It's not a look I like for myself, but I don't mind it on others. Skaters I've seen in shorts generally wear the same tanks or t-shirts they wear over leggings.
Not my style i'm afraid. I've always favoured keeping muscles warm during training with long leg leggings and several pais of tights with optional leg warmers. Only takes for you to stop for a few minutes to take a drink and then push off again against the cold air for a muscle to pull or worse. So i've never been into the shorts-with-thights-to-the-air look. I think on the top you would wear pretty musch the same things as usual.