The only thing I don't like about suits is dry cleaning costs. Oh, and that with my body it's hard to find reasonably-priced dress shirts that are not too loose around the body but are fit my neck right to wear a tie.
Your comment implies he has been conscious, on some level, of how ill-fitting his clothes are. I don't think so - I think he just doesn't know or thinks they fit right. Edited to add: I meant ill-fitting his suits are. I can't comment about this shirts. Also, this thread is not political.
Those are their traditional fit shirts, which are quite blousy and loose. I know you're getting them tailored, but there'd be less tailoring if you got their trim fit. Also, if you're not going to wear a tie you can size down in LE shirts to get a tighter fit. I've got some 15x33 LE trim fit that fit similar to 15.5x33 Brooks Bros ESF.
You think most American men have a suit as "good" (and I use that tern loosely) as Paul Ryan's? They certainly don't have clothes as nice as what Obama or either of the Bush's wore on the campaign trail.