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Main content
  1. Home
  2. Men
  3. Shoes
  4. Comfort
  5. Boots

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Comfort
  • Athletic
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Featured

  • Dress Shoes

Men's Comfort Boots

274 items
Product Image
Clarks®

Wallabee Chukka Boot (Men)

$159.95 – $170.00
(111)
Free Delivery
Product Image
Nordstrom

William Waterproof Side Zip Boot (Men)

Now:$57.97 – $64.97
Was:$129.95Up to 55% off select colors/sizes
(5)
Free Delivery
Product Image
UGG®

Neumel Chukka Boot (Men)

$130.00 – $140.00
(3615)
Free Delivery
Product Image
Clarks®

Desert Chukka Boot (Men)

$149.95 – $150.00
(159)
Free Delivery
Product Image
New Markdown
Blondo

Noah Waterproof Lace-Up Boot (Men)

Now:$80.97
Was:$180.0055% off
(1)
Free Delivery
Product Image
Blundstone Footwear

Blundstone Water Resistant Chelsea Boot (Men)

$204.95
(1)
Free Delivery
Product Image
UGG®

Neumel Chelsea Boot (Men)

$130.00
(40)
Free Delivery
Product Image
Bogs

Classic High Waterproof Boot (Men)

$130.00
(162)
Free Delivery
Product Image
Timberland

6 Inch Premium Waterproof Boot (Men)

$198.00
(3184)
Free Delivery
Product Image
Timberland

6 Inch Premium Waterproof Boot (Men)

Now:$99.00 – $198.00
Was:$198.00Up to 50% off select colors/sizes
(2678)
Free Delivery
Product Image
New Markdown
Blondo

Konor Waterproof Chukka Boot (Men)

Now:$69.97 – $150.00
Was:$150.00Up to 53% off select colors/sizes
(10)
Free Delivery
Product Image
Cole Haan

Warner Waterproof Chelsea Boot (Men)

$220.00
Free Delivery
Product Image
Blundstone Footwear

Blundstone Classic 550 Series Water Resistant Chelsea Boot (Men)

$209.95
(3)
Free Delivery
Product Image
Clarks®

Wallabee Chukka Boot (Men)

$199.95
Free Delivery
Product Image
UGG®

UGG Emmett Waterproof Snow Boot (Men)

$130.00
(130)
Free Delivery
Product Image
Ariat

Midtown Rambler Mid Chelsea Boot (Men)

$149.95
(60)
Free Delivery
Product Image
UGG®

Butte Waterproof Boot (Men)

$224.95
(882)
Free Delivery
Product Image
ECCO

Track 25 Boot (Men)

$249.95
(8)
Free Delivery
Product Image
Clarks®

Originals 'Desert' Boot (Men)

$130.00
(134)
Free Delivery
Product Image
Cole Haan

Warner GrandPro Waterproof Chukka Boot (Men)

Now:$134.00
Was:$200.0033% off
(1)
Free Delivery
Product Image
Bogs

Digger Waterproof Slip-On (Men)

$70.00
Free Delivery
Product Image
Bogs

Digger Waterproof Boot (Men)

$80.00
Free Delivery
Product Image
Timberland

6-Inch Premium Waterproof Boot (Men)

$198.00
(2733)
Free Delivery
Product Image
Josef Seibel

'Oscar 11' Chukka Boot (Men)

$185.00
(3)
Free Delivery
Product Image
Sperry

x John Legend Commodore Boot (Men)

Now:$89.97
Was:$200.0055% off
(2)
Free Delivery
Product Image
Teva

Ember Commute Waterproof Boot (Men)

Now:$103.97 – $140.00
Was:$140.00Up to 25% off select colors/sizes
(21)
Free Delivery
Product Image
ECCO

CityTray Avant Boot (Men)

$199.95
(2)
Free Delivery
Product Image
Timberland

Mt. Maddsen LTE Waterproof Hiking Boot (Men)

Now:$80.50
Was:$115.0030% off
(43)
Free Delivery
Product Image
Cole Haan

Original Grand Chukka Boot (Men)

$180.00
(10)
Free Delivery
Product Image
Blondo

Grant Waterproof Chelsea Boot (Men)

Now:$112.50
Was:$150.0025% off
(11)
Free Delivery
Product Image
Fly London

Moze Chelsea Boot (Men)

$300.00
Free Delivery
Product Image
New Markdown
Cole Haan

ZerøGrand Waterproof Chelsea Boot (Men)

Now:$112.97
Was:$250.0054% off
Free Delivery
Product Image
Bogs

Bozeman Tall Waterproof Boot (Men)

