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Men's Boots Under $100

  • All Boots
  • Chelsea
  • Chukka
  • Combat & Lace-Up
  • Comfort
  • Dress Boots
  • Rain & Snow
  • Boots Under $100
251 items
Newmark Grand Chelsea Boot (Men)
Cole Haan

Newmark Grand Chelsea Boot (Men)

$58.48Current Price $58.48
(Extra 40% off)Includes extra 40% off.
$97.47Previous Price $97.47
$360.00Comparable value $360.00
Price Drop
(1)
Lite Hybrid Chukka Boot (Men)
New
ECCO

Lite Hybrid Chukka Boot (Men)

$79.97Current Price $79.97
(42% off)42% off.
$140.00Comparable value $140.00
Dain Combat Boot (Men)
Allen Edmonds

Dain Combat Boot (Men)

$80.97 – $179.97Current Price $80.97 to $179.97
(Extra 40% off select items)Includes extra 40% off select items.
$134.96Previous Price $134.96
$495.00Comparable value $495.00
Price Drop
(18)
Slabtown 62 Waterproof Moc Toe Boot (Men)
New
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
Hi-Line Waterproof Lace-Up Boot (Men)
SOREL

Hi-Line Waterproof Lace-Up Boot (Men)

$62.96Current Price $62.96
(65% off)65% off.
$185.00Comparable value $185.00
(27)
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$40.48 – $89.97Current Price $40.48 to $89.97
(Extra 40% off select items)Includes extra 40% off select items.
$67.47Previous Price $67.47
$175.00Comparable value $175.00
Price Drop
(12)
Chamberlin Grand Chukka Boot (Men)
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$58.48 – $129.97Current Price $58.48 to $129.97
(Extra 40% off select items)Includes extra 40% off select items.
$97.47Previous Price $97.47
$290.00Comparable value $290.00
Price Drop
(5)
Morse GRANDFØAM Chukka Boot (Men)
Cole Haan

Morse GRANDFØAM Chukka Boot (Men)

$50.68 – $129.97Current Price $50.68 to $129.97
(Extra 40% off select items)Includes extra 40% off select items.
$84.48 – $97.47Previous Price $84.48 to $97.47
$220.00Comparable value $220.00
Price Drop
(1)
Nalukai Kala Moc Toe Boot (Men)
OluKai

Nalukai Kala Moc Toe Boot (Men)

$49.99Current Price $49.99
(64% off)64% off.
$140.00Comparable value $140.00
(1)
Only a few left
Theo Chukka Boot (Men)
Børn

Theo Chukka Boot (Men)

$33.57 – $35.97Current Price $33.57 to $35.97
(Extra 40% off)Includes extra 40% off.
$55.96 – $59.96Previous Price $55.96 to $59.96
$130.00Comparable value $130.00
Price Drop
(9)
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)
Only a few left
Grand Atlantic Chelsea Boot (Men)
Cole Haan

Grand Atlantic Chelsea Boot (Men)

$44.97Current Price $44.97
(Extra 40% off)Includes extra 40% off.
$74.96Previous Price $74.96
$200.00Comparable value $200.00
Price Drop
(4)
Slabtown '62™ Waterproof Moc Toe Boot (Men)
New
SOREL

Slabtown '62™ Waterproof Moc Toe Boot (Men)

$99.97Current Price $99.97
(42% off)42% off.
$175.00Comparable value $175.00
(11)
Ryan Lug Sole Boot (Men)
BOSS

Ryan Lug Sole Boot (Men)

$99.97Current Price $99.97
(56% off)56% off.
$230.00Comparable value $230.00
Gender Inclusive 1460 Pascal Desert Brown Boot
New
Dr. Martens

Gender Inclusive 1460 Pascal Desert Brown Boot

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
Wallaston Chukka Boot (Men)
Clarks®

Wallaston Chukka Boot (Men)

