Great thread with a lot of good advice and perspectives. Now during the pandemic, I rarely go out and when I do, I will pick whatever bag I fancy just for that quick outing. Pre-pandemic, I had a rotation system I used. I have a list on my phone of all my bags (categorized by designers, styles, if multiples of the same style, in the order of purchase). Then as I use each bag, I put a checkmark next to that bag on the list and I don’t use that bag again until I have used all my bags. I may use a bag for just a weekend or for a week or longer (I tend to use my shoulder bags/hobos longer than other styles since I am more of a hobo girl). I started this system a few years back because some of my bags weren’t being used often enough (like a green bag would mostly be used only on St Patrick’s Day, black bags would not be used during the summer, etc). This system is affectionately referred to “speed-dating my bags” since I will continuously “date” all my bags to assess compatibility

. This also helps me assess and evaluate my bags to see if they need to leave my collection. I realize this system may be considered too rigid or inconvenient for many but it works for me.