Basically I'm looking for something with this type of design
Something fashionable that I could wear on a day to day basis but still of high enough quality that it could have utility in an outdoor/protest/combat situation. I'm pretty sure Doc Martens are kind of shit in the latter regard, no?
Also any other tips for owning boots? How difficult are they to break in? Are they going to cause my ankles to bleed? These would be my first pair. I'm not trying to go above $170 if possible.
I wore Belleville ultralights daily for four years in the Marines, about as comfy as sneakers and held up fine in the desert/jungle (on the admittedly rare occasions I went to those places). I also wore them while working out about once a week on average, and jumped in a pool with them about once a month on average, which didn't seem to be a problem. If you can find some in good condition at a thrift store or something, that would probably be the best deal.
Takes about a week of daily wear to break in. I suggest getting winter socks unless you live in a very hot environment, since the fluffiness acts as extra padding. Your ankles shouldn't bleed unless you have really thin socks.
Seconding Belleville. Those are some of the best quality boots I’ve ever worn, though I think they are pretty pricy last time I checked.