A good, comfortable pair of boots can be hard to find. That's why we become attached to them and dread shopping for new ones. Plus, going shopping for clothes is boring as hell. Try a pair one, take it off, repeat, repeat, repeat. Put old shoes back on, go to different store, repeat. Boring as hell.
Bah. Comfort is relative and comes with time, anyway. I just buy boots that are, in some way, different from the ones I have. Usually taller. Or a different color. Diversity is the spice of life. Not that I like any diversity or spices when it comes to food, but for other areas, yes.
One buys 'em for more than just the aesthetics of the boot itself. Different boots change the way you walk, thus affecting other people's perceptions of you. This difference is seen in the comparison of sandals versus shoes versus combat boots versus knee-high boots. I dare you to walk grandiosely in a pair of flip-flops.
And at the end of the scale, there are wading/Zardoz boots. If you plan on wading rivers or raising a high level of WTFery, they are unsurpassed. One should take care if interviewing Sean Connery while wearing them. It could evoke painful memories.