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  5. Boots Under $100

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Men's Boots Under $100

  • All Boots
  • Chelsea
  • Chukka
  • Combat & Lace-Up
  • Comfort
  • Dress Boots
  • Rain & Snow
  • Boots Under $100
262 items
Tristen Boot (Men)
MADDEN

Tristen Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(44)
Azzano Plain Toe Chukka Boot (Men)
Florsheim

Azzano Plain Toe Chukka 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
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)
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)
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)
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)
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)
Forge Lace-Up Boot (Men)
Florsheim

Forge Lace-Up Boot (Men)

$49.48Current Price $49.48
(Extra 40% off)Includes extra 40% off.
$82.47Previous Price $82.47
$135.00Comparable value $135.00
Price Drop
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)
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
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)
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)
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)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(119)
Claus Chukka Boot (Men)
Dune London

Claus Chukka Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
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)
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)
Breck Chukka Boot (Men)
Hawker Rye

Breck Chukka Boot (Men)

$14.99Current Price $14.99
(Extra 40% off)Includes extra 40% off.
$24.99Previous Price $24.99
$89.00Comparable value $89.00
Price Drop
(1)
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
(17)
Estiban Chelsea Boot (Men)
MADDEN

Estiban Chelsea Boot (Men)

$54.97Current Price $54.97
(35% off)35% off.
$85.00Comparable value $85.00
(5)
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)
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)
Bradley Water Repellent Leather Boot (Men)
Hey Dude

Bradley Water Repellent Leather Boot (Men)

$49.97Current Price $49.97
(47% off)47% off.
$94.99Comparable value $94.99
(25)
Dustin Boot (Men)
Dockers®

Dustin Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(2)
Lockhart Mini Lug Suede Chelsea Boot (Men)
New
Nordstrom

Lockhart Mini Lug Suede Chelsea Boot (Men)

$49.97Current Price $49.97
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)
Karnak Water Resistant Plain Toe Boot (Men)
NUNN BUSH

Karnak Water Resistant Plain Toe Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
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)
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
(7)
Thomas Lace-Up Boot (Men)
Dockers®

Thomas Lace-Up Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(4)
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
'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)
Lyle Chelsea Boot (Men)
VINTAGE FOUNDRY

Lyle Chelsea Boot (Men)

$41.98 – $44.97Current Price $41.98 to $44.97
(Extra 40% off)Includes extra 40% off.
$69.98 – $74.96Previous Price $69.98 to $74.96
$200.00Comparable value $200.00
Price Drop
(3)
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)
Esmond Chukka Boot (Men)
Dockers®

Esmond Chukka Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Maplewalk Rise Boot (Men)
Clarks®

Maplewalk Rise 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
$120.00Comparable value $120.00
Price Drop
Maplewalk Moc Toe Boot (Men)
Clarks®

Maplewalk Moc Toe Boot (Men)

$79.97Current Price $79.97
(33% off)33% off.
$120.00Comparable value $120.00
(6)
Otto Chukka Boot - Wide Width Available (Men)
NUNN BUSH

Otto Chukka Boot - Wide Width Available (Men)

$20.23 – $79.97Current Price $20.23 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$33.72Previous Price $33.72
$95.00 – $110.00Comparable value $95.00 to $110.00
Price Drop
(14)
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)
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
Truman Chelsea Boot (Men)
Dockers®

Truman Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Telford Lace-Up Boot (Men)
Dockers®

Telford Lace-Up Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
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)
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
Pampa Sport Waterproof Boot (Men)
Palladium

Pampa Sport Waterproof Boot (Men)

$49.97Current Price $49.97
(70% off)70% off.
$170.00Comparable value $170.00
(1)
x John Deere Relaxed Fit Terraform Waterproof Boot (Men)
SKECHERS

x John Deere Relaxed Fit Terraform Waterproof Boot (Men)

$59.97Current Price $59.97
(55% off)55% off.
$135.00Comparable value $135.00
(9)
Only a few left
Waylon Lace-Up Boot (Men)
New
Lee

Waylon Lace-Up Boot (Men)

$74.97Current Price $74.97
(25% off)25% off.
$100.00Comparable value $100.00
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)
Killington Trekker Mid Boot (Men)
Timberland

Killington Trekker Mid Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(1)
Only a few left
Peter Boot (Men)
Steve Madden

Peter Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
(3)
Sesame Chelsea Boot (Men)
New
Tommy Hilfiger

Sesame Chelsea Boot (Men)

$54.97Current Price $54.97
(53% off)53% off.
$119.00Comparable value $119.00
(34)
Langton Chelsea Boot (Men)
ALDO

Langton Chelsea Boot (Men)

$74.97Current Price $74.97
(50% off)50% off.
$150.00Comparable value $150.00
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
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
Taskorn Combat Boot (Men)
MADDEN

Taskorn Combat Boot (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(46)
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)
Taskorn Combat Boot (Men)
MADDEN

Taskorn Combat Boot (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(9)
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
(5)
Redlodge Mid Hiking Sneaker (Men)
Eddie Bauer

Redlodge Mid Hiking Sneaker (Men)

$52.97Current Price $52.97
(33% off)33% off.
$79.99Comparable value $79.99
(1)
Only a few left
Nash Chelsea Boot (Men)
Abound

Nash Chelsea Boot (Men)

$59.97Current Price $59.97
(33% off)33% off.
$89.95Comparable value $89.95
Knighton Boot (Men)
ALDO

Knighton Boot (Men)

$23.38 – $29.99Current Price $23.38 to $29.99
(Extra 40% off)Includes extra 40% off.
$38.98 – $49.99Previous Price $38.98 to $49.99
$130.00 – $150.00Comparable value $130.00 to $150.00
Price Drop
(2)
Madson II Moc Toe Waterproof Boot (Men)
New
SOREL

Madson II Moc Toe Waterproof Boot (Men)

$79.97 – $99.97Current Price $79.97 to $99.97
(Up to 60% off)Up to 60% off.
$200.00Comparable value $200.00
(33)
Only a few left
Wilder Chelsea Boot (Men)
Abound

Wilder Chelsea Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$79.95Comparable value $79.95
(6)
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)
Roklan Chelsea Boot (Men)
Tommy Hilfiger

Roklan Chelsea Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.00Comparable value $129.00
Thames Chukka Boot (Men)
Ben Sherman

Thames Chukka Boot (Men)

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
101 Lace-Up Boot (Women)
New
Dr. Martens

101 Lace-Up Boot (Women)

$79.97Current Price $79.97
(46% off)46% off.
$150.00Comparable value $150.00
(2)
'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)
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
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
(3)
Berton Chelsea Boot (Men)
Tommy Hilfiger

Berton Chelsea 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
Only a few left
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)
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