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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
360 items
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
(1)
Theo Chukka Boot (Men)
Børn

Theo Chukka Boot (Men)

$59.97 – $79.97Current Price $59.97 to $79.97
(Up to 53% off select items)Up to 53% off select items.
$130.00Comparable value $130.00
(6)
Sawyer Chelsea Boot (Men)
Steve Madden

Sawyer Chelsea Boot (Men)

$49.97Current Price $49.97
(44% off)44% off.
$90.00Comparable value $90.00
(8)
Tristen Boot (Men)
MADDEN

Tristen Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$80.00Comparable value $80.00
(39)
Garner Chukka Boot (Men)
Hawker Rye

Garner Chukka Boot (Men)

$39.97Current Price $39.97
(55% off)55% off.
$89.00Comparable value $89.00
Taskorn Combat Boot (Men)
MADDEN

Taskorn Combat Boot (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(39)
Sesame Chelsea Boot (Men)
Tommy Hilfiger

Sesame Chelsea Boot (Men)

$54.97Current Price $54.97
(53% off)53% off.
$119.00Comparable value $119.00
(30)
Harbin Chukka Boot (Men)
Tommy Hilfiger

Harbin Chukka Boot (Men)

$59.97Current Price $59.97
(49% off)49% off.
$119.00Comparable value $119.00
(7)
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
NUNN BUSH

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

$44.97 – $54.97Current Price $44.97 to $54.97
(Up to 52% off)Up to 52% off.
$90.00 – $95.00Comparable value $90.00 to $95.00
(12)
2.Zerogrand Chukka Boot (Men)
Cole Haan

2.Zerogrand Chukka Boot (Men)

$99.97Current Price $99.97
(70% off)70% off.
$338.00Comparable value $338.00
(395)
Rodale Boot (Men)
Alesbury

Rodale Boot (Men)

$39.97Current Price $39.97
(52% off)52% off.
$85.00Comparable value $85.00
Peter Boot (Men)
New!
Steve Madden

Peter Boot (Men)

$89.97Current Price $89.97
(47% off)47% off.
$170.00Comparable value $170.00
(1)
Kenora Chukka Boot (Men)
ALDO

Kenora Chukka Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$130.00Comparable value $130.00
(1)
Borland Chelsea Boot (Men)
New!
Johnston & Murphy

Borland Chelsea Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
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
(1)
Hemet Chukka Boot (Men)
Steve Madden

Hemet Chukka Boot (Men)

$74.97Current Price $74.97
(42% off)42% off.
$130.00Comparable value $130.00
(3)
Taskorn Combat Boot (Men)
MADDEN

Taskorn Combat Boot (Men)

$54.97Current Price $54.97
(38% off)38% off.
$90.00Comparable value $90.00
(7)
Chalet Chelsea Boot (Men)
Florsheim

Chalet Chelsea Boot (Men)

$99.97Current Price $99.97
(31% off)31% off.
$145.00Comparable value $145.00
(111)
Bronnie Combat Boot (Men)
MADDEN

Bronnie Combat Boot (Men)

$59.97Current Price $59.97
(40% off)40% off.
$100.00Comparable value $100.00
(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
(1)
Treyton Chukka Boot (Men)
VINTAGE FOUNDRY

Treyton Chukka Boot (Men)

$99.97Current Price $99.97
(50% off)50% off.
$200.00Comparable value $200.00
(5)
Boswell Chukka Boot (Men)
Johnston & Murphy

Boswell Chukka Boot (Men)

$89.97Current Price $89.97
(48% off)48% off.
$175.00Comparable value $175.00
(10)
Upton Chukka Boot (Men)
New!
Johnston & Murphy

Upton Chukka Boot (Men)

$69.97Current Price $69.97
(58% off)58% off.
$169.00Comparable value $169.00
(18)
Calder Chukka Boot (Men)
Johnston & Murphy

Calder Chukka Boot (Men)

$79.97Current Price $79.97
(51% off)51% off.
$165.00Comparable value $165.00
(21)
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
Roklan Chelsea Boot (Men)
Tommy Hilfiger

Roklan Chelsea Boot (Men)

$59.97Current Price $59.97
(53% off)53% off.
$129.00Comparable value $129.00
Marlow Chukka Boot (Men)
VINTAGE FOUNDRY

Marlow Chukka Boot (Men)

$89.97Current Price $89.97
(51% off)51% off.
$185.00Comparable value $185.00
Chamberlin Grand Chukka Boot (Men)
Cole Haan

Chamberlin Grand Chukka Boot (Men)

