I'm trying to come up with some ideas for DH for Christmas. Ideas for gifts for ME that is. I really like the look of the Hamptons medium carryall. I am an hour away from the closes store, though. Without being able to try on a bag, it is hard to tell how it will feel on the shoulder. Is this bag okay for a shoulder bag or is it only a handbag? My second choice would be the newer style Chelsea medium hobo. Since I like a bag that can be either a handbag or a shoulder bag, which would be better? For reference, my two fave bags right now are my black signature legacy slim flap and my chocolate signature medium soho hobo. That is about the size/feel I like best.