I have traveled with 2 small rolling (carry-ons) The reason for two is that when I took a back pack etc, it was so heavy when filled. So what ever was in the backpack I just put into and carry-on rolling case. I used the smallest on I could find that fit my stuff. I did not want to carry the bag, rolling was easier.
As for the one with the clothing, I got clothing that was light weight and folded flat. I was surprised in what I could fit into the case. Even the room steward said to me when he saw my closet, "you fit all that in the one case". This was no princess where the walk in closet is open, no doors.