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Men's Boots Under $100

  • All Boots
  • Chelsea
  • Chukka
  • Combat & Lace-Up
  • Comfort
  • Dress Boots
  • Boots Under $100
228 items
Terrex Anylander Mid R.RDY Waterproof Hiking Boot (Men)
New
adidas

Terrex Anylander Mid R.RDY Waterproof Hiking Boot (Men)

$79.97Current Price $79.97
(20% off)20% off.
$100.00Comparable value $100.00
(624)
Gender Inclusive 1460 Pascal Desert Brown Boot
Dr. Martens

Gender Inclusive 1460 Pascal Desert Brown Boot

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
(5)
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$49.98Current Price $49.98
(71% off)71% off.
$175.00Comparable value $175.00
(17)
Gender Inclusive Rilla Utility Boot
Dr. Martens

Gender Inclusive Rilla Utility Boot

$74.97Current Price $74.97
(42% off)42% off.
$130.00Comparable value $130.00
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$69.96Current Price $69.96
(51% off)51% off.
$145.00Comparable value $145.00
(122)
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)
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)
Gender Inclusive 101 Lace-Up Boot
Dr. Martens

Gender Inclusive 101 Lace-Up Boot

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(3)
Shepton Chukka Boot (Men)
Clarks®

Shepton Chukka Boot (Men)

$74.97Current Price $74.97
(Up to 31% off)Up to 31% off.
$100.00 – $110.00Comparable value $100.00 to $110.00
(5)
Chalet Leather Cap Toe Boot (Men)
Florsheim

Chalet Leather Cap Toe Boot (Men)

$59.98Current Price $59.98
(61% off)61% off.
$155.00Comparable value $155.00
(23)
Derrk Chelsea Boot (Men)
BOSS

Derrk Chelsea Boot (Men)

$79.96Current Price $79.96
(73% off)73% off.
$299.00Previous Price $299.00
New Markdown
(1)
Only a few left
Gerard Lug Sole Boot (Men)
RESERVE FOOTWEAR

Gerard Lug Sole Boot (Men)

$34.97Current Price $34.97
(72% off)72% off.
$125.00Comparable value $125.00
(6)
Wexford Chelsea Boot (Men)
Ariat

Wexford Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(4)
Sesame Chelsea Boot (Men)
Tommy Hilfiger

Sesame Chelsea Boot (Men)

$54.97Current Price $54.97
(53% off)53% off.
$119.00Comparable value $119.00
(41)
Tempo Sol Waterproof Hiking Boot (Men)
Merrell

Tempo Sol Waterproof Hiking Boot (Men)

$59.97Current Price $59.97
(25% off)25% off.
$80.00Comparable value $80.00
(1)
Taskorn Combat Boot (Men)
MADDEN

Taskorn Combat Boot (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(50)
New Tunley Chelsea Boot (Men)
BOSS

New Tunley Chelsea Boot (Men)

$58.48 – $149.97Current Price $58.48 to $149.97
(Up to 70% off select items)Up to 70% off select items.
$199.00Comparable value $199.00
(4)
Zuma II Boot (Men)
Dr. Martens

Zuma II Boot (Men)

$74.97Current Price $74.97
(42% off)42% off.
$130.00Comparable value $130.00
(14)
Tristen Boot (Men)
MADDEN

Tristen Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(51)
Lafayette Chukka Boot (Men)
Vince

Lafayette Chukka Boot (Men)

$89.99 – $109.99Current Price $89.99 to $109.99
(Up to 74% off)Up to 74% off.
$350.00Comparable value $350.00
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
'Lookout' Moc Toe Boot (Men)
Ariat

'Lookout' Moc Toe Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$159.95Comparable value $159.95
(71)
Peter Boot (Men)
Steve Madden

Peter Boot (Men)

$44.98Current Price $44.98
(73% off)73% off.
$170.00Comparable value $170.00
(4)
Volland Boot (Men)
Call It Spring By Aldo

Volland Boot (Men)

$49.97Current Price $49.97
(47% off)47% off.
$94.99Comparable value $94.99
Sawyer Chelsea Boot (Men)
MADDEN

