You might be right about the collar. In the first photo above, I can't tell if the jacket collar is a bit loose or if it's just the general badness of a point shirt collar.
But the second photo illustrates why very very few people qualify to wear a paddock. The gut-emphasizing qualities of the bottoned lower button mean that only men like David can wear one. He looked okay because the guy, like you I believe, weighed about 95 lbs soaking wet.
Agreed, but I've a general prejudice against point collars. Do you've the same opinion about double breasted coats?
Perhaps you did not mean to, but you touched a point related to Politics, so I presented one of the most basic authors so that you could educate yourself with a different and very well regarded point of view.
Nice outfit! The square is match-y, but you know this. Btw, is it really black and white or is the photograph off?