It's a very good question and IMO, 90% is it's in the way you wear it and what it's worn with that makes the difference.
There are bags that I bought years ago that I wouldn't buy again. There again I used to carry a pink and white poodle night-dress case as a bag so you can see what the 10% is made up from. These are gone.
I still have my 'Medusa' denim bag from the '00s, a huge white angle wing form the '90s, a fully beaded 'Coca Cola' bag (these bags are having a revival) and some others, not sure I would buy them again now but they do come in to play when I'm in a special mood and I'm not in my advanced years yet. I have the wardrobe for when I do though.
There are bags that I bought years ago that I wouldn't buy again. There again I used to carry a pink and white poodle night-dress case as a bag so you can see what the 10% is made up from. These are gone.
I still have my 'Medusa' denim bag from the '00s, a huge white angle wing form the '90s, a fully beaded 'Coca Cola' bag (these bags are having a revival) and some others, not sure I would buy them again now but they do come in to play when I'm in a special mood and I'm not in my advanced years yet. I have the wardrobe for when I do though.