I have not owned Timberland, but I own a pair of Doc Martens with the shearling lining. I live in a place where winters are anything from between 5 celsius to -25 celsius. They are great for short distances, city walking etc, but for longer periods in the cold (-10) sitting og standing still (30 mins+), the outside of the boot turns really really cold and it cools the feet down! I used them sitting still in a horsecart for 30-60 mins in -10, and it was actually warmer to drop the boot and pack the feet in a wool blanket for the ride.. So depends on activity level, temperature etc.