Probably my black caviar M/L SHW classic flap. It was my first one, which I thought was going to be my only one. I just feel like this size and color combination is the most versatile, and durable.
However, I haven't used a Reissue, which I plan on buying next (very soon!) I may change my mind at some point in my future.
I'm 5'2" for reference. Jumbo is/was out of the question for me.