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Men's Boots Under $100

  • All Boots
  • Chelsea
  • Chukka
  • Combat & Lace-Up
  • Comfort
  • Dress Boots
  • Rain & Snow
  • Boots Under $100
290 items
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)
Steel Toe Work Boot (Men)
AVALANCHE

Steel Toe Work Boot (Men)

$59.97Current Price $59.97
(25% off)25% off.
$79.99Comparable value $79.99
(2)
Park Hiker Shoe (Men)
GREATS

Park Hiker Shoe (Men)

$69.97Current Price $69.97
(72% off)72% off.
$250.00Comparable value $250.00
Carson Hybrid Chukka Boot (Men)
Allen Edmonds

Carson Hybrid Chukka Boot (Men)

$58.48 – $149.97Current Price $58.48 to $149.97
(Extra 40% off select items)Includes extra 40% off select items.
$97.48 – $99.99Previous Price $97.48 to $99.99
$345.00Comparable value $345.00
Price Drop
(30)
Hybrid Low Boy Chelsea Boot (Men)
Ariat

Hybrid Low Boy Chelsea Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$159.95Comparable value $159.95
(27)
Fowler Waterproof Snow Boot (Men)
POLAR RANGE

Fowler Waterproof Snow Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(2)
Only a few left
Neumel Shaggy Suede Chukka Boot (Men)
UGG®

Neumel Shaggy Suede Chukka Boot (Men)

$71.22Current Price $71.22
(52% off)52% off.
$150.00Comparable value $150.00
New Markdown
(2)
Neumel High Weather Hybrid Waterproof Boot (Men)
UGG®

Neumel High Weather Hybrid Waterproof Boot (Men)

$64.98Current Price $64.98
(69% off)69% off.
$210.00Comparable value $210.00
New Markdown
(7)
Tristen Boot (Men)
MADDEN

Tristen Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(44)
P-Ely Wingtip Boot (Men)
Steve Madden

P-Ely Wingtip Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
Chelsea Boot (Men)
KARL LAGERFELD PARIS

Chelsea Boot (Men)

$89.97Current Price $89.97
(77% off)77% off.
$395.00Comparable value $395.00
(2)
Cosy Genuine Shearling Extra Short Bootie (Men)
Australia Luxe Collective

Cosy Genuine Shearling Extra Short Bootie (Men)

$99.97Current Price $99.97
(58% off)58% off.
$240.00Comparable value $240.00
Only a few left
Grand Remix Chukka Boot (Men)
Cole Haan

Grand Remix Chukka Boot (Men)

$99.97Current Price $99.97
(Up to 56% off)Up to 56% off.
$220.00 – $230.00Comparable value $220.00 to $230.00
(15)
Yukkon Lace-Up Boot (Men)
VANCE CO

Yukkon Lace-Up Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$109.99Comparable value $109.99
Dylan Chelsea Boot (Men)
Dockers®

Dylan Chelsea Boot (Men)

$59.97Current Price $59.97
(36% off)36% off.
$95.00Comparable value $95.00
(5)
Edwin Weatherproof Lace-Up Boot (Men)
Aquatalia

Edwin Weatherproof Lace-Up Boot (Men)

$89.99 – $93.58Current Price $89.99 to $93.58
(Extra 40% off)Includes extra 40% off.
$149.99 – $155.98Previous Price $149.99 to $155.98
$575.00Comparable value $575.00
Price Drop
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)
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
'Daily Double' Chelsea Boot (Men)
Eastland

'Daily Double' Chelsea Boot (Men)

$44.97Current Price $44.97
(Extra 40% off)Includes extra 40% off.
$74.96Previous Price $74.96
$125.00Comparable value $125.00
Price Drop
(8)
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)
Hayden Faux Fur Lined Slipper (Men)
VANCE CO

Hayden Faux Fur Lined Slipper (Men)

$29.97Current Price $29.97
(33% off)33% off.
$44.99Comparable value $44.99
(3)
Brody Chelsea Boot (Men)
Johnston & Murphy

Brody Chelsea Boot (Men)

$69.97Current Price $69.97
(57% off)57% off.
$165.00Comparable value $165.00
(19)
Grand Chelsea Boot (Men)
Cole Haan

Grand Chelsea Boot (Men)

$32.98Current Price $32.98
(Extra 40% off)Includes extra 40% off.
$54.98Previous Price $54.98
$150.00Comparable value $150.00
Price Drop
Convoy Lace-Up Boot
LUGZ

