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The size really depends on what you are planning to use it for and how much you carry around with you? My first was a medium flap as I felt the jumbo looked too big on me. Now I have a jumbo and love it because it holds so much more!!!!
As for the colour, black is always classic but red is hard to find. So these two get my vote.
Let us know what you get!!!
Have you tried them on for size?
For a classic bag the jumbo was too big for me. The medium was perfect and looked more "classic" compared to the jumbo.
My dream bag is the jumbo red in lambskin.
My classic bag is black med cav with g/h (I've always thought g/h to be classier.)