Actually people do ask if they bought a car used or new. The same thing with a home--it usually sparks conversation. Now personal clothes and accessories aren't usually discussed like cars and homes (and yes kids), but people do indeed ask.
Really???? 😵 I haven't had anyone ask me questions like this - ever. I'm genuinely puzzled. Why would anyone feel those questions are appropriate / why would the asker want this insight? If the car is nice, I'd say "GREAT car!" I wouldn't ask about how they sourced it unless I was in the market for that exact car / bag / etc. and wanted insight for my use.