$35.97 – $79.97Current Price $35.97 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$59.96Previous Price $59.96
$120.00Comparable value $120.00
Price Drop
(2)
Peter Chelsea Boot (Men)
VITTORIO RUSSO

Peter Chelsea Boot (Men)

$50.68 – $58.48Current Price $50.68 to $58.48
(Extra 40% off)Includes extra 40% off.
$84.48 – $97.47Previous Price $84.48 to $97.47
$225.00Comparable value $225.00
Price Drop
(6)
Cyprus™ Waterproof Chelsea Boot (Men)
New
SOREL

Cyprus™ Waterproof Chelsea Boot (Men)

$74.99Current Price $74.99
(40% off)40% off.
$125.00Previous Price $125.00
Only a few left
2976 Wintergrip Water Resistant Chelsea Boot (Men)
Dr. Martens

2976 Wintergrip Water Resistant Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$190.00Comparable value $190.00
(54)
Only a few left
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
(4)
Wexford Chelsea Boot (Men)
New
Ariat

Wexford Chelsea Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(4)
June Chukka Boot (Men)
Vince

June Chukka Boot (Men)

$58.48 – $67.48Current Price $58.48 to $67.48
(Extra 40% off)Includes extra 40% off.
$97.48 – $112.47Previous Price $97.48 to $112.47
$375.00Comparable value $375.00
Price Drop
(1)
'Lumber Up' Moc Toe Boot (Men)
Eastland

'Lumber Up' Moc Toe Boot (Men)

$35.97 – $99.97Current Price $35.97 to $99.97
(Extra 40% off select items)Includes extra 40% off select items.
$59.96 – $89.96Previous Price $59.96 to $89.96
$135.00 – $150.00Comparable value $135.00 to $150.00
Price Drop
(4)
Rosemead Chukka Boot (Men)
TO BOOT NEW YORK

Rosemead Chukka Boot (Men)

$74.08 – $85.48Current Price $74.08 to $85.48
(Extra 40% off)Includes extra 40% off.
$123.48 – $142.47Previous Price $123.48 to $142.47
$399.00Comparable value $399.00
Price Drop
Chamberlain Cap Toe Boot (Men)
Cole Haan

Chamberlain Cap Toe Boot (Men)

$58.48Current Price $58.48
(Extra 40% off)Includes extra 40% off.
$97.47Previous Price $97.47
$310.00Comparable value $310.00
Price Drop
(1)
Only a few left
Mac Hill™ Lite Waterproof Mid Plus Boot (Men)
SOREL

Mac Hill™ Lite Waterproof Mid Plus Boot (Men)

$59.98Current Price $59.98
(65% off)65% off.
$175.00Comparable value $175.00
(2)
Only a few left
Emmett Waterproof Snow Boot (Men)
UGG®

Emmett Waterproof Snow Boot (Men)

$59.96Current Price $59.96
(60% off)60% off.
$150.00Comparable value $150.00
(129)
Only a few left
Lockhart Mini Lug Suede Chelsea Boot (Men)
New
Nordstrom

Lockhart Mini Lug Suede Chelsea Boot (Men)

$49.97Current Price $49.97
(58% off)58% off.
$119.95Comparable value $119.95
(2)
Speed Strike 2 Hiking Boot (Men)
New
Merrell

Speed Strike 2 Hiking Boot (Men)

$89.97Current Price $89.97
(25% off)25% off.
$120.00Comparable value $120.00
(18)
Ankeny II Waterproof Hiking Boot (Men)
SOREL

Ankeny II Waterproof Hiking Boot (Men)

$89.97Current Price $89.97
(45% off)45% off.
$165.00Comparable value $165.00
(9)
Speed Solo Waterproof Mid Hiking Sneaker (Men)
New
Merrell

Speed Solo Waterproof Mid Hiking Sneaker (Men)

$94.97Current Price $94.97
(40% off)40% off.
$160.00Comparable value $160.00
(3)
Borland Chelsea Boot (Men)
Johnston & Murphy

