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Men's Boots Under $100

  • All Boots
  • Chelsea
  • Chukka
  • Combat & Lace-Up
  • Comfort
  • Dress Boots
  • Boots Under $100
242 items
2976 Lo Rogue Chelsea Boot (Men)
Dr. Martens

2976 Lo Rogue Chelsea Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
Convoy Fleece Boot (Men)
LUGZ

Convoy Fleece Boot (Men)

$49.97Current Price $49.97
(41% off)41% off.
$85.00Comparable value $85.00
(2)
Stratton Chukka Boot (Men)
VANCE CO

Stratton Chukka Boot (Men)

$74.97Current Price $74.97
(31% off)31% off.
$109.99Comparable value $109.99
(1)
Madson II Moc Toe Waterproof Boot (Men)
SOREL

Madson II Moc Toe Waterproof Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(35)
Peter Boot (Men)
Steve Madden

Peter Boot (Men)

$44.98Current Price $44.98
(73% off)73% off.
$170.00Comparable value $170.00
(4)
Esmond Plain Toe Chukka Boot (Men)
Dockers®

Esmond Plain Toe Chukka Boot (Men)

$59.97Current Price $59.97
(29% off)29% off.
$85.00Comparable value $85.00
(10)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Storm Chelsea Rain Boot (Men)
Barbour

Storm Chelsea Rain Boot (Men)

$69.97Current Price $69.97
(30% off)30% off.
$100.00Comparable value $100.00
(2)
Landon Chelsea Boot - Wide Width (Men)
VANCE CO

Landon Chelsea Boot - Wide Width (Men)

$44.97 – $49.97Current Price $44.97 to $49.97
(Up to 47% off)Up to 47% off.
$84.99Comparable value $84.99
(10)
Tempest Chukka Boot (Men)
New
Peter Millar

Tempest Chukka Boot (Men)

$99.97Current Price $99.97
(66% off)66% off.
$295.00Comparable value $295.00
(3)
Only a few left
Kingham Waterproof Boot (Men)
Ariat

Kingham Waterproof Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$184.95Comparable value $184.95
(22)
Questo Brogue Combat Boot (Men)
La Milano

Questo Brogue Combat Boot (Men)

$79.97Current Price $79.97
(1)
Excavate Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

Excavate Plain Toe Boot - Wide Width Available (Men)

$64.97Current Price $64.97
(Up to 31% off)Up to 31% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(4)
Circuit Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Circuit Plain Toe Chukka Boot - Wide Width Available (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(17)
Vesto Chukka Boot (Men)
Kenneth Cole Reaction

Vesto Chukka Boot (Men)

$69.97Current Price $69.97
(41% off)41% off.
$119.00Comparable value $119.00
(1)
Speed Solo Waterproof Mid Hiking Sneaker (Men)
Merrell

Speed Solo Waterproof Mid Hiking Sneaker (Men)

$94.97Current Price $94.97
(40% off)40% off.
$160.00Comparable value $160.00
(5)
Bowery Lug Sole Boot (Men)
GREATS

Bowery Lug Sole Boot (Men)

$49.97Current Price $49.97
(74% off)74% off.
$199.00Comparable value $199.00
Only a few left
Parker Wingtip Boot (Men)
VINTAGE FOUNDRY

Parker Wingtip Boot (Men)

$59.97Current Price $59.97
(59% off)59% off.
$149.00Comparable value $149.00
(4)
Whitby Chukka Boot (Men)
Ben Sherman

Whitby Chukka Boot (Men)

$49.97Current Price $49.97
(47% off)47% off.
$95.00Comparable value $95.00
(4)
Only a few left
Hills Chelsea Boot (Men)
Anthony Veer

Hills Chelsea Boot (Men)

$74.97 – $79.97Current Price $74.97 to $79.97
(Up to 48% off)Up to 48% off.
$145.95 – $145.99Comparable value $145.95 to $145.99
Moab 3 Mid Waterproof Hiking Shoe (Men)
Merrell

Moab 3 Mid Waterproof Hiking Shoe (Men)

