I don't think anyone should ever be made to feel bad about their possessions, no matter what state the economy is in. I wear my Birkins wherever I feel safe to wear them, and if someone feels bad because of it, that's their problem, not mine. I often see people with things I can't afford (jewellery, cars, etc.) and I will continue to see these things, and it's something I have to accept. It's something virtually everyone has to accept-- there will always be someone with more, and someone with less, no matter how much or little you have.
I think the only real concern is safety; there are lots of places (both here at home and abroad) where I wouldn't dream of carrying an H-bag because I would be afraid of something happening. You always need to be aware of both your personal safety, and the safety of your items-- even if they are insured, sometimes H bags can be a pain in the ass to replace! That said, I find that in the majority of places, no one even looks twice at my Birkins, especially the black one. We here on the forum are so keenly attuned to anything H that we can spot an H bag or a fake at fifty paces, and it may have rubbed off on our SOs and good friends, but the "real world", in general, has no clue what you're carrying or how much it's worth!