Answering this just in terms of bags I do have:
I don't have any valuable bags I don't carry. I do, however, have a ton of cheap bags I'm very attached to that turned out to be impractical or goofy looking to carry - mostly bought on vacation to cheap places. Some of these I regret buying and some I definitely do not:
- Colorblocked suede envelope clutch in green, white, teal - Vietnam
- Large colorblocked suede envelope clutch / shoulder bag in red, orange, brown, ivory - Vietnam
- Ridiculous canvas / upcycled milk pouches saddlebag - Vietnam
- Camel-tone leather boston bag from small leather goods maker in Ethiopia
- Fabric tote - India
The envelopes are from Vietnam; fantastic leather, but terrible strap quality; I am thinking of cutting them off and replacing with chains or ribbons. The $10 upcycled mik pouch saddlebag, which is SO cute, I do regret: if I'd gotten a pouchette in same fabric instead, I'd be taking it everywhere. These are all taking up space in my closet. Souvenir bags are so impractical in actual life.