Hi All-
Timberland used to make high-quality outdoor gear, but they are aimed primarily at the college, hip-hop, and fashion markets as mentioned earlier. My personal feeling is that their current boots are junk. Their story is similar to that of Abercrombie & Fitch who previously had a reputable name for serious gear. Both of their product lines are currently positioned to handle the extreme rigors of mall shopping and music concerts.
Doc Martens are well-padded and would serve well if you're walking on hard, uniform surfaces like a concrete storeroom or warehouse. They do take a nice polish if so desired. You can also go with an "unconventional" look while wearing them. They even offer very funky versions like blue or green suede or even burgundy "patent" leather.
For honest-to-goodness performance, consider manufacturers like Danner, Merrell, Asolo, Raichle, Browning, and similar brands you'll find in a hiking/camping/hunting store. It is guaranteed you'll pay MUCH more when compared to the mall-type boots, but your overall cash outlay and ongoing comfort will more than offset this original investment.
Good luck with your search! Let us know what you select.
~ Blue Jays ~