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- 3-Eye Classic 1
- 6 Inch 609
- 6 Inch Boot 52
- 8 Inch 13
C
- Chukka Classic 13
- Converge 7
E
- Euro Hiker 60
F
- Field Boot 74
H
- Hiker Boot 11
M
- Maple Grove 20
- Mt. Maddsen 12
R
- Roll Top 12
S
- Super Boot 11
TB0A13F
Timberland Roll Top Boot 'Red'
$177
6635A
Timberland Roll Top Boot
$2,000
TB06634A
Timberland Basic Roll Top 'Wheat'
$193
TB0A1S6C-019
Timberland Roll Top Boot 'Navy'
$195
TB0A1QZA-231
Timberland Roll Top Boot 'Wheat Nubuck'
—
A191D
Timberland Roll Top F/F AF
—
TB0A28RH-231
Timberland Roll Top Boot 'Wheat Plaid'
—
TB0A1S5P-001
Timberland Roll Top Boot 'Black Nubuck'
—
TB0A28R6-001
Timberland Roll Top Boot 'Black Plaid'
—
A17QQ
Timberland Roll Top Boot
—
6223B
Timberland Roll Top 'Black'
—
TB0A11QV-242
Harris Tweed x Timberland Roll Top Boot 'Dark Brown'
—
How much do Men's Timberland Roll Top Boots cost?
12 Men's Timberland Roll Top Boots sell new with the original box from $177 to $2,000; the typical pair is $193. 0 of them list under retail. Prices as of Oct 2026.
- Timberland Roll Top Boot Red · $177
- Timberland Basic Roll Top Wheat · $193
- Timberland Roll Top Boot Navy · $195