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.
Really depends on the brand. A half size "too big" is a good idea because you will want to wear some thick socks inside if you're hiking a ways. A lot of hikers even wear a thin sock inside a thick sock.