Borland Chelsea Boot (Men)

$33.57 – $79.97Current Price $33.57 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$55.96Previous Price $55.96
$160.00Comparable value $160.00
Price Drop
(3)
Weltridge Side Zip Boot (Men)
Clarks®

Weltridge Side Zip Boot (Men)

$42.73 – $94.97Current Price $42.73 to $94.97
(Extra 40% off select items)Includes extra 40% off select items.
$71.22Previous Price $71.22
$130.00Comparable value $130.00
Price Drop
(2)
Attleboro Chelsea Boot (Men)
Timberland

Attleboro Chelsea Boot (Men)

$29.99Current Price $29.99
(Extra 40% off)Includes extra 40% off.
$49.99Previous Price $49.99
$130.00 – $140.00Comparable value $130.00 to $140.00
Price Drop
(8)
Norwich Chelsea Boot (Men)
Ted Baker London

Norwich Chelsea Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
Scotch Lug Sole Boot (Men)
Steve Madden

Scotch Lug Sole Boot (Men)

$79.97Current Price $79.97
(38% off)38% off.
$130.00Comparable value $130.00
(6)
Grand Atlantic Chukka Boot - Wide Width Available (Men)
Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (Men)

$44.97Current Price $44.97
(Extra 40% off)Includes extra 40% off.
$74.96Previous Price $74.96
$200.00Comparable value $200.00
Price Drop
(42)
Tucker Moc Toe Boot (Men)
rag & bone

Tucker Moc Toe Boot (Men)

$79.77Current Price $79.77
(Extra 40% off)Includes extra 40% off.
$132.96Previous Price $132.96
$478.00Comparable value $478.00
Price Drop
Only a few left
'Lookout' Moc Toe Boot (Men)
New
Ariat

'Lookout' Moc Toe Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$159.95Comparable value $159.95
(69)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(120)
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
Gender Inclusive 101 Lace-Up Boot
New
Dr. Martens

Gender Inclusive 101 Lace-Up Boot

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(2)
2.Zerogrand Chukka Boot (Men)
Cole Haan

2.Zerogrand Chukka Boot (Men)

$44.97 – $99.97Current Price $44.97 to $99.97
(Extra 40% off select items)Includes extra 40% off select items.
$74.96Previous Price $74.96
$338.00Comparable value $338.00
Price Drop
(403)
Claus Chukka Boot (Men)
Dune London

Claus Chukka Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
Skiff Chukka Boot (Men)
AllSaints

Skiff Chukka Boot (Men)

$73.48Current Price $73.48
(Extra 40% off)Includes extra 40% off.
$122.47Previous Price $122.47
$299.00Comparable value $299.00
Price Drop
(1)
Only a few left
Welch Chukka Boot (Men)
JOHNSTON & MURPHY COLLECTION

Welch Chukka Boot (Men)

$76.48Current Price $76.48
(Extra 40% off)Includes extra 40% off.
$127.47Previous Price $127.47
$265.00Comparable value $265.00
Price Drop
(9)
Gainsly Chelsea Boot (Men)
New
Tommy Hilfiger

Gainsly Chelsea Boot (Men)

$59.97Current Price $59.97
(52% off)52% off.
$125.00Comparable value $125.00
(1)
Kingham Waterproof Boot (Men)
New
Ariat

Kingham Waterproof Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$184.95Comparable value $184.95
(22)
Motion Ledge Mid Hiking Boot (Men)
Timberland

Motion Ledge Mid Hiking Boot (Men)

$69.97Current Price $69.97
(41% off)41% off.
$120.00Comparable value $120.00
Kenora Chukka Boot (Men)
ALDO

Kenora Chukka Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
(2)
Only a few left
Boulder Chukka Boot (Men)
Barbour

Boulder Chukka Boot (Men)

