1. A sweatshirt should never be worn in the summer. Whenever someone is wearing a large black hoodie in the summer people are automatically going to judge you. They will that you are fat or that you are hiding something under that hoodie and if you are visibly overweight even with the hoodie on then there is no reason to wear it, right? You might as well get a lonehood from styleuno.com if you really want to wear the hood and you can wear it with any clothing. Because there is no need to have a full sweatshirt in the summer. P.S. There is a reason why "hoodie season" and "hoodie weather" are such well-known terms.
2. Sandals. I don't care if you're trying to be like Mark Zuckerberg in the Social Network, you should never wear sandals in the fall or winter. Your feet are unprotected and it just looks ridiculous. Especially if they are open-toe sandals, which just about all are now, because your feet will freeze off and we know that sandals with socks is forbidden.
3. Sports jerseys. If you're going to wear jerseys at least wear them when that sport is in season. We all know that jerseys are no longer the great fashion statement that they used to be. They used to be acceptable in all scenarios and circumstances but jerseys are no longer at that level. If you are going to wear them today, don't wear a Tom Brady jersey in the middle of the summer. Safe if for the fall, it only makes it that much more special.