TB050009-648
Timberland 3-Eye Lug Handsewn Boat 'Burgundy'
$91
TB1A42FY-214
Timberland TiTAN EV 6 Inch Composite Toe Waterproof Work Boot 'Teak Brown'
$90
TB02731R-001
Timberland Mt. Maddsen Mid Hiker 'Black'
$55
TB1A64PG-033
Timberland White Ledge Waterproof Mid Hiker Boot 'Castle Grey'
$72
TB0A17KY-001
Timberland Field Boot 'Black'
$97
TB050059-001
Timberland 1973 Newman Premium Chukka Boot 'Black'
$75
TB150059-001
Timberland 1973 Newman Premium Chukka Boot 'Black'
$55
TB012122-001
Timberland White Legde Mid 'Black'
$75
TB0A5YKD-231
Timberland Arbor Road 6 Inch Waterproof Boot 'Wheat'
$70
TB0A2G4S-231
Timberland Lincoln Peak Waterproof Mid 'Wheat'
$98
TB052562-214
Timberland Endurance CSA 6 Inch Steel Toe Work Boot 'Brown'
$89
TB0A5N9T-001
Timberland TBL Edge Boot 'Black'
$91
TB0A2DZ2-015
Timberland Lincoln Peak Waterproof 'Black White'
$89
TB0A5TF3-001
Timberland Sawhorse 6 Inch 'Black'
$96
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
TB0A15WN-001
Timberland Mt. Abram Low 'Black'
$94
TB0A28JA-H40
Timberland Mt. Major 2 Waterproof Mid Boot 'Brown'
$90
Which Men's Leather Timberland Sneakers cost under $100?
19 Men's Leather Timberland Sneakers sell new with the original box from $55 to $99; the typical pair is $89. 18 of them list under retail, one in ten of those is 60% off or more. Prices as of Oct 2026.