While I agree that paying a little extra for nicer footwear and clothing is beneficial in the long run, I feel like clothing maintenance is neglected from discussions like these. For instance, it seems like your boots are getting a lot of wear through your daily use. Are you regularly cleaning them and using protective coatings for the materials? Are you making sure that pebbles aren’t lodging into the soles? And are you only using one pair of boots day-in, day out? If so, consider purchasing two pairs of mid-priced boots and alternating their use. Not only does it give you more options fashion-wise, it reduces the frequency of wear on each pair and allows for a significantly longer useful life. Finally, don’t be shy about getting your boots repaired by a professional from time to time. Resoling and patching boots can significantly extend their use at lower cost than buying new each time.
As for pants, avoid the dryer at all costs if you can, as that is the number one killer of useful life there. Also, make sure the fit of the pants is comfortable and allows a decent range of motion. Even the best pants will tear if you feel the crotch straining whenever you take a step.