Features
AJ9277-220
Realtree x Nike SFB Gen 2 8 Inch GTX 'Fauna Brown'
$150
AQ1203-200
Realtree x Nike SFB Field 2 8 Inch GTX 'Dark Hazel'
$115
TB1A42FY-214
Timberland TiTAN EV 6 Inch Composite Toe Waterproof Work Boot 'Teak Brown'
$90
TB0A2JU5-W02
Timberland Moc Toe Mid Lace-Up GORE-TEX 'Black'
$168
3027681-200
Under Armour Trek Loadout Waterproof 'Coyote Brown'
$95
TB1A18A6-D47
Timberland Field Boot Mid Waterproof 'Chocolate'
$117
3026737-001
Under Armour HOVR Infil Waterproof Tactical Boot 'Black Pitch Grey'
$510
TB192615-214
Timberland Boondock 6 Inch Composite Toe Waterproof Work Boot 'Brown Oiled Distressed'
$196
TB1A64PG-033
Timberland White Ledge Waterproof Mid Hiker Boot 'Castle Grey'
$72
URAINXAN
New Balance Rainier GORE-TEX 'Turtledove'
$99
TB126038-001
Timberland 6 Inch Pro Steel Toe Waterproof 200G Insulated Boot 'Black'
$169
3026369-001
Under Armour HOVR Infil Waterproof Tactical Boot 'Black Pitch Grey'
$212
1183B995-001
Onitsuka Tiger HMR Peak GORE-TEX 'Black Leather'
$198
3027681-001
Under Armour Trek Loadout Waterproof 'Ultimate Black'
$81
CQ0186-001
Nike Rhyodomo Gore-Tex 'Black Anthracite'
$86
TB0A6E4H-EQ8
Timberland Authentic Handsewn 7 Eye Lug GORE-TEX Boot 'Dark Red'
$273
3027681-002
Under Armour Trek Loadout Waterproof 'Black Distant Grey'
$92
TB0A5YHH-212
Timberland Arbor Road Waterproof Chukka 'Medium Brown'
$232
TB092615-214
Timberland Boondock 6 Inch Composite Toe Waterproof Work Boot 'Brown Oiled Distressed'
$330
TB0A2JFC-269
Timberland 6 Inch Waterproof Field Boot 'Light Beige'
$115
TB0A41MW-EIW
Timberland 6 Inch Heritage Premium Waterproof Boot 'Root Beer'
$247
TB0A5YJ5-231
Timberland Arbor Road Waterproof Chukka 'Wheat'
$192
TB0A5YM1-212
Timberland Arbor Road 6 Inch Waterproof Boot 'Medium Brown'
$247
TB0A6DVD-EXU
Timberland Premium Waterproof Chukka Boot 'Espresso Pack'
$170
3026369-200
Under Armour HOVR Infil Waterproof Tactical Boot 'Coyote'
$153
CQ0186-300
Nike Rhyodomo Gore-Tex 'Deepest Green Gum'
$118
TB0A2NU3-EM4
Timberland 6 Inch Heritage Premium Waterproof Boot 'Black Pioneers'
$130
TB0A5YKD-231
Timberland Arbor Road 6 Inch Waterproof Boot 'Wheat'
$70
TB0A42SR-001
Timberland 6 Inch Fleece Lined Waterproof Boot 'Black Gold'
$199
50059001
Timberland Classic Waterproof Chukka Boot 'Black'
$140
TB0A6FTA-EXU
Timberland 1973 Newman Waterproof Chukka Boot 'Espresso Pack'
$197
TB0A2G6D-015
Timberland Lincoln Peak Waterproof Mid 'Triple Black'
$152
TB0A6FTX-W02
Supreme x Timberland Field Boot GORE-TEX 'Black'
$280
31190001
Dr. Martens 1460 Trinity Wintergrip Waterproof Boot 'Black'
$177
TB0A6724-015
Timberland Chillberg Waterproof Insulated Mid Boot 'Triple Black'
$150
TB0A2G4S-231
Timberland Lincoln Peak Waterproof Mid 'Wheat'
$98
TB0A29UP-001
Timberland Gridworks 6 Inch Waterproof Work Boot 'Black'
$152
TB0A6F8F-W02
JJJJound x Timberland 6 Inch Premium GORE-TEX 'Black'
$600
VN000D29BGS
Hana Beaman x Vans Standard Chelsea Mid Waterproof MTE 'Brown Green'
$122
TB1A44P1-015
Timberland Redwood Falls Waterproof Boot 'Black'
$201
TB06865B-210
Timberland Canard 2 Waterproof Oxford 'Medium Brown'
$106
TB0A2JU5-EM4
Aimé Leon Dore x Timberland Moc Toe Mid Lace-Up GORE-TEX 'Brown'
$699
1203A047-001
nonnative x ASICS Gel Yeti Tokyo High GORE-TEX 'Black'
$250
ALDHERITAGEMID-BLK
Aimé Leon Dore x Timberland Heritage Lace Up Mid GORE-TEX 'Black'
$599
VN000D29B7G
Vans Standard Chelsea Mid Waterproof MTE 'Brown Gum'
$110
TB0A2DZ2-015
Timberland Lincoln Peak Waterproof 'Black White'
$89
TB0A29TG-214
Timberland Pro Boondock HD 8 Inch Composite Toe Waterproof Work Boot 'Brown'
$147
TB038021-242
Timberland Direct Attach 6 Inch Steel Toe Waterproof Work Boot 'Brown'
$123
How much do Men's Waterproof Leather Boots cost?
82 Men's Waterproof Leather Boots sell new with the original box from $72 to $699; the typical pair is $152. 31 of them list under retail, one in ten of those is 45% off or more. Prices as of Oct 2026.