Convoy Lace-Up Boot

$49.97 – $54.97Current Price $49.97 to $54.97
(Up to 37% off)Up to 37% off.
$80.00Comparable value $80.00
(1)
Clifton Waterproof Chelsea Duck Boot (Men)
Sperry

Clifton Waterproof Chelsea Duck Boot (Men)

$49.97Current Price $49.97
(54% off)54% off.
$110.00Comparable value $110.00
(1)
Rogue Lace-Up Boot (Men)
VANCE CO

Rogue Lace-Up Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$109.99Comparable value $109.99
Patterson Cap Toe Chukka Boot (Men)
Eastland

Patterson Cap Toe Chukka Boot (Men)

$26.97Current Price $26.97
(Extra 40% off)Includes extra 40% off.
$44.96Previous Price $44.96
$90.00Comparable value $90.00
Price Drop
Koen Chukka Boot (Men)
Mykos

Koen Chukka Boot (Men)

$74.97Current Price $74.97
(21% off)21% off.
$94.99Comparable value $94.99
Milford Duck Boot (Men)
JBU

Milford Duck Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(5)
Wynford Chelsea Boot (Men)
ALDO

Wynford Chelsea Boot (Men)

$74.97Current Price $74.97
(50% off)50% off.
$150.00Comparable value $150.00
Thames Chukka Boot (Men)
Ben Sherman

Thames Chukka Boot (Men)

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
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)
Bradley Chelsea Boot (Men)
Stacy Adams

Bradley Chelsea Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
Estiban Chelsea Boot (Men)
MADDEN

Estiban Chelsea Boot (Men)

$54.97Current Price $54.97
(35% off)35% off.
$85.00Comparable value $85.00
(5)
Jimmy Plain Toe Vegan Leather Chukka Boot (Men)
VANCE CO

Jimmy Plain Toe Vegan Leather Chukka Boot (Men)

$39.99Current Price $39.99
(63% off)63% off.
$109.99Comparable value $109.99
Only a few left
Ruvo Chelsea Boot (Men)
Florsheim

Ruvo Chelsea Boot (Men)

$49.48Current Price $49.48
(Extra 40% off)Includes extra 40% off.
$82.47Previous Price $82.47
$150.00Comparable value $150.00
Price Drop
(22)
Osmond Chelsea Boot (Men)
VANCE CO

Osmond Chelsea Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$109.99Comparable value $109.99
(1)
Fenton Lug Sole Chelsea Boot (Men)
Steve Madden

Fenton Lug Sole Chelsea Boot (Men)

$29.99 – $79.97Current Price $29.99 to $79.97
(Extra 40% off select items)Includes extra 40% off select items.
$49.99Previous Price $49.99
$130.00Comparable value $130.00
Price Drop
(6)
Moc Toe Boot (Men)
Dockers®

Moc Toe Boot (Men)

$64.97Current Price $64.97
(31% off)31% off.
$95.00Comparable value $95.00
(4)
Blaise Ankle Boot (Men)
VINTAGE FOUNDRY

Blaise Ankle Boot (Men)

$99.97Current Price $99.97
(62% off)62% off.
$269.00Comparable value $269.00
Only a few left
Arctic Waterproof Faux-Fur Lined Duck Toe Snow Boot (Men)
POLAR RANGE

Arctic Waterproof Faux-Fur Lined Duck Toe Snow Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(2)
Henson XC4 Waterproof Chukka Boot (Men)
Johnston & Murphy

Henson XC4 Waterproof Chukka Boot (Men)

$99.97Current Price $99.97
(49% off)49% off.
$199.00Comparable value $199.00
(18)
Finn Plain Toe Boot (Men)
Eastland

Finn Plain Toe Boot (Men)

$26.97Current Price $26.97
(Extra 40% off)Includes extra 40% off.
$44.96Previous Price $44.96
$90.00Comparable value $90.00
Price Drop
(2)
Landon Chelsea Boot - Wide Width (Men)
VANCE CO

Landon Chelsea Boot - Wide Width (Men)

$14.83 – $49.97Current Price $14.83 to $49.97
(Extra 40% off select items)Includes extra 40% off select items.
$24.73Previous Price $24.73
$84.99Comparable value $84.99
Price Drop
(11)
Chelsea Boot (Men)
KARL LAGERFELD PARIS

Chelsea Boot (Men)

$89.97Current Price $89.97
(77% off)77% off.
$395.00Comparable value $395.00
(1)
Only a few left
Zebzag 4-Eye Lace-Up Boot (Men)
New
Dr. Martens

Zebzag 4-Eye Lace-Up Boot (Men)

