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.
If you're looking at Docs then get a pair of Solovairs instead. They use the original Doc's design which is a lot sturdier, and they can be resoled.
Otherwise maybe try some Corcoran Jump Boots or a pair of Redwings. Have used all of these at one point or another as motorbike boots but also as something to wear about the place once I've hopped off the bike.
Alternatively you could go for a pair of Redbacks or Blundstones. Think they're cattle wrangling boots for the Australian outback originally. Very comfy and sturdy, and some are even waterproof. They look nice too. I see lots of trendy people wearing them with all sorts of outfits.
Alternatively to that - builders boots. I've had a pair of DeWalt steel toecapped boots for ages now and they've taken me through warehousing and building jobs, up mountains, and just as a nice rugged fashion item. Also wore them on the bike, but ended up staining the toes black from the oil and urban muck.