1. Slouchy and/or reservoir-tip beanies.
2. Thin, wispy scarves.
4. Fucking jogger pants.
5. "Crutched" fucking jeans.
6. Pants cropped up on your fucking calf, fuck.
7. Shoes without socks in winter.
9. A Mad Men costume, basically.
10. Boat shoes in place of loafers.
They're not the same thing, and they can't be worn in the same way.
Why don't you just: Get some actual loafers and save the boat shoes for your actual boat.