$99.97Current Price $99.97
(41% off)41% off.
$170.00Comparable value $170.00
(414)
Only a few left
Emmett Waterproof Snow Boot (Men)
UGG®

Emmett Waterproof Snow Boot (Men)

$99.97Current Price $99.97
(33% off)33% off.
$150.00Comparable value $150.00
(136)
Only a few left
Wallabee Chukka Boot (Men)
Clarks® Originals

Wallabee Chukka Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
Spitfire Leather Chukka Boot (Men)
Ariat

Spitfire Leather Chukka Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.95Comparable value $129.95
(341)
Only a few left
Native Johnny Treklite Water Repellent Boot (Men)
Native Shoes

Native Johnny Treklite Water Repellent Boot (Men)

$74.97Current Price $74.97
(31% off)31% off.
$110.00Comparable value $110.00
Anderson Casual Chukka Boot (Men)
VINTAGE FOUNDRY

Anderson Casual Chukka Boot (Men)

$69.97Current Price $69.97
(60% off)60% off.
$175.00Comparable value $175.00
Koen Chukka Boot (Men)
Mykos

Koen Chukka Boot (Men)

$74.97Current Price $74.97
(21% off)21% off.
$94.99Comparable value $94.99
Wallabee Chukka (Men)
Clarks®

Wallabee Chukka (Men)

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
Delton Plain Toe Chukka Boot (Men)
NUNN BUSH

Delton Plain Toe Chukka Boot (Men)

$54.97Current Price $54.97
(42% off)42% off.
$95.00Comparable value $95.00
Slabtown 62 Waterproof Moc Toe Boot (Men)
SOREL

Slabtown 62 Waterproof Moc Toe Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$180.00Comparable value $180.00
Only a few left
Walton Lace-Up Boot (Men)
New
ALDO

Walton Lace-Up Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
Banks Moc Toe Chukka Boot (Men)
Thomas & Vine

Banks Moc Toe Chukka Boot (Men)

$54.97Current Price $54.97
(71% off)71% off.
$189.99Comparable value $189.99
(1)
Only a few left
Chamonix Vegan Water Resistant Boot (Men)
Native Shoes

Chamonix Vegan Water Resistant Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(1)
Zuma II Boot (Men)
Dr. Martens

Zuma II Boot (Men)

$74.97Current Price $74.97
(42% off)42% off.
$130.00Comparable value $130.00
(15)
Combs Coated Boot (Men)
New
Dr. Martens

Combs Coated Boot (Men)

$89.97Current Price $89.97
(35% off)35% off.
$140.00Comparable value $140.00
Only a few left
Spitfire Leather Chukka Boot (Men)
Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$139.95Comparable value $139.95
(57)
Lite Hybrid Chukka Boot (Men)
ECCO

Lite Hybrid Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
(1)
Otto Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$49.97 – $79.97Current Price $49.97 to $79.97
(Up to 58% off)Up to 58% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
(14)
Grand Remix Chukka Boot (Men)
Cole Haan

Grand Remix Chukka Boot (Men)

$99.97Current Price $99.97
(54% off)54% off.
$220.00Comparable value $220.00
(15)
Only a few left
Karnak Water Resistant Plain Toe Boot - Wide Width Available (Men)
NUNN BUSH

Karnak Water Resistant Plain Toe Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
Joel Boot (Men)
XRAY

Joel Boot (Men)

$39.97Current Price $39.97
(50% off)50% off.
$80.00Comparable value $80.00
(3)
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Marion Faux Leather Boot (Men)
XRAY

Marion Faux Leather Boot (Men)

$39.97Current Price $39.97
(50% off)50% off.
$80.00Comparable value $80.00
Groundbreaker Western Work Boot (Men)
Ariat

Groundbreaker Western Work Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
Shepton Easy Chelsea Boot (Men)
Clarks®

Shepton Easy Chelsea Boot (Men)

$94.97Current Price $94.97
(26% off)26% off.
$130.00Comparable value $130.00
Only a few left
Zeus Lace-Up Boot (Men)
VANCE CO