$89.97Current Price $89.97
(43% off)43% off.
$160.00Comparable value $160.00
Marshall Chelsea Boot - Wide Width Available (Men)
VANCE CO

Marshall Chelsea Boot - Wide Width Available (Men)

$59.97Current Price $59.97
(40% off)40% off.
$99.99Comparable value $99.99
(9)
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
Karnak Water Resistant Moc Toe Boot (Men)
NUNN BUSH

Karnak Water Resistant Moc Toe Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(3)
Camden Chelsea Boot (Men)
Dockers®

Camden Chelsea Boot (Men)

$59.99Current Price $59.99
(29% off)29% off.
$85.00Comparable value $85.00
Otis II Chelsea Boot (Men)
NUNN BUSH

Otis II Chelsea Boot (Men)

$89.97Current Price $89.97
(18% off)18% off.
$110.00Comparable value $110.00
(1)
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)
Questo Brogue Combat Boot (Men)
La Milano

Questo Brogue Combat Boot (Men)

$79.97Current Price $79.97
(1)
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
(3)
Cryus Chelsea Boot (Men)
Eastland

Cryus Chelsea Boot (Men)

$26.97 – $26.98Current Price $26.97 to $26.98
(Extra 40% off)Includes extra 40% off.
$44.96 – $44.97Previous Price $44.96 to $44.97
$90.00Comparable value $90.00
Price Drop
(11)
Jenson Chelsea Boot (Men)
Johnston & Murphy

Jenson Chelsea Boot (Men)

$81.88Current Price $81.88
(Extra 40% off)Includes extra 40% off.
$136.48Previous Price $136.48
$328.00Comparable value $328.00
Price Drop
(4)
Fegan Cap Toe Boot (Men)
VANCE CO

Fegan Cap Toe Boot (Men)

$59.97Current Price $59.97
(45% off)45% off.
$109.99Comparable value $109.99
(1)
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)
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)
Chimney Pond Chelsea Boot (Men)
Eastland

Chimney Pond Chelsea Boot (Men)

$41.97 – $44.97Current Price $41.97 to $44.97
(Extra 40% off)Includes extra 40% off.
$69.96 – $74.96Previous Price $69.96 to $74.96
$145.00Comparable value $145.00
Price Drop
Spitfire Leather Chukka Boot (Men)
New
Ariat

Spitfire Leather Chukka Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$139.95Comparable value $139.95
(46)
Memille Chelsea Boot (Men)
Steve Madden

Memille Chelsea Boot (Men)

$20.99Current Price $20.99
(Extra 40% off)Includes extra 40% off.
$34.99Previous Price $34.99
$85.00Comparable value $85.00
Price Drop
(1)
Studded Chelsea Boot (Men)
KARL LAGERFELD PARIS

Studded Chelsea Boot (Men)

$89.97Current Price $89.97
(81% off)81% off.
$495.00Comparable value $495.00
(2)
Norwich Chelsea Boot (Men)
Ted Baker

Norwich Chelsea Boot (Men)

$89.97Current Price $89.97
(52% off)52% off.
$190.00Comparable value $190.00
Allagash Standard Derby Boot (Men)
Eastland

Allagash Standard Derby Boot (Men)

$38.98 – $41.97Current Price $38.98 to $41.97
(Extra 40% off)Includes extra 40% off.
$64.98 – $69.96Previous Price $64.98 to $69.96
$145.00Comparable value $145.00
Price Drop
Float Waterproof Rain Boot (Men)
Sperry

Float Waterproof Rain Boot (Men)

$16.77Current Price $16.77
(Extra 40% off)Includes extra 40% off.
$27.96Previous Price $27.96
$95.00Comparable value $95.00
Price Drop
(7)
Only a few left
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
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
Bodie Cowboy Boot (Men)
New
Ariat

Bodie Cowboy Boot (Men)

$99.97Current Price $99.97
(44% off)44% off.
$179.95Comparable value $179.95
(9)
Toney Waterproof Wingtip Boot (Men)
ALDO

Toney Waterproof Wingtip Boot (Men)

$79.97Current Price $79.97
(23% off)23% off.
$105.00Comparable value $105.00
Only a few left
Blast Waterproof Snow Duck Boot (Men)
POLAR RANGE

Blast Waterproof Snow Duck Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
Britton Road Mid Gore-Tex® Waterproof Boot (Men)
Timberland

Britton Road Mid Gore-Tex® Waterproof Boot (Men)

$58.48Current Price $58.48
(Extra 40% off)Includes extra 40% off.
$97.48Previous Price $97.48
$260.00Comparable value $260.00
Price Drop
Only a few left
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