Timberland are overpriced piece of junk nowadays, heavily marketed.
Even Panama Jacks are at a better prices.
For boots, it's better to find old stocks who can be repaired by the local shoe makers.
As for higher quality new boots, here we have a french shoemaker called "Le Soulor" and i would like to get the Montparnasse & Paloise models, which is ~500$ each