Caro, great question.
A while ago Angie had a post with her client Karen in which was mentioned that Karen does not have many bags and I was so relieved. Finally, a proof I was not alone in may ways.
I am a fewer-is-better sort of bag lady, I prefer all rounders whenever possible. Initially, in the past this attitude was driven by low budget. Over the years I thought I had to have more bags, those pretty accessories, that I can switch between depending on my mood, to reflect I know my way with bags and style etc. I experimented a bit after joining YLF, but now that I need mostly practical bag(s) I've pondered the other, dressier needs and realized that I prefer one good, quality bag per season and that's it.
In total I have:
1 black crossbody - worn 80% time
1 red clossbody - worn 20% time
1 white crossbody bag - worn in the summer
1 small black crossbody - worn when I need free hands, but stil something to hold money, keys and phone in
1 small red crossbody - dressy and suitable for going out, but in reality hybernating
1 yellow and 1 red bag I used when I worked, which are now also hibernating as they are not practical for my current needs
1 cream slouchy bag, very roomy and practical for summer
a few small bags (evening clutches), currently unused
When I was clearing things out before our big move last summer I got rid of some bags, among them my all time favorite - black leather handmade bag that I got for my graduation. It was old and unsuitable for my style and lifestyle, a bit impractical too as it was rather heavy in itself, but it had served me well and taught me the value of a good, quality bag.