The Timberland brand of shoes and boots was born in 1973, and has since been sold around the world. Timberland makes a full line of leather and synthetic work boots and hiking shoes, which can be stiff when new. Like most hiking shoes and boots, Timberlands require a break-in period before they become comfortable to wear. The same methods that will successfully break in Timberland boots and hikers can be used to break in most brands of work or hiking boots.
Wear your boots or hikers around the house as you perform everyday tasks Although you are just walking around the house, treat your Timberlands as though you are hiking a trail or putting in a day's work. Wear the same socks; tie them in the same way; line up your tongue, and flatten the gusset as you would when using the shoes for their intended purpose. The way the shoe is broken in is likely the way it will remain throughout its lifespan. Wear your Timberlands for longer and longer periods as they become increasingly soft and comfortable.
Wear your Timberlands around the neighborhood to further the breaking-in process. When your boots are comfortable enough to wear around the house without issue, wear them on errands and short walks. You'll be further softening the shoe material as well as conditioning your feet with longer and longer periods spent wearing your new Timberlands.
Hold the Timberlands in your hands, and bend the soles back and forth repeatedly to speed up the softening process. Squatting repeatedly while wearing Timberlands can also help soften the sole material.
Apply leather conditioner to the upper portions of your Timberlands according to the manufacturer's recommendations. Conditioning solution will help soften your Timberlands and eliminate pressure on your toes when walking.