Buying the right size: when oversized can swallow you. I love an oversized look. It is relaxed and effortless. But going too big can actually end up taking over, making you look like you’re drowning in your outfit. If a piece is made to look or function as an oversized piece, there is no need to go up a size. Rather, you should be able to order your typical size and it will look relaxed yet tailored.