A Leather Jacket

As soon as a man is about the size he’s going to be as an adult, I recommend picking up a nice, Made in USA leather moto jacket, especially in brown.

The style with the short standing collars has been in for about 60 years, and I think it’ll be a classic look for another century, given how slow men’s style changes. Get the nicest one you can afford and learn how to take care of it: whoever you pass it down to in your old age will thank you.