1. Slouchy and/or reservoir-tip beanies.
2. Thin, wispy scarves.
3. Pants tucked into your fucking boots.
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.