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
TB02730R-242
Timberland Mt. Maddsen Mid Hiker 'Dark Brown'
$58
TB1A18RI-231
Timberland Field Boot Mid Waterproof 'Wheat'
$85
TB050059-001
Timberland 1973 Newman Premium Chukka Boot 'Black'
$75
TB150059-001
Timberland 1973 Newman Premium Chukka Boot 'Black'
$55
TB0A2PUSAAD
Timberland Road Trip Euro Hiker Boot 'Rust Dark Grey'
$97
TB1A17KY-001
Timberland Field Boot Mid Waterproof 'Black'
$85
TB0A28A2-W05
Timberland Euro Hiker Mid 'Black'
$99
TB0A6DB3-EK5
Timberland Motion Access Mid Waterproof Boot 'Black'
$95
TB0A28GY-754
Timberland Euro Hiker Boot 'Wheat Beige'
$93
TB0A5ZHH-A58
Timberland Euro Hiker Mid 'Dark Green'
$87
TB0A5W6N-C60
Timberland Waterproof Field Boot 'Burgundy'
$85
TB0A2JFE085
Timberland 6 Inch Field Boot Premium 'Medium Grey'
$79
TB010028-214
Timberland Field Boot 'Sundance Brown'
$90
TB0A41AQ-F13
Timberland Adventure 2.0 Oxford 'Rust'
$70
TB0A5WAD-A58
Timberland Authentic 3 Eye Classic Boat Boot 'Dark Green'
$96
TB0A1Y6V-019
Timberland Adventure 2.0 Oxford 'Navy'
$70
TB0A2A3E-F13
Timberland Bradstreet Plain Toe Oxford 'Rust'
$90
TB1A5TF3-001
Timberland Sawhorse 6 Inch 'Black'
$50
TB0A1B9S
Timberland 6 Inch Premium Boot 'Forged Iron'
$87
TB0A2EJU-A58
Timberland Killington Ultra Low 'Dark Green'
$75
TB012122-001
Timberland White Legde Mid 'Black'
$75
TB0A5YKD-231
Timberland Arbor Road 6 Inch Waterproof Boot 'Wheat'
$70
TB0A2A38-033
Timberland Euro Hiker Mid 'Grey Black Green'
$98
TB06743A
Timberland Groveton Chukka
$59
TB0A2G4S-231
Timberland Lincoln Peak Waterproof Mid 'Wheat'
$98
TB0A1BBJ
Timberland 6 Inch Premium Perforated 'Veg Tan'
$83
TB012135-214
Timberland White Legde Mid 'Brown Full Grain'
$70
TB0A2DCG-F49
Timberland Field Trekker Mid 'Medium Grey'
$60
TB052562-214
Timberland Endurance CSA 6 Inch Steel Toe Work Boot 'Brown'
$89
TB010069-001
Timberland 6 Inch 'Black Smooth'
$85
TB0A5N9T-001
Timberland TBL Edge Boot 'Black'
$91
TB0A2DZ2-015
Timberland Lincoln Peak Waterproof 'Black White'
$89
TB0A176A-001
Timberland Pro Powertrain Sport Alloy Toe Work Sneaker 'Black'
$66
TB0A1617
Timberland Grantly Mountain Chukka 'Black'
$75
TB0A5TF3-001
Timberland Sawhorse 6 Inch 'Black'
$96
TB0A6CU8-001
Timberland 6 Inch Premium Boot 'Varsity Chenille - Black'
$70
TB0A6CJG-001
Timberland 6 Inch Premium Boot 'White Black'
$69
TB0A24C9
Timberland Waterproof Chukka 'Medium Brown'
$87
TB-0A1SES-F49
Timberland Davis Square Chukka 'Medium Grey'
$99
28569
Timberland Newmarket Chukka 'Navy Blue Red White'
$99
TB0A1LQA
Timberland Fly Roam Boot 'Redwood'
$70
TB0A1K1F
Timberland FlyRoam Sport Hiker
$83
TB0A28K6-015
Timberland Maple Grove Chukka 'Black Gum'
$78
Which Men's Timberland Sneakers cost under $100?
61 Men's Timberland Sneakers sell new with the original box from $55 to $99; the typical pair is $85. 44 of them list under retail, one in ten of those is 50% off or more. Prices as of Oct 2026.