Most combat boots have a break in period that can be very uncomfortable. Definitely bring moleskin to prevent blisters and wear good socks (just search padded boot socks) if you go this route. Bring an extra pair of comfortable waking shoes in case the boots hurt too much.

Consider hiking boots if you’re buying new because they tend to break in a lot faster and are way more comfortable for walking around.

I’ll be wearing my doc martens for a few outfits and alternating with some memory foam sketchers to give my feet a break.