Timberland Waterproof Classic Chukka By mhydock on Jan 05, 2008 - Updated Sep 18, 2011

I have owned and gladly worn the Timberland Waterproof Classic Chukka in the black smooth leather for quite a few years now. The chukka boot is a half boot which can lend itself to being a bit dressier than the taller Timberland boots. The leather is initially stiff but after you wear them a few times it eases and they feel great. These are very durable boots. I have had a pair last almost 4 years now and I am not gentle with them. The only problem I have had with them is on the inside of the heel area. The fabric inner tends to wear away after a few years and can cause some discomfort but a little cushion and tape and you are on your way. I cannot stress how great these boots are not only in style but in comfort. Even after a few years, I still wear mine on a weekly basis.