Isaac: First, you don't look "googly-eyed". Your expression is direct, even matter-of-fact. That's a good thing. Your mouth is a bit grim - almost as if you're about to say something unpleasant, or at least unwelcome.
As for your glengarry, it looks fine. Whether you wear it, or not, with "civvie wear" is entirely up to you. Some folks, like me, will think it looks great. Others will think, as you have already read, that it would be more appropriate with a uniform. The vast majority will just think it is some kind of Scottish hat, that they have seen before, or some other foreign head covering. If you like the look, by all means wear it, ... and post the pics. 
John
I changed my signature. The old one was too ridiculous.
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