What to wear: Both the Winchesters are almost always in jeans and boots. Sam often goes for plaid shirts, while Dean picks solid-colored earth tones. Layer with black or green army jackets. Denim jackets work too! You can even make your own demon blades if you're so inclined.
How to act: Like you're on the hunt. Sam is usually more cautious and more of a planner. Dean acts now and thinks later.