Although it's not my favourite bag my second-hand (through Annsfabulouscloseouts) red small Marc Jacobs multipocket is the most comfy bag to use- the outside pockets are just sooooo easy to use and give me direct acces to my phone, keys and public transport pass without opening my bag. The only problem with it is that it is a bit small, so I guess I'll have to buy the large MP some day to have an even better bag.
YSL downtown rainbow - no worries about dirt, with brown leather with metal studs at the bottom, open wide, accessible, can carry a ton, yet looks sleek and pretty
I also have to say that my LV Speedy is the most comfy bag! It's soooo light wight & sometimes can barely even feel it on my arm! (I don't overstuff my bags as I hate to carry a ton of stuff)!
A tie between Le Pliage Cuir Medium, LP Neo Small and Mulberry Flight. All are lightweight, roomy and I can carry them crossbody. I used to have a perfect, comfy hobo but my bunny ate the shoulder strap so that was that for that...