LOL in the short time I have been here I can tell you you will get replies that are all over the map on that one!
There are people who do find it offensive that people who cannot afford to pay $1500 or $2000 for a bag should carry any bag that looks like one, even if THEY can tell the difference. They simply have some strong feelings about which, if any, bags people with lower incomes should use.
And then you will get me,
who will tell you that if you can get a bag whose look you like at Target for $10, why would you want to pay $300 for one that looks like it? I think that would be 30 of the $10 ones, but I'm not too good with numbers.
And yet other people who will tell you that the $300 bag is better quality, and yet others who will argue that it is better to spend the extra money quite independently of that.
So probably the best answer is, it depends on what you are hoping the bag will do. If you want it to hold things, and look good with a particular outfit, then you are not going to arrive at the same conclusion as someone who is hoping the bag will make a statement to all who recognize it that they have a bag by a particular designer, and/or a bag that costs a great deal of money.
When you think about it, there is plenty of cultural and historical precedent for that - in many cultures, it is customary for ladies to wear the entire family's wealth - even the wealth of an entire tribe or clan, in some cases - very visibly on her person, in the form of coins, jewelry, precious metals, etc. It's a time-honored human behavior - as is the idea that the poor should not be able to wear the same things as the nobility!
And it is also time-honored human behavior for some of us to do the ancient cultural equivalent of going to Target and getting the one for $10 because it is the perfect color to wear with our new gray (Lee) jeans!
Isaac Mizrahi said it best:
"That's what style is - not pleasing everybody"