Florsheim
Chalet Chelsea Boot (Men)
Current Price $99.97
31% off.
Comparable value $145.00
Men's Boots Under $100
BOSS
New Tunley Chelsea Boot (Men)
Current Price $89.97 to $149.97
Up to 54% off.
Comparable value $199.00
Ariat
Wexford Chelsea Boot (Men)
Current Price $99.97
47% off.
Comparable value $189.95
Tommy Hilfiger
Sesame Chelsea Boot (Men)
Current Price $54.97
53% off.
Comparable value $119.00
Clarks®
Shepton Chukka Boot (Men)
Current Price $74.97
Up to 31% off.
Comparable value $100.00 to $110.00
Nordstrom
Lockhart Mini Lug Suede Chelsea Boot (Men)
Current Price $49.97
58% off.
Comparable value $119.95
NUNN BUSH
Karnak Plain Toe Chelsea Boot (Men)
Current Price $58.48 to $89.97
Up to 51% off select items.
Comparable value $120.00
Ted Baker London
Norwich Chelsea Boot (Men)
Current Price $89.97
52% off.
Comparable value $190.00
Dr. Martens
Gender Inclusive 1460 Pascal Desert Brown Boot
Current Price $89.97
47% off.
Comparable value $170.00
Steve Madden
Rilyn Chelsea Boot (Men)
Current Price $59.96
62% off.
Comparable value $160.00
MADDEN
Sawyer Chelsea Boot (Men)
Current Price $32.48 to $49.97
Up to 63% off select items.
Comparable value $90.00
MADDEN
Estiban Chelsea Boot (Men)
Current Price $41.22
51% off.
Comparable value $85.00
Only a few left
NUNN BUSH
Otis II Chelsea Boot (Men)
Current Price $58.48 to $89.97
Up to 51% off select items.
Comparable value $110.00 to $120.00
Tommy Hilfiger
Gainsly Chelsea Boot (Men)
Current Price $59.97
52% off.
Comparable value $125.00
Abound
Wilder Chelsea Boot (Men)
Current Price $49.97
37% off.
Comparable value $79.95
VINTAGE FOUNDRY
Jimara Leather Faux Fur Lined Boot (Men)
Current Price $59.97
72% off.
Comparable value $220.00
LUGZ
Convoy Lace-Up Boot
Current Price $49.97 to $54.97
Up to 37% off.
Comparable value $80.00
Dune London
Cian Side Zip Boot (Men)
Current Price $89.97
52% off.
Comparable value $190.00
NUNN BUSH
Odell II Wingtip Boot (Men)
Current Price $89.97
18% off.
Comparable value $110.00
KARL LAGERFELD PARIS
Suede Zip Boot (Men)
Current Price $89.97
81% off.
Comparable value $495.00
Only a few left
Johnston & Murphy
Boswell Chukka Boot (Men)
Current Price $58.48 to $67.47
Up to 66% off.
Comparable value $175.00
Stacy Adams
Bradley Chelsea Boot (Men)
Current Price $89.97
43% off.
Comparable value $160.00
Birkenstock
Bend Chelsea Boot (Men)
Current Price $99.97
41% off.
Comparable value $170.00
Johnston & Murphy
Borland Chelsea Boot (Men)
Current Price $55.96 to $59.96
Up to 65% off.
Comparable value $160.00
VINTAGE FOUNDRY
Remington Combat Boot
Current Price $59.97
72% off.
Comparable value $220.00
Gino Vitale
Wingtip Chelsea Boot (Men)
Current Price $62.96 to $89.97
Up to 60% off select items.
Comparable value $159.99
Ariat
Sport Square Toe Western Boot (Men)
Current Price $99.97
47% off.
Comparable value $189.95
VINTAGE FOUNDRY
Lyle Chelsea Boot (Men)
Current Price $39.98 to $44.97
Up to 80% off.
Comparable value $200.00
VINTAGE FOUNDRY
Martin Chelsea Boot (Men)
Current Price $49.97
71% off.
Comparable value $175.00
Clarks® Originals
Wallabee Chukka Boot (Men)
Current Price $89.97
43% off.
Comparable value $160.00
adidas by Stella McCartney
ASMC Seeulater 2 Sneaker (Women)
Current Price $99.97
60% off.
Comparable value $250.00
Only a few left
Clarks®
Shepton Easy Chelsea Boot (Men)
Current Price $94.97
26% off.
Comparable value $130.00
Cole Haan
Grand Atlantic Chelsea Boot (Men)
Current Price $44.97 to $74.96
Up to 77% off.
Comparable value $200.00
Anthony Veer
Bushwick Chukka Boot (Men)
Current Price $74.97
48% off.
Comparable value $145.99
Call It Spring By Aldo
Volland Boot (Men)
Current Price $49.97
47% off.
Comparable value $94.99
Clarks®
Wallabee Genuine Calf Hair Chukka (Men)
Current Price $99.97
44% off.
