I'm really lucky. I live in an area where people are just "nice". I've lived in other areas of the U.S., (NY, TX, CA) and people here are just friendly folk compared.
So, I get a lot of compliments on my bags without regard to brand. The ones that get the most compliments are my
Teal Nubuck
Gucci Soho Chain Medium (tote) Shoulder Bag (I just got this and can't walk 2 steps without people cooing over it!)
Red Leather Gucci Soho Small Chain Shoulder Bag (I even got a ton of compliments IN the Guccu store when I went to pick up my sale bags!)
Cobalt Blue Patent leather studded Beijo Tote (this cheapy still gets a loooooot of compliments any time I wear it)
Pink Suede Diane Von Furstenberg Harper (it's girly, it has a tassel...what's not to love!)
So, where I live, it's not a function of cost or brand - the majority of people just don't care. There is a lot of old money that is "over" the keeping up with the Joneses and we don't have a crazy competitive environment like a NY where you have to have "this" bag to fit in. It's really more a function of visual impact. No one says a peep about my Black Patent Chanel Classic Flap Jumbo or my
Prada bags when I'm wearing them. And, people with generations of wealth are just as likely to show up at a fundraiser in a handmade etsy bag as a Hermes.