I love this slouchy, knitted hobo from Urban Outfitters. It's massive and cosy-looking and I think I'd feel all effortlessly cool when carrying it (well, you know, as effortlessly cool as you can be when you only ever go to pick up your kid from school... and the post office), but with the pretty much constant rain we've been having, I don't see this bag as a practical option. Particularly since it's dry clean only.
Exclusive to Urban Outfitters, it costs $68. Ah well, maybe for spring, eh?
Related: Plaid cosmetic case from Urban Outfitters | The 'Fake-a-Gamo' knitted handbag | Free People's crochet patchwork satchel