Originally Posted by The Louche
This depends if you can carry it off. Sinatra, for example, was seen frequently with his collar un-done. He looked rakish this way. Most, however, look like idiots or slobs. I'd err on the side of safety if I were you. You, unfortunately, are not Sinatra my friend...
I see many office workers and classmates try to pull this look off, but many times they just look like slobs. The only time I really see this working is Happy Hour.