TB1A42FY-214
Timberland TiTAN EV 6 Inch Composite Toe Waterproof Work Boot 'Teak Brown'
$90
3027681-200
Under Armour Trek Loadout Waterproof 'Coyote Brown'
$95
TB1A64PG-033
Timberland White Ledge Waterproof Mid Hiker Boot 'Castle Grey'
$72
URAINXAN
New Balance Rainier GORE-TEX 'Turtledove'
$99
3027681-001
Under Armour Trek Loadout Waterproof 'Ultimate Black'
$81
CQ0186-001
Nike Rhyodomo Gore-Tex 'Black Anthracite'
$86
3027681-002
Under Armour Trek Loadout Waterproof 'Black Distant Grey'
$92
TB0A5YKD-231
Timberland Arbor Road 6 Inch Waterproof Boot 'Wheat'
$70
TB0A2G4S-231
Timberland Lincoln Peak Waterproof Mid 'Wheat'
$98
TB0A2DZ2-015
Timberland Lincoln Peak Waterproof 'Black White'
$89
TB0A5YJS-015
Timberland Arbor Road Waterproof Chukka 'Triple Black'
$55
TB0A2DZD-110
Timberland Lincoln Peak Waterproof 'Medium Grey'
$72
TB0A5Q82-231
Timberland TiTAN EV 6 Inch Composite Toe Waterproof Work Boot 'Wheat'
$99
TB0A28JA-H40
Timberland Mt. Major 2 Waterproof Mid Boot 'Brown'
$90
Which Men's Waterproof Leather Boots cost under $100?
14 Men's Waterproof Leather Boots sell new with the original box from $55 to $99; the typical pair is $89. 14 of them list under retail, one in ten of those is 60% off or more. Prices as of Oct 2026.