Personally I would get the black caviar jumbo over the boy and as some of the others mentioned, a reissue (226 size?) could be a good choice too!
My advice is get the black jumbo. I have both beige claire and black jumbos and to me black is alittle easier to carry casually. Also, intially I didn't like the boy bag but when it was made with the perfect color and hardware that I loved I had to have it. Let us know what you decide