Zeus Lace-Up Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$109.99Comparable value $109.99
Faux Shearling Lined Winter Boot (Men)
AVALANCHE

Faux Shearling Lined Winter Boot (Men)

$29.97Current Price $29.97
(40% off)40% off.
$49.99Comparable value $49.99
(3)
Connor Suede Chelsea Boot (Men)
Frye

Connor Suede Chelsea Boot (Men)

$99.97Current Price $99.97
(49% off)49% off.
$198.00Comparable value $198.00
(1)
Only a few left
Slater Chelsea Boot (Men)
VANCE CO

Slater Chelsea Boot (Men)

$74.97Current Price $74.97
(31% off)31% off.
$109.99Comparable value $109.99
(1)
Bassel Boot (Men)
VINTAGE FOUNDRY

Bassel Boot (Men)

$79.97Current Price $79.97
(70% off)70% off.
$269.00Comparable value $269.00
Authentic Original Double Sole Chukka (Men)
New
Sperry

Authentic Original Double Sole Chukka (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
Gibson Waterproof Winter Boot (Men)
ALDO

Gibson Waterproof Winter Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(1)
Only a few left
Stone Faux Fur Trim Leather Boot
VINTAGE FOUNDRY

Stone Faux Fur Trim Leather Boot

$39.97Current Price $39.97
(69% off)69% off.
$129.00Comparable value $129.00
(4)
Eddy Waterproof Leather Boot (Men)
Align

Eddy Waterproof Leather Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
(2)
Wallabee FTR2 Moc Toe Chukka Boot (Men)
Clarks®

Wallabee FTR2 Moc Toe Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Spitfire All Terrain Waterproof Chukka Boot (Men)
Ariat

Spitfire All Terrain Waterproof Chukka Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$169.95Comparable value $169.95
(12)
Denver Lug Sole Boot (Men)
VANCE CO

Denver Lug Sole Boot (Men)

$59.97Current Price $59.97
(45% off)45% off.
$109.99Comparable value $109.99
(1)
Dustin Boot (Men)
Dockers®

Dustin Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
695 Lace-Up Boot (Men)
Under Armour

695 Lace-Up Boot (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
(7)
Prescot Mid Top Sneaker (Men)
Lee

Prescot Mid Top Sneaker (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
Ozark II Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Ozark II Chukka Boot - Wide Width Available (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(3)
Farrell Lace-Up Boot (Men)
ALDO

Farrell Lace-Up Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(6)
Jefry Chukka Boot (Men)
New
ALDO

Jefry Chukka Boot (Men)

$89.97Current Price $89.97
(40% off)40% off.
$150.00Comparable value $150.00
Zion Chukka Boot (Men)
RESERVE FOOTWEAR

Zion Chukka Boot (Men)

$39.97Current Price $39.97
(50% off)50% off.
$80.00Comparable value $80.00
(3)
Excavate Water Resistant Moc Toe Boot (Men)
NUNN BUSH

Excavate Water Resistant Moc Toe Boot (Men)

$69.97Current Price $69.97
(26% off)26% off.
$95.00Comparable value $95.00
(4)
Graveldiver Waterproof Boot (Men)
ALDO

Graveldiver Waterproof Boot (Men)

$79.97Current Price $79.97
(51% off)51% off.
$165.00Comparable value $165.00
Only a few left
Gender Inclusive Zebzag 4-Eye Lace-Up Boot
Dr. Martens

Gender Inclusive Zebzag 4-Eye Lace-Up Boot

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
(1)
Arno Waterproof Snow Boot (Men)
POLAR RANGE

Arno Waterproof Snow Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(2)
Only a few left
Camden Chelsea Boot (Men)
Dockers®

Camden Chelsea Boot (Men)

$59.99Current Price $59.99
(29% off)29% off.
$85.00Comparable value $85.00
Yukon Waterproof Snow Boot (Men)
POLAR RANGE

Yukon Waterproof Snow Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(2)
Only a few left
Tobias Lug Sole Boot (Men)
Dockers®

Tobias Lug Sole Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(6)
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