Updated on Thursday, November 20, 2025: Timberland’s Black Friday 2025 sale has officially kicked off, and will once again run through Cyber Monday. Here’s everything you need to know.
Key Details: When & Where
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Dates: The sale runs from November 20, 2025, through Cyber Monday, December 1, 2025.
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Availability: The deal applies to Timberland.com and Timberland Specialty Retail Stores in the U.S. only, so shoppers outside those channels may not be eligible.
The Deal: What’s the Discount & How It Works
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Discount Offered: 30% off select styles; the extra savings show up in your cart as “EXTRA 30% OFF!”.
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Stackable Offers: Because it applies on top of existing sale prices, you can lock in especially steep discounts on clearance boots, apparel, or accessories.
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Free Shipping: U.S. community members in the contiguous 48 states qualify for free standard shipping on orders over $75. If your order is below $75, standard shipping is just $5.
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Limitations: Not every Timberland piece or store is included. Exclusions may apply for limited-edition items, gift cards, or certain in-store outlets.
Highlighted Deals This Year
Here are some of the standout items currently eligible for the 30% discount:
- Women’s Mt. Maddsen Peak Waterproof Hiking Boot — $140 (after discount)
- Women’s Retro Swift High-Top Sneaker — $110
- Men’s Field Trekker Sneaker — $120
- Panel Leather Glove — $78
- Rib Knit Glove — $28
- Infant Crib Bootie — $45
- Direct Attach 8″ Waterproof Work Boot (Men’s) — $175
- Women’s Roxie Lane Mid Chelsea Boot — $140
- Men’s Redwood Falls Waterproof Boot — $145
- Women’s White Ledge Tall Waterproof Snow Boot — $160
- Insulated Chillberg Waterproof Winter Boot (Men’s) — $150
- 6-Inch Waterproof Field Boot (Men’s) — $190
- Women’s Winnick Waterproof 3-in-1 Jacket — $220
- Scar Ridge Waterproof Parka (Men’s) — $250
- Timberland PRO Hood Honcho Flame-Resistant Hoodie — ~$99.99
Timberland’s Black Friday/Cyber Monday 2025 Ad
Cyber Monday Ad History
We’ve built an archive of Timberland’s previous Cyber Monday ads over the years we’ve been tracking their sales. You can take a look and compare this year’s deals to those from the last few years by following the links below.
- 2025: Page 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 and 14.
- 2024: Page 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10.
- 2023: Page 1 and 2.
- 2022: Page 1, 2 and 3.
- 2021: Page 1 and 2.
- 2020: Page 1 and 2.
- 2019: Page 1.
- 2018: Page 1 and 2.
- 2017: Page 1.
- 2016: Page 1.
- 2015: Page 1.
- 2014: Page 1.
Questions & Comments
What are some of your favorite Timberland boots that you’re looking to get? Let us know in the comments.