$150.00
(117)
Free Delivery
Product Image
ECCO

Soft 7 Tred Water Repellent Bootie (Men)

$179.95
Free Delivery
Product Image
Minnetonka

Fringe Boot (Men)

$59.95
(6)
Free Delivery
Product Image
ECCO

Hyrid Gore-Tex® Waterproof Chukka Boot (Men)

$229.95
(2)
Free Delivery
Product Image
Timberland

Port Union Chelsea Boot (Men)

$145.00
Free Delivery
Product Image
Teva

Riva Waterproof Mid Boot (Men)

$160.00
(1)
Free Delivery
Product Image
Bogs

Bog Classic Casual Waterproof Hiker Boot (Men)

$140.00
Free Delivery
Product Image
Bogs

Classic Casual Waterproof Chukka (Men)

$135.00
Free Delivery
Product Image
Blundstone Footwear

Blundstone Super 550 Series Chelsea Boot (Men)

$219.95
Free Delivery
Product Image
Teva

ReEmber Mid Water Repellent Bootie (Men)

$90.00
(10)
Free Delivery
Product Image
Blundstone Footwear

Chelsea Boot (Unisex)

$209.95
(16)
Free Delivery
Product Image
New Markdown
Cole Haan

ZerøGrand Omni Chelsea Boot (Men)

Now:$143.97 – $320.00
Was:$320.00Up to 55% off select colors/sizes
Free Delivery
Product Image
L.L.Bean

6-Inch Waterproof Bean Boot (Men)

$129.00
(916)
Free Delivery
Product Image
UGG®

Gatson Waterproof Boot (Men)

$120.00
(3)
Free Delivery
Product Image
Blondo

Konor Waterproof Chukka Boot (Men)

$150.00
(10)
Free Delivery
Product Image
Camper

lab Eki Leather Boot (Men)

$575.00
Free Delivery
Product Image
Clarks®

Desert 2 Chukka Boot (Men)

$140.00
(7)
Free Delivery
Product Image
Børn

Nash Chukka Boot (Men)

$110.00
Free Delivery
Product Image
Cole Haan

ZerøGrand Waterproof Boot (Men)

Now:$127.97 – $143.97
Was:$320.00Up to 60% off select colors/sizes
(5)
Free Delivery
Product Image
Bogs

Sauvie Waterproof Chelsea Boot (Men)

$95.00
(171)
Free Delivery
Product Image
Chaco

Fields Waterproof Chelsea Boot (Men)

$150.00
Free Delivery
Product Image
Blundstone Footwear

Blundstone Original 500 Water Resistant Chelsea Boot (Men)

$199.95
Free Delivery
Product Image
L.L.Bean

Mountain Classic Waterproof Hiking Boot (Men)

$139.00
(15)
Free Delivery
Product Image
Merrell

x Adsum Moab 2 Gore-Tex® Mid Hiking Boot (Men)

$160.00
(2)
Free Delivery
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Clarks®

Courtlite Desert Boot (Men)

$130.00
Free Delivery
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Ariat

Circuit Patriot Square Toe Cowboy Boot (Men)

$199.95
(10)
Free Delivery
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Bogs

Bozeman Mid Waterproof Boot (Men)

$145.00
(81)
Free Delivery
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UGG®

Stenton Water Repellent Leather Boot (Men)

$190.00
(5)
Free Delivery
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Mephisto

Pitt Mid Lace-Up Boot (Men)

$449.00
(1)
Free Delivery
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Blondo

Kingston Waterproof Moc Toe Boot (Men)

$170.00
Free Delivery
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OluKai

Nalukai Boot (Men)

$140.00
(30)
Free Delivery
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Børn

Sean Plain Toe Boot (Men)

$170.00
Free Delivery
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Sperry

Gold Commodore PLUSHWAVE Chukka Boot (Men)

$190.00
(2)
Free Delivery
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Spring Step

Abram Leather Boot (Men)

$119.95
Free Delivery
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Twisted X

Original Driving Moc Chukka Boot (Men)

$124.95
(1)
Free Delivery
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Ariat

Plano Cowboy Boot (Men)

$219.95
(6)
Free Delivery
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New Markdown
Cole Haan

Original Grand Chukka Boot (Men)

Now:$113.97
Was:$190.0040% off
(6)
Free Delivery
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Florsheim

'Midtown' Zip Boot (Men)

$130.00
(54)
Free Delivery
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Blondo

Dean Waterproof Plain Toe Boot (Men)

$160.00
(1)
Free Delivery
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UGG®

Neumel Weather II Waterproof Boot (Men)

$150.00
(1)
Free Delivery
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