I used to be all about jeans, a t-shirt, and Converse low tops for a while. If the weather got cold, I would trade the shoes for some boots and throw a hoodie or peacoat on. Even when I got my first black Utilikilt, I didn't wear it all the time, mainly just out with friends. Now that I have a kilt in a tartan, I am always wearing it when I am not at work, and sometimes there too. I still wear a t-shirt with it, but I make an effort to make sure it matches, or at least looks good. I still wear the low tops too (have an arch problem and my insoles fit them great.) If I am going to go out somewhere, I normally throw a nice, buttoned shirt on with the kilt and maybe some hose and flashes if I am feeling dashing.