uh....there's a lot of questions there.....initially I would have said chocolate box 28, but if it's your first, you may not likt the scratches you get with box, so I'd go with the evergrain 32. The orange and blue jean are completely different choices to the first two you mentioned, you would have to take into consideration when you will be adding the next bag, and what type of wear do yo want out of the first one? The coloured ones can be more casual, and you need to think about sellier or retourne as well! LOL!