I am on the verge of getting the black Chanel reissue in medium. I think it is a good size for transitioning between day to night. Also, the design of the bag seems to ask to be smaller, and not bigger, it wants to be petite and delicate. However I am willing to hear opinions on this. Perhaps some of you have it or the large and can tell me what fits inside... etc. Also, I am on the hunt for the gray color. If anyone has had any sightings.... Much love to all you bloggers!