Sawyer Chelsea Boot (Men)

$24.98 – $34.96Current Price $24.98 to $34.96
(Up to 72% off)Up to 72% off.
$90.00Comparable value $90.00
(15)
Lockhart Mini Lug Suede Chelsea Boot (Men)
Nordstrom

Lockhart Mini Lug Suede Chelsea Boot (Men)

$49.97Current Price $49.97
(58% off)58% off.
$119.95Comparable value $119.95
(2)
Whitman Chukka Boot (Men)
VITTORIO RUSSO

Whitman Chukka Boot (Men)

$84.98 – $89.98Current Price $84.98 to $89.98
(Up to 62% off)Up to 62% off.
$225.00Comparable value $225.00
(3)
Attleboro Mid Chukka Boot (Men)
Timberland

Attleboro Mid Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
(5)
Bushwick Chukka Boot (Men)
Anthony Veer

Bushwick Chukka Boot (Men)

$74.97Current Price $74.97
(48% off)48% off.
$145.99Comparable value $145.99
(1)
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
Cian Side Zip Boot (Men)
Dune London

Cian Side Zip Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
Shepton Easy Chelsea Boot (Men)
Clarks®

Shepton Easy Chelsea Boot (Men)

$64.98 – $94.97Current Price $64.98 to $94.97
(Up to 50% off select items)Up to 50% off select items.
$130.00Comparable value $130.00
Martin Chelsea Boot (Men)
VINTAGE FOUNDRY

Martin Chelsea Boot (Men)

$49.97Current Price $49.97
(71% off)71% off.
$175.00Comparable value $175.00
(9)
Circuit Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$24.73 – $54.97Current Price $24.73 to $54.97
(Up to 72% off select items)Up to 72% off select items.
$90.00Comparable value $90.00
(17)
Jasper Zip-Up Boot (Men)
New
Steve Madden

Jasper Zip-Up Boot (Men)

$99.97Current Price $99.97
(42% off)42% off.
$175.00Comparable value $175.00
Only a few left
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
Marlow Chukka Boot (Men)
VINTAGE FOUNDRY

Marlow Chukka Boot (Men)

$54.97Current Price $54.97
(70% off)70% off.
$185.00Comparable value $185.00
(1)
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Donovan Side Zip Boot (Men)
Call It Spring By Aldo

Donovan Side Zip Boot (Men)

$39.97Current Price $39.97
(50% off)50% off.
$79.99Comparable value $79.99
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
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)
Zeus Lace-Up Boot (Men)
New
VANCE CO

Zeus Lace-Up Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$109.99Comparable value $109.99
Newmark Grand Water Resistant Chelsea Boot (Men)
Cole Haan

Newmark Grand Water Resistant Chelsea Boot (Men)

$97.47Current Price $97.47
(72% off)72% off.
$360.00Comparable value $360.00
(10)
Only a few left
Gainsly Chelsea Boot (Men)
Tommy Hilfiger

Gainsly Chelsea Boot (Men)

$41.96 – $59.97Current Price $41.96 to $59.97
(Up to 66% off select items)Up to 66% off select items.
$125.00Comparable value $125.00
(2)
Joel Boot (Men)
XRAY

Joel Boot (Men)

$39.97Current Price $39.97
(50% off)50% off.
$80.00Comparable value $80.00
(3)
Vesto Chukka Boot (Men)
New
Kenneth Cole Reaction

Vesto Chukka Boot (Men)

$69.97Current Price $69.97
(41% off)41% off.
$119.00Comparable value $119.00
(1)
Colby Chelsea Boot (Men)
BOSS

Colby Chelsea Boot (Men)

$99.99 – $149.97Current Price $99.99 to $149.97
(Up to 49% off select items)Up to 49% off select items.
$199.00Comparable value $199.00
(2)
Slabtown '62™ Waterproof Moc Toe Boot (Men)
SOREL

Slabtown '62™ Waterproof Moc Toe Boot (Men)

$99.97Current Price $99.97
(42% off)42% off.
$175.00Comparable value $175.00
(11)
Speed Strike 2 Waterproof Hiking Boot (Men)
New
Merrell

