Do you mean, or as a dress up costume, or on a daily basis? If as a dress up costume, definitely yes. On a daily basis, if this is the style that you like and is you, then why not? Who cares what anyone else thinks!
Sure, but why would you want to?
Only if you're planning to travel to 1985.
Other people asked questions on similar topics, check out the answers they received:
Other people asked questions on various topics, and are still waiting for answer. Would be great if you can take a sec and answer them