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.
wear them until they look worn. there are other less "trendy" brands of work boots (and i've heard that Timbs' durability has dipped in recent years anyway). I find Wolverines serviceable enough, but they're about the same quality. if you want actual "combat boots," any military surplus or uniform store will sell them.