Uh, have you followed any of the Republican debates lately? If Obama wore a pocket square, the whole lot of them would talk about nothing other than how said pocket square is a symbol of big government, illegal immigration and high taxes. In our current political climate (where no one wants to work together and everyone is worried about the next election from Day 1 in their current office) I would not expect any politician to stand out in terms of dress, for fear of it being used against him/her.
But he does stand out in terms of dress by forgoing the tie/jacket and it is being used against him I did not word my post carefully enough, however. What I meant to say was that I don't agree with the president of the United States being bullied for not buying his clothes where the average joe can't afford to. You're certainly right about why it is such.