Speed Strike 2 Waterproof Hiking Boot (Men)

$84.97 – $89.97Current Price $84.97 to $89.97
(Up to 25% off)Up to 25% off.
$110.00 – $120.00Comparable value $110.00 to $120.00
(17)
P-Ely Wingtip Boot (Men)
Steve Madden

P-Ely Wingtip Boot (Men)

$59.98Current Price $59.98
(64% off)64% off.
$170.00Comparable value $170.00
Dann Lugged Chukka Boot (Men)
Vince

Dann Lugged Chukka Boot (Men)

$99.99Current Price $99.99
(73% off)73% off.
$375.00Comparable value $375.00
(3)
Only a few left
'Lumber Up' Moc Toe Boot (Men)
Eastland

'Lumber Up' Moc Toe Boot (Men)

$74.96 – $99.97Current Price $74.96 to $99.97
(Up to 50% off select items)Up to 50% off select items.
$135.00 – $150.00Comparable value $135.00 to $150.00
(5)
Joplin Lace Up Boot (Men)
Donald Pliner

Joplin Lace Up Boot (Men)

$89.98 – $149.97Current Price $89.98 to $149.97
(Up to 72% off select items)Up to 72% off select items.
$325.00Comparable value $325.00
(3)
Kingham Waterproof Boot (Men)
Ariat

Kingham Waterproof Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$184.95Comparable value $184.95
(22)
Madson II Moc Toe Waterproof Boot (Men)
New
SOREL

Madson II Moc Toe Waterproof Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(35)
Weltridge Side Zip Boot (Men)
Clarks®

Weltridge Side Zip Boot (Men)

$94.97Current Price $94.97
(26% off)26% off.
$130.00Comparable value $130.00
(3)
Josiah Chelsea Boot (Men)
New
VANCE CO

Josiah Chelsea Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$109.99Comparable value $109.99
Bodie Cowboy Boot (Men)
Ariat

Bodie Cowboy Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
(18)
Wallaston Low Chukka Boot (Men)
Clarks®

Wallaston Low Chukka Boot (Men)

$84.97Current Price $84.97
(22% off)22% off.
$110.00Comparable value $110.00
(2)
Jaxen Easy Chelsea Boot (Men)
Clarks®

Jaxen Easy Chelsea Boot (Men)

$99.97Current Price $99.97
(16% off)16% off.
$120.00Comparable value $120.00
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)
Across II Cap Toe Chukka Boot (Men)
La Milano

Across II Cap Toe Chukka Boot (Men)

$79.97Current Price $79.97
(20% off)20% off.
$99.99Comparable value $99.99
Darnell Zip Boot (Men)
VANCE CO

Darnell Zip Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$109.99Comparable value $109.99
(2)
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
Rowan Lug Sole Boot (Men)
Lee

Rowan Lug Sole Boot (Men)

$74.97Current Price $74.97
(25% off)25% off.
$100.00Comparable value $100.00
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)
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
Neumel Chukka Boot (Men)
UGG®

Neumel Chukka Boot (Men)

$99.97Current Price $99.97
(33% off)33% off.
$150.00Comparable value $150.00
(461)
Only a few left
Jaxon II Cap Toe Boot (Men)
La Milano

Jaxon II Cap Toe Boot (Men)

$79.97Current Price $79.97
(20% off)20% off.
$99.99Comparable value $99.99
(1)
Only a few left
Karnak Water Resistant Moc Toe Boot (Men)
NUNN BUSH

Karnak Water Resistant Moc Toe Boot (Men)

$17.99 – $89.97Current Price $17.99 to $89.97
(Up to 85% off select items)Up to 85% off select items.
$110.00 – $120.00Comparable value $110.00 to $120.00
(3)
Torhill Lo Chukka Boot (Men)
Clarks®

Torhill Lo Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$130.00Comparable value $130.00
George Chukka Boot (Men)
Anthony Veer

George Chukka Boot (Men)

$99.97Current Price $99.97
(39% off)39% off.
$165.95Comparable value $165.95
(1)
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