Are you a real handbag person? I'd probably take an everyday one and a dress up one......but all my space would be taken up with shoes, so I'm probably not the best person to ask
I'd be taking my red Crumpler backpack, my RedCross fabric sling tote, a large neutral bag in maybe leather for day functions and outings which required a certain degree of tidiness, a small black clutch for formal night events (they tend to go with everything) and a nice medium sized bag in a lighter colour (i would take my cream and white one) if i needed to look presentable in a summer outfit. So for me about 5. the first two aren't really handbags... but this would cover all my daily needs.
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