I wore my boots as often as I could in a way that would incorporate them as I would normally go about my life. Being in in a walkable neighborhood, they were with me in countless trips the grocery, library, barbershop, park, laundromat, bank, hardware store, restaurants, office, and (my favorite) when I would take a walk after dinner. As for special occasions, the first week of wear coincided with the first time my mom visited from the Philippines so I broke in the boots showing her around San Francisco. I was also fortunate enough to take the boots to Providence in the winter where my wife had a grad school residency. There was no snow but it was cool to walk around a new city that had an old world feel to it.
The break in process went smoothly. Within the first week I walked around for maybe 2 miles a day and I didn’t encounter any discomfort. It probably helped that I had the thick black sign boot socks. The leather didn’t need much care. Just light brushing and wiping whenever I think they look like they need some brushing and wiping, which didn’t really happen a lot. To be honest, when I used some conditioner I think some of the effects of the teacore patina became less visible (or maybe they were just particular dirty, idk). Although my pair didn’t really show that much, it was pretty cool seeing the lighter brown spots showing some teacore patina.