there should be a guide on handbags on the website wiki.
the system is as fun as it is cumbersome.
I don't know what goes with what.
also its my ocd speaking but imagine being me, spending an hour going left and right, picking the best outfit within my budget, just to learn I cant wear it just cause i have to wear this handbag which I dont like the look of, but that handbag that looks nice doesnt go with any outfit that i would like, and my ocd just shortfuses then and there.
tldr: put a guide up on how handbags work.