They are comparable to Chucks, prob a little more comfortable than that. I can't wear Chuck Taylors, they just kill my feet. I love Vans and I have been wearing them for 30 years. They do make Hi-top vans, which I like, if you need ankle support. Also sometimes you can find ultracush Vans. The Ultracush Vans have a lot of padding so they are very comfortable. I walk a couple miles from the train to work and back every day so if I were to wear Vans all the time my feet would hurt. But for a few days in a row here and there, and normal wear on the weekends they are totally fine. I don't need orthopedic nurse shoes every minute, I'm not that bad! you could always toss in a pair of Dr. Scholls gel inserts if you were really worried about it....