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- 3-Eye Classic 1
- 6 Inch 1,098
- 6 Inch Boot 75
- 8 Inch 14
C
- Chukka Classic 14
- Converge 23
- Cortina Valley 15
E
- Euro Hiker 86
- Everleigh 16
F
- Field Boot 135
H
- Hiker Boot 11
M
- Maple Grove 20
- Mt. Maddsen 13
R
- Roll Top 16
S
- Super Boot 12
TB123061-231
Timberland Chukka Waterproof 'Wheat'
$116
TB023061-231
Timberland Chukka Waterproof 'Wheat'
$141
TB0A6DVD-EXU
Timberland Premium Waterproof Chukka Boot 'Espresso Pack'
$170
TB037042-214
Timberland Chukka Boot GORE-TEX 'Brown'
$286
50059001
Timberland Classic Waterproof Chukka Boot 'Black'
$140
TB0A6GDX-EW1
nonnative x Timberland Chukka Boot GORE-TEX 'Taupe'
$400
TB0A2QBX-231
BAPE x Timberland Chukka Classic Boot 'Wheat'
$711
TB0A2QBX-231-W
BAPE x Timberland Chukka Classic Boot Wide 'Wheat'
$697
TB022049-214
Timberland Chukka Boot 'Brown'
$255
TB0A2HA9-EXU
Timberland Wmns Stone Street Waterproof Chukka Platform Boot 'Espresso Pack'
—
TB0A17C9-001
Timberland Chukka Classic Waterproof Boots 'Triple Black'
—
TB0A1UJS-001
Timberland Tenmile Chukka Boot 'Black'
—
TB0A5TWB-K38
Timberland Supaway Chukka 'Light Beige'
—
TB023022
Timberland Waterproof Chukka 'Wheat Nubuck'
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How much do Timberland Chukka Classic Boots cost?
14 Timberland Chukka Classic Boots in men's and women's sizes sell new with the original box from $116 to $711; the typical pair is $255. 1 of them list under retail, one in ten of those is 10% off or more. Prices as of Oct 2026.