black, 10 XW US

-1% $79.00

Great

Lowest

View at Amazon

Skechers Men's Resment Korver Boot, Black/Black, 10.5 XW US

$79.00

Great

Lowest

View at Amazon

Skechers Men's Resment Korver Boot, Black/Black, 8.5 XW US

-0% $79.00

Great

Lowest

View at Amazon

Skechers Men's RESMENT-Korver Chelsea Boot, Black/Black, 14 Medium US

$79.00

Great

Lowest

View at Amazon

Skechers Men's RESMENT-Korver Chelsea Boot, Black/Black, 9.5 Medium US

-1% $79.00

Great

Lowest

View at Amazon

Skechers Men's RESMENT-Korver Chelsea Boot, Black/Black, 8 Medium US

$79.00

Great

Lowest

View at Amazon

Skechers Men's RESMENT-Korver Chelsea Boot, Black/Black, 13 Medium US

-1% $79.00

Great

Lowest

View at Amazon

Skechers Men's Resment Korver Boot, Black/Black, 9.5 XW US

$79.00

Great

Lowest

View at Amazon

Skechers Men's RESMENT-Korver Chelsea Boot, Black/Black, 10 Medium US

-1% $79.00

Great

Lowest

View at Amazon

Skechers Men's Segment-Dorton Boot, Black, 12 XW US

$82.99

Great

Lowest

View at Amazon

Skechers Men's Segment-Dorton Boot, Dark Brown, 11.5 XW US

-1% $82.99

Great

Lowest

View at Amazon

Explore all products

UGG Men's Biltmore Chelsea Boot, Black, 15

-24% $112.50

Great

Lowest

View at Amazon

UGG Men's Biltmore Chelsea Boot, Black, 10.5

-21% $82.50

Great

Lowest

View at Amazon

Skechers Men's Segment-Dorton Boot, Dark Brown, 9.5 XW US

-2% $82.99

Great

Lowest

View at Amazon

UGG Men's Biltmore Chelsea Boot, Black, 11

-21% $82.50

Great

Lowest

View at Amazon

UGG Mens Biltmore Chelsea Boot, Black, 10 US

-21% $82.50

Great

Lowest

View at Amazon

UGG Men's Biltmore Chelsea Boot, Black, 11.5

-21% $82.50

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown Crazyhorse, 9.5 Medium

$109.95

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot, Cognac, 13 Wide

$109.95

Great

Lowest

View at Amazon

jousen chelsea lightweight classic elastic

Jousen Men's Chelsea Boots Leather Casual Mens Chukka Boots Retro Elastic Ankle Dress Boots for Men (AMY8154 Dark Brown 12)

$45.99

Great

Lowest

View at Amazon

Florsheim mens Medfield Plain Toe Zip Fashion Boot, Brown, 8.5 Wide US

-26% $90.41

Great

Lowest

View at Amazon

CGRRBW Brown Leather Chelsea Boots Men Dress Boots Ankle Slip on Boots Waterproof QEXXM02-BROWN-8

$56.99

Great

Lowest

View at Amazon

Arkbird Mens Hiking Boots, Stylish and Comfort Leather Chukka Ankle Boots Brown-7

-11% $79.99

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot, Cognac, 10 Medium

$109.95

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot, Cognac, 12 Wide

$109.95

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown Crazyhorse, 15 Medium

$109.95

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown Crazyhorse, 11 Medium

$109.95

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot Fashion, Brown Crazyhorse, 9 Wide

$109.95

Great

Lowest

View at Amazon

Florsheim Men's Medfield Plain Toe Zip Boot, Cognac, 15 Medium

$109.95

Great

Lowest

View at Amazon

Jousen Men's Chelsea Boots Leather Casual Men's Chukka Boots Retro Elastic Ankle Dress Boots for Men (AMY8154 Black 12)

-31% $42.99

Great

Lowest

View at Amazon

Jousen Chelsea Boots Men Square Toe Ankle Mens Western Boots Casual Slip On Boots for Men(AMY8421vine black 9)

$45.99

Great

Lowest

View at Amazon

Arkbird Mens Hiking Boots, Stylish and Comfort Leather Chukka Ankle Boots Brown-9.5

-10% $80.99

Great

Lowest

View at Amazon

Arkbird Mens Hiking Boots, Stylish and Comfort Leather Chukka Ankle Boots Brown-10

-10% $80.99

Great

Lowest

View at Amazon

Skechers Men's Segment-Dorton Boot, Dark Brown, 14 XW US

-2% $83.05

Great

View at Amazon

Skechers Men's Segment-Dorton Boot, Brown, 8 XW US

$79.95

Great

View at Amazon

1 2 3 4 5 6 7 18

Browse by related brands

Dr. Martens