The "too cool" ones definitely need to get over it. If they are that cool, they can carry my laptop (which is one of the heavier models, one of my books out of several assigned for class that are at least the size of the largest dictionary you have seen, my notes, the supplements, any regular stuff I might take that day, and so on, and so forth...........They can carry it for me every day and then complain to me how other people with rolly bags "look." I got over worrying about what anyone thinks a long time ago. Do what feels comfortable for you and what will not give you a back injury down the road.