So..This is a casual look, something I love doing. If you live in a cold place, like me, you can wear tights under the shorts. If you want wear a bigger jumper for more of a layed-back effect um DO IT. I love the boots as well they just make the outfit. The bag I tried to keep the same color as the sweater to keep it basic and so there wasn't too many colors. I love Taylor Swift so chose her, I think she would suit this look.
This was just random but I wanted to stick with the bright colors of the american flag, red and dark blue look so nice together! Then I add the converse for simplicity and because there an american shoe (sticking to american theme) Hope you like it.