I have both and the Monty PM is very comfortable, but I wore my Speedy today, and it is more classic and beautiful IMO. I, too, have the "grass is greener" thing going on and still always go back to my Speedy. For fall, they are showing the Speedy with a strap and several people have told me (in another brand boutique) that the strap is the latest accessory! I would invest in the strap for the Speedy (I use mine occasionally) to use when you need a shoulder bag. I know not everyone likes the look, but I remember the days when that's the way they were worn, and I think it looks great either way. The SA told me that you just let the strap dangle from the bag when hand-held - that that's the new look!