$50.37Current Price $50.37
(Extra 40% off)Includes extra 40% off.
$83.96Previous Price $83.96
$230.00Comparable value $230.00
Price Drop
(1)
Only a few left
Norwich Chelsea Boot (Men)
Ted Baker

Norwich Chelsea Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
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
(391)
Bonham Water Repellent Chelsea Boot (Men)
Vince

Bonham Water Repellent Chelsea Boot (Men)

$59.99Current Price $59.99
(Extra 40% off)Includes extra 40% off.
$99.99Previous Price $99.99
$350.00Comparable value $350.00
Price Drop
(1)
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
Eli Suede Chukka Boot (Men)
Børn

Eli Suede Chukka Boot (Men)

$35.08 – $40.48Current Price $35.08 to $40.48
(Extra 40% off)Includes extra 40% off.
$58.48 – $67.47Previous Price $58.48 to $67.47
$130.00Comparable value $130.00
Price Drop
(3)
Only a few left
Sutton Chukka Boot (Men)
GREATS

Sutton Chukka Boot (Men)

$59.97Current Price $59.97
(69% off)69% off.
$199.00Comparable value $199.00
(2)
Only a few left
Colby Chelsea Boot (Men)
BOSS

Colby Chelsea Boot (Men)

$58.48Current Price $58.48
(Extra 40% off)Includes extra 40% off.
$97.48Previous Price $97.48
$199.00Comparable value $199.00
Price Drop
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
Harbin Chukka Boot (Men)
Tommy Hilfiger

Harbin Chukka Boot (Men)

$23.38 – $59.97Current Price $23.38 to $59.97
(Extra 40% off select items)Includes extra 40% off select items.
$38.98Previous Price $38.98
$119.00Comparable value $119.00
Price Drop
(10)
Grand Lug Boot (Men)
New
Cole Haan

Grand Lug Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
Sport Stratten Leather Boot (Men)
New
Ariat

Sport Stratten Leather Boot (Men)

$99.97Current Price $99.97
(47% off)47% off.
$189.95Comparable value $189.95
(73)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Bronnie Combat Boot (Men)
MADDEN

Bronnie Combat Boot (Men)

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
(1)
Storm Chelsea Rain Boot (Men)
Barbour

Storm Chelsea Rain Boot (Men)

$69.97Current Price $69.97
(51% off)51% off.
$145.00Comparable value $145.00
(2)
Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)
UGG®

Neumal Crafted Regenerate Water Resistant Chukka Boot (Men)

$74.96Current Price $74.96
(62% off)62% off.
$200.00Comparable value $200.00
(4)
Only a few left
Thames Chukka Boot (Men)
Ben Sherman

Thames Chukka Boot (Men)

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
Azzano Plain Toe Chelsea Boot (Men)
Florsheim

Azzano Plain Toe Chelsea Boot (Men)

$49.48Current Price $49.48
(Extra 40% off)Includes extra 40% off.
$82.47Previous Price $82.47
$145.00Comparable value $145.00
Price Drop
Sawyer Chelsea Boot (Men)
Steve Madden

Sawyer Chelsea Boot (Men)

$20.97 – $49.97Current Price $20.97 to $49.97
(Extra 40% off select items)Includes extra 40% off select items.
$34.96Previous Price $34.96
$90.00Comparable value $90.00
Price Drop
(12)
Chicago Chukka Boot (Men)
New
Marc Joseph New York

Chicago Chukka Boot (Men)

$79.97Current Price $79.97
(58% off)58% off.
$195.00Comparable value $195.00
(1)
Avenue Duck Boot (Men)
Sperry

Avenue Duck Boot (Men)

$26.98Current Price $26.98
(Extra 40% off)Includes extra 40% off.
$44.97Previous Price $44.97
$120.00Comparable value $120.00
Price Drop
(19)
Madson II Chore Waterproof Boot (Men)
SOREL

Madson II Chore Waterproof Boot (Men)

$69.96Current Price $69.96
(64% off)64% off.
$195.00Comparable value $195.00
(12)
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