When a person is looking very fine, specifically because they have the latest trim(haircut) and/or are wearing the latest fashion.
Girl 1: "Damn, you see that boy the other day? He was looking crazy fresh!"
Girl 2: "He always looks crazy fresh to me!"
Boy 1: "Guuurrrllll! You looking crazy fresh with that new trim!"
Girl 3: "Thank you."
Boy 1: "Any chance you'd want to get coffee or go to a movie?"
Girl 3: "Sure."