

When the alarm goes off at 4am, your gear needs to be ready. Cold temperatures, wet ground and long hours in the stand demand equipment that works as hard as you do. For hunters who spend their weekdays on the job site and their weekends in the field, Timberland and Timberland PRO offer a practical approach to cold-weather comfort: dependable waterproof boots, hardworking layers and warmth without unnecessary bulk.

The difference is simple. Timberland (TREE) brings its outdoor footwear heritage to the ground, while Timberland PRO builds work-ready apparel designed to handle demanding days. Together, they make a versatile kit for the walk in, the cold sit and everything that happens between the field and the job site. Here are five boots and layers that will work as hard as you do.
Start from the ground up with the Timberland Chillberg Waterproof Insulated Boots in Wheat. Built for cold, wet conditions, these mid-height hiking boots combine waterproof protection with insulation to help keep your feet comfortable when temperatures drop. That makes them a strong foundation for early-morning sits, damp trails and chilly walks to the blind. The wheat color also fits naturally into a fall hunting kit without sacrificing everyday versatility.
For scouting routes, covering uneven ground and moving between outdoor work and weekend hunts, the Timberland Waterproof Field Boots deliver another dependable footwear option. Their waterproof construction is built for wet conditions, while the darker finish complements the earth tones of fall cover. They’re a practical choice for hunters who need footwear that can transition from the woods to everyday work without missing a beat.

When the temperature drops and sitting still becomes the hardest part of the hunt, reach for the Timberland PRO Fleece-Lined Shirt Jacket. This is the layer to build around for colder mornings, bringing extra warmth to a kit designed for long days outside. Its workwear-inspired design also makes it a natural fit for time spent on the job site. Wear it as a primary outer layer when conditions allow or build it into a heavier system when the cold really settles in.
Not every fall morning stays cold. The Timberland PRO Fleece-Lined Twill Vest adds core warmth while leaving your arms free to move. Layer it over a flannel for the walk in, wear it under a shell when the weather turns, or keep it handy for those days when temperatures climb after sunrise. It’s an adaptable option for hunters who want insulation without committing to a heavier jacket.
For the final layer, the Timberland PRO Fleece-Lined Yukon Flannel Shirt Jacket brings together familiar flannel style and added warmth. It’s a useful middle layer for the hike to your spot, the drive before daylight or a full day of outdoor work. Wear it alone in milder conditions or layer it beneath the shirt jacket or vest as temperatures change.

A successful cold-weather setup starts with the right combination of protection and flexibility. Timberland waterproof boots help handle wet ground, while Timberland PRO layers give you options as temperatures shift throughout the day. Start with the Chillberg boots for cold, wet mornings, add the Yukon Flannel for adaptable warmth, and build up with the fleece-lined shirt jacket or vest as needed.
Built for work. Ready for the field. With Timberland’s outdoor footwear heritage and Timberland PRO’s workwear-focused approach, this five-piece lineup gives hunters a practical foundation for the season ahead.