Style Question | American Flag Pin; Flip Flops

Im not a presidential candidate, member of Congress, nor a right-wing TV pundit, but I'm a bit intrigued by this whole American-flag lapel-pin thing. Is there a cool (or right or wrong) way to wear one?

As someone who works in DC and the political field, I don't have an American-flag lapel pin and neither do a lot of my colleagues; I do have a support-our-troops magnet. I have a lot of those, actually. You tend to acquire tons of them when your country is at war and all. Anyways, the lapel pin: Living in DC, its not so much a cool-or-stylish thing as it is a work thing. Its a political land, members of Congress wear them to identify themselves as Congressmen while others wear them to decipher their political party or show patriotism. This doesn't mean I am not patriotic. It sort of means I don't wear pins. I thought it was smart of Obama to avoid the knee-jerk American flag that politicians, lobbyist, and chamber-of-commerce types often sport, and then I thought it was smart of him to pin it on to show he wasn't rigid. But is it cool? No. Unless your a member of Congress, it just proves that you take things too serious. Is it uncool? Not necessarily. I'd have to admit that a Confederate-flag lapel pin would be uncool, unless you dig slavery, but that just means your uncool. But me, I'm not wearing an American flag...one day at a time.

Is it ever appropriate to wear dress with shorts? What about oxfords and wingtips? Ive seen Michael Bastian do it.

Yes, you may wear dress shoes with shorts. You must have missed my reviews from all the fashion weeks for Spring 2010 because shorts and dress shoes ruled supreme. Plus you have to wear something instead of flip-flops, because despite popular belief, flip-flops are not shoes! And as far as I am concerned, if you're bold evough to wear gladiator sandles, you should be prepared to die for them.