Thanks for the comments guys. As far as the jacket goes, I see where you're coming from, and I myself was wondering about buttoning it, but I like the very trim, hardcore waist suppression, English military feel.
I wore the undershirt because it was a bit chilly/windy. Do you think something navy, perhaps a v-neck, would be better?
Finally, I didn't tuck the jacket because that always feels odd to me with the low-rise NSs, and it seems to cause this weird billow right abouve the jeans. Maybe it's just me.
The boots are indeed Ropers. I love 'em. And gza, a bag would've been a good idea on that trip-lugging college viewbooks and catalogues around NYC and Boston was a bit of a bitch.