Silly me, I've always thought of a bag as a functional item to carry my stuff around. But I LOVE looking at bags, and recently realized I'm completely bag-impaired as far as knowing what goes with what (thanks to Rachylou's fashion quiz!). I could and have carried one bag. Granted, it's my gorgeous Karla's Closet Coach bag in black and goes with everything, but still - I'd like to add this skill o my repetoire.

How do you decide what bag to carry each day? Should a bag match or contrast with an outfit? What's a casual vs. dressy bag? Does size matter (HA!)? I know there's a secret world of purse knowledge out there!