I wear mine with jeans and a v-neck or hoodie. I don't ever wear vans. I guess I'm just a converse girl. I wear my regular converse with shorts some of the time but I NEVER wear my high tops with shorts. It looks weird on me. But I looooooove my converse. I wouldn't really wear them with a dress unless they looked really good with the dress. But I don't dress up much so when I do I go all out. But my everyday wear is decided by whether it's too cold to wear flip flops or if I don't have clean socks for my converse. Theyre easily my favorite shoes. I've had one pair since sixth grade and now I'm going into tenth and they still fit, although none of my other old shoes do. They are dirty and torn and trashed but I have been to hell and back in those shoes and wouldn't give them up for the world. I <3 my converse!