$97.47 – $129.97Current Price $97.47 to $129.97
(Up to 66% off select items)Up to 66% off select items.
$290.00Comparable value $290.00
(1)
Wilder Chelsea Boot (Men)
Abound

Wilder Chelsea Boot (Men)

$49.97Current Price $49.97
(37% off)37% off.
$79.95Comparable value $79.95
(4)
Grand Chelsea Boot (Men)
Clear The Rack
Cole Haan

Grand Chelsea Boot (Men)

$41.23Current Price $41.23
(Extra 25% off)Includes extra 25% off.
$54.98Previous Price $54.98
$150.00Comparable value $150.00
Clark Road Hands-Free Slip-On Derby (Men)
Marc Joseph New York

Clark Road Hands-Free Slip-On Derby (Men)

$59.97 – $79.97Current Price $59.97 to $79.97
(Up to 63% off select items)Up to 63% off select items.
$165.00Comparable value $165.00
(1)
Lincoln Chukka (Men)
Børn

Lincoln Chukka (Men)

$89.97Current Price $89.97
(41% off)41% off.
$155.00Comparable value $155.00
(4)
Chase Moc Toe Boot (Men)
G.H.BASS

Chase Moc Toe Boot (Men)

$89.97 – $119.97Current Price $89.97 to $119.97
(Up to 69% off select items)Up to 69% off select items.
$295.00Comparable value $295.00
(2)
Jefry Chukka Boot (Men)
ALDO

Jefry Chukka Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
Devon Lace-Up Boot (Men)
Clear The Rack
RESERVE FOOTWEAR

Devon Lace-Up Boot (Men)

$33.74Current Price $33.74
(Extra 25% off)Includes extra 25% off.
$44.99Previous Price $44.99
$125.00Comparable value $125.00
(1)
Clydell Chukka Boot (Men)
Dune London

Clydell Chukka Boot (Men)

$99.97Current Price $99.97
(48% off)48% off.
$195.00Comparable value $195.00
Apron Toe Boot (Men)
Rush by Gordon Rush

Apron Toe Boot (Men)

$54.97Current Price $54.97
(56% off)56% off.
$125.00Comparable value $125.00
(9)
Dee Chukka Boot (Men)
Dockers®

Dee Chukka Boot (Men)

$39.97Current Price $39.97
(57% off)57% off.
$95.00Comparable value $95.00
Gerard Lug Sole Boot (Men)
RESERVE FOOTWEAR

Gerard Lug Sole Boot (Men)

$64.97Current Price $64.97
(48% off)48% off.
$125.00Comparable value $125.00
(3)
Combat Boot (Men)
Reaction Kenneth Cole

Combat Boot (Men)

$69.97Current Price $69.97
(50% off)50% off.
$140.00Comparable value $140.00
(1)
Brycee Lug Sole Boot (Men)
New!
MADDEN

Brycee Lug Sole Boot (Men)

$64.97Current Price $64.97
(35% off)35% off.
$100.00Comparable value $100.00
(1)
Faux Shearling Lined Double Buckle Boot (Men)
Clear The Rack
KARL LAGERFELD PARIS

Faux Shearling Lined Double Buckle Boot (Men)

$37.49Current Price $37.49
(Extra 25% off)Includes extra 25% off.
$49.99Previous Price $49.99
$225.00Comparable value $225.00
(16)
Chelsea Boot (Men)
Rush by Gordon Rush

Chelsea Boot (Men)

$49.97Current Price $49.97
(60% off)60% off.
$125.00Comparable value $125.00
(36)
Hugo Boot
Eastland

Hugo Boot

$44.97 – $59.97Current Price $44.97 to $59.97
(Up to 55% off select items)Up to 55% off select items.
$100.00Comparable value $100.00
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
Suede Chelsea Boot (Men)
KARL LAGERFELD PARIS

Suede Chelsea Boot (Men)

$89.97Current Price $89.97
(64% off)64% off.
$250.00Comparable value $250.00
(6)
Cap Toe Combat Boot (Men)
Rush by Gordon Rush

Cap Toe Combat Boot (Men)

$54.97Current Price $54.97
(56% off)56% off.
$125.00Comparable value $125.00
(6)
Austin Cap Toe Chukka Boot - Wide Width (Men)
VANCE CO

Austin Cap Toe Chukka Boot - Wide Width (Men)

$39.99Current Price $39.99
(55% off)55% off.
$89.99Comparable value $89.99
(2)
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
(14)
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)
Grand Atlantic Chukka Boot - Wide Width Available (Men)
Cole Haan

