Here is the thing about the DR, but really this applies to any piece of, what I will call, "more eccentric" article of clothing. Some people are just born with the look, personality, or swagger to more easily pull off anything they put on, initially anyhow. That said, when someone gets a new, notable item of clothing or tries out a new look, it is unusual, because it is new. It is not something your friends, coworkers, or family currently see as "you". Hence, you get more comments, be them positive or negative. After awhile, if you stick with it, that new look becomes "you". It has been associated with you long enough that it no longer looks out of place and it is no longer a question of "pulling it off". That is simply how you dress.
This is why celebrities get away with their more outlandish style choices:
They are already associated with an image. Whether you like their style or not, you aren't surprised when you see it.
I guess I will put it this way. If you like it and can feel comfortable in it, you will eventually "pull it off". The question is then: what jacket/style do you like best? Or what style/jacket do you want to become your style?