In the area I live, anything except a decent-sized messenger bag, backpack for school or briefcase would be misunderstood. But, then again, I live in a rural, backwards area, too, and many of the stereotypes and attitudes here I find repellant. My dh carries a messenger because he needs to carry his laptop with him almost all the time, but he would never carry a smaller bag. As far as I am concerned, attitudes will never change unless people do what feels right for them, so don't worry about the attitudes of small-minded people. If you love the bag you are carrying and find it useful, then it is more than acceptable.