Grand Atlantic Chukka Boot - Wide Width Available (Men)

$74.97 – $99.97Current Price $74.97 to $99.97
(Up to 62% off select items)Up to 62% off select items.
$200.00Comparable value $200.00
(38)
Blaze Lace Cap Toe Boot (Men)
Tommy Hilfiger

Blaze Lace Cap Toe Boot (Men)

$59.97Current Price $59.97
(49% off)49% off.
$119.00Comparable value $119.00
Eli Suede Chukka Boot (Men)
Børn

Eli Suede Chukka Boot (Men)

$89.97Current Price $89.97
(30% off)30% off.
$130.00Comparable value $130.00
(1)
Hollow Zip Leather Boot (Men)
Clear The Rack
AllSaints

Hollow Zip Leather Boot (Men)

$84.35Current Price $84.35
(Extra 25% off)Includes extra 25% off.
$112.47Previous Price $112.47
$299.00Comparable value $299.00
(7)
Rilyn Chelsea Boot (Men)
Steve Madden

Rilyn Chelsea Boot (Men)

$79.97Current Price $79.97
(50% off)50% off.
$160.00Comparable value $160.00
(12)
High Fidelity Leather Boot (Men)
Eastland

High Fidelity Leather Boot (Men)

$79.97 – $119.97Current Price $79.97 to $119.97
(Up to 40% off)Up to 40% off.
$135.00Comparable value $135.00
(1)
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
(46)
Estiban Chelsea Boot (Men)
MADDEN

Estiban Chelsea Boot (Men)

$54.97Current Price $54.97
(35% off)35% off.
$85.00Comparable value $85.00
(4)
Steadwell Plain Toe Chukka Boot (Men)
Clarks®

Steadwell Plain Toe Chukka Boot (Men)

$79.97Current Price $79.97
(27% off)27% off.
$110.00Comparable value $110.00
Lennie Lug Sole Boot (Men)
MADDEN

Lennie Lug Sole Boot (Men)

$64.97Current Price $64.97
(35% off)35% off.
$100.00Comparable value $100.00
(6)
Attleboro Chelsea Boot (Men)
New!
Timberland

Attleboro Chelsea Boot (Men)

$69.97Current Price $69.97
(Up to 50% off)Up to 50% off.
$130.00 – $140.00Comparable value $130.00 to $140.00
(6)
Gonzal Lace-Up Boot (Men)
New!
Tommy Hilfiger

Gonzal Lace-Up Boot (Men)

$59.97Current Price $59.97
(55% off)55% off.
$135.00Comparable value $135.00
Grand Lug Sole Boot (Men)
Cole Haan

Grand Lug Sole Boot (Men)

$99.97Current Price $99.97
(25% off)25% off.
$135.00Comparable value $135.00
(2)
Frausen Lace-Up Boot (Men)
Hawker Rye

Frausen Lace-Up Boot (Men)

$39.97Current Price $39.97
(55% off)55% off.
$89.00Comparable value $89.00
Jaxon II Cap Toe Boot (Men)
New!
La Milano

Jaxon II Cap Toe Boot (Men)

$79.97Current Price $79.97
(20% off)20% off.
$99.99Comparable value $99.99
Berton Chelsea Boot (Men)
Tommy Hilfiger

Berton Chelsea Boot (Men)

$59.97Current Price $59.97
(49% off)49% off.
$119.00Comparable value $119.00
Barrett Water Resistant Boot (Men)
Johnston & Murphy

Barrett Water Resistant Boot (Men)

$99.97Current Price $99.97
(45% off)45% off.
$185.00Comparable value $185.00
(60)
Oakridge Lug Sole Boot (Men)
WINTHROP

Oakridge Lug Sole Boot (Men)

$59.97Current Price $59.97
(65% off)65% off.
$175.00Comparable value $175.00
(3)
Dominic Brogue Combat Boot (Men)
La Milano

Dominic Brogue Combat Boot (Men)

$79.97Current Price $79.97
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)
Payton Mini Lug Pebbled Leather Chukka Boot (Men)
Nordstrom

Payton Mini Lug Pebbled Leather Chukka Boot (Men)

$69.97Current Price $69.97
(46% off)46% off.
$129.95Comparable value $129.95
(12)
Only a few left
Lyle Chelsea Boot (Men)
VINTAGE FOUNDRY

Lyle Chelsea Boot (Men)

$74.97 – $99.97Current Price $74.97 to $99.97
(Up to 62% off select items)Up to 62% off select items.
$200.00Comparable value $200.00
(2)
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