My existing non-gear handbag collection is:

Small black purse with silver clasps. It's awkward to use and doesn't hold much.

Gold Madison Sabrina: I regret this purchase because the duffel shape just doesn't work for me. Since the zipper doesn't leave the whole top open, I have to root around to find anything and it's so big, things don't even stay in the same place I left them.
http://www.amazon.com/Madison-.....B00460166W

I think the key for me is to use bags that are flattish and rectangular so I can pack things within them. Also, for anything not tiny, I need a passport-size zip pocket and inside pockets for cell phone/ipod as well as a zip top for security.

Bags under consideration:

1) RULED OUT: Smallest shoulder bag to hold keys, wallet, cell phone and 2 out of ipod/camera/sunglasses. Would this KS bag (black with white detailing) fall under euro-chic? Also, is a 14" drop length too awkward? I guess it can't be worn cross shoulder. No returns if I choose to order this one.

http://www.katespade.com/desig....._color=274

2) Small shoulder bag that can hold keys, wallet, cell phone, ipod, camera and sunglasses. Maybe I can stuff a scarf and gloves on top if I need to. I found a white Kristen hippie on deep sale, which should be arriving soon. I suppose white makes it a summer only purse and I'd need a small winter purse as well?

http://shop.nordstrom.com/s/co.....ie/3159279

3) Medium shoulder bag that can hold all items from first two purses, plus at least two out of (water bottle, small knitting project, scarf/gloves, superthin cardigan). I have a 10X11X3 gear bag which fits this description already but I want something that won't look out of place in Montreal/New York/London/Paris.

I sort of love the green and plum versions of this, although they would require some sale stalking. They feel a little too staid for euro-chic but they are really functional...

http://shop.nordstrom.com/s/co.....bo/3159227

(Side note: I had a "medium brand" purse that broke in less than a year. I really need something that can handle everyday use for at least 2 years)