Comparable value $180.00
Clarks®
Wallaston Chukka Boot (Men)
Current Price $59.96 to $79.97
Up to 50% off select items.
Comparable value $120.00
CARLOS SANTANA
Mantra Chelsea Boot (Men)
Current Price $99.97
28% off.
Comparable value $138.99
Ariat
Bodie Cowboy Boot (Men)
Current Price $99.97
44% off.
Comparable value $179.95
NUNN BUSH
Circuit Plain Toe Chukka Boot - Wide Width Available (Men)
Current Price $41.22 to $54.97
Up to 54% off select items.
Comparable value $90.00
VINTAGE FOUNDRY
Anderson Casual Chukka Boot (Men)
Current Price $69.97
60% off.
Comparable value $175.00
Cole Haan
Morse GRANDFØAM Chukka Boot (Men)
Current Price $84.48 to $97.47
Up to 61% off.
Comparable value $220.00
SOREL
Slabtown '62™ Waterproof Moc Toe Boot (Men)
Current Price $99.97
42% off.
Comparable value $175.00
La Milano
Jaxon II Cap Toe Boot (Men)
Current Price $79.97
20% off.
Comparable value $99.99
Only a few left
Steve Madden
Fenton Lug Sole Chelsea Boot (Men)
Current Price $49.99 to $59.96
Up to 61% off.
Comparable value $130.00
MADDEN
Taskorn Combat Boot (Men)
Current Price $54.97
38% off.
Comparable value $90.00
Dockers®
Telford Lace-Up Boot (Men)
Current Price $59.97
36% off.
Comparable value $95.00
MADDEN
Tristen Boot (Men)
Current Price $49.97
37% off.
Comparable value $80.00
Clarks®
Jaxen Easy Chelsea Boot (Men)
Current Price $99.97
16% off.
Comparable value $120.00
La Milano
Crest Cap Toe Chelsea Boot (Men)
Current Price $79.97
20% off.
Comparable value $99.99
Only a few left
Steve Madden
Scotch Lug Sole Boot (Men)
Current Price $49.98 to $59.96
Up to 61% off.
Comparable value $130.00
Thomas & Vine
Keegan Chukka Boot
Current Price $79.97
23% off.
Comparable value $104.97
KARL LAGERFELD PARIS
Studded Chelsea Boot (Men)
Current Price $89.97
81% off.
Comparable value $495.00
VINTAGE FOUNDRY
Hayden Boot (Men)
Current Price $39.97
85% off.
Comparable value $269.00
Johnston & Murphy
Brody Chelsea Boot (Men)
Current Price $49.99
69% off.
Comparable value $165.00
Florsheim
Chalet Leather Cap Toe Boot (Men)
Current Price $82.47
46% off.
Comparable value $155.00
NUNN BUSH
Chase Plain Toe Chukka Boot - Wide Width Available (Men)
Current Price $19.99 to $54.97
Up to 78% off select items.
Comparable value $95.00
Deer Stags
Garfield Plain Toe Chukka Boot (Men)
Current Price $64.97
35% off.
Comparable value $100.00
VITTORIO RUSSO
Wade Boot (Men)
Current Price $97.47
56% off.
Comparable value $225.00
VANCE CO
Marshall Chelsea Boot - Wide Width Available (Men)
Current Price $59.97
40% off.
Comparable value $99.99
ALDO
Zeddy Chelsea Boot (Men)
Current Price $84.97
43% off.
Comparable value $150.00
Rush by Gordon Rush
Chelsea Boot (Men)
Current Price $49.97
60% off.
Comparable value $125.00
Clarks®
Weltridge Side Zip Boot (Men)
Current Price $94.97
26% off.
Comparable value $130.00
VINTAGE FOUNDRY
Marlow Chukka Boot (Men)
Current Price $54.97
70% off.
Comparable value $185.00
Rodd & Gunn
Pebbly Hill Chukka Boot (Men)
Current Price $99.97
49% off.
Comparable value $198.00
Only a few left
Dr. Martens
2976 Wintergrip Water Resistant Chelsea Boot (Men)
Current Price $99.97
47% off.
Comparable value $190.00
Børn
Eli Suede Chukka Boot (Men)
Current Price $40.48 to $58.48
Up to 68% off.
Comparable value $130.00
Clarks®
Torhill Lo Chukka Boot (Men)
Current Price $69.97
46% off.
Comparable value $130.00
Merrell
Speed Strike 2 Hiking Boot (Men)
Current Price $84.97 to $89.97
Up to 25% off.
Comparable value $110.00 to $120.00
SOREL
Hi-Line Waterproof Lace-Up Boot (Men)
Current Price $62.96
65% off.
Comparable value $185.00
Vince
June Chukka Boot (Men)
Current Price $67.48
82% off.
Comparable value $375.00
Steve Madden
P-Ely Wingtip Boot (Men)
Current Price $89.97
47% off.
Comparable value $170.00