1. Provided they aren't neon or covered in obnoxious graphics, hoodies aren't bad. I wouldn't wear them day-to-day, but they're nice when you're just hanging out.
2. Skinny-fit shorts look fucking dumb. If you want to look nice, wear pants.
3. Bootcut jeans aren't that bad, as long as they're slim-cut and, you know, worn with boots.