Timberland’s Cyber Monday 2025 event is expected to be a continuation of the brand’s Black Friday sale rather than a separate promotion. Based on recent trends, you can expect ongoing markdowns on boots, outerwear, and cold-weather essentials through the end of Cyber Monday. Here’s what we’re predicting for this year’s sale.
Expected Cyber Monday 2025 Sale Dates
Timberland’s Black Friday sale is projected to begin on Thursday, November 20, 2025 (that’s about a week before Thanksgiving). Like in previous years, the same deals are likely to carry through the long weekend and end late on Cyber Monday night, December 1, 2025.
Anticipated Discounts
You can expect 30% to 40% off select footwear and apparel during this period. These deals are usually available both in stores and online at timberland.com, with free shipping and returns included. Exclusions typically apply to limited-edition items, gift cards, and certain outlet products.
Featured Deals from Last Year’s Sale
Here are examples of price drops seen during Timberland’s Black Friday and Cyber Monday 2024 sale, which give a good idea of what you might find again this year:
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Women’s White Ledge Tall Lace-Up Waterproof Snow Boot – Reg. $150, dropped to around $84 (30% off)
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Men’s Chillberg Waterproof Insulated Boot – Reg. $150, dropped to $91 (30% off)
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Women’s Skyla Bay 2.0 Warm Lined Sneaker – Reg. $60, dropped to $35 (30% off)
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Men’s High Pile Fleece Lined Plaid Overshirt – Reg. $120, dropped to $70 (30% off)
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Women’s Everleigh Lined Chelsea Boot – Reg. $170, dropped to $98 (30% off)
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Men’s Converge Waterproof Boot – Reg. $160, dropped to $98 (30% off)
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Men’s and Women’s Synthetic Insulated Puffer Jacket – Reg. $130, dropped to $91 (30% off)
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Women’s Fashion Clog – Reg. $65, dropped to $35 (30% off)
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Men’s Howker Recycled Down Puffer Jacket – Reg. $300, dropped to $175 (30% off)
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Women’s Everleigh Warm Lined Boot – Reg. $170, dropped to $98 (30% off)
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Men’s Polartec Full-Zip Fleece Jacket – Reg. $95, dropped to $42 (30% off)
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Corduroy Hoodie – Reg. $110, dropped to $35 (30% off)
Last Year’s Black Friday/Cyber Monday 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.
- 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.