It's a critical rule of thumb for me:
tuck the t-shirt or a-shirt (wife beater undershirt) into your briefs. Boxers ride up, so this rule of thumb just doesn't work well with boxers. But when it comes to dress clothes, wearing boxers doesn't make sense to me anyway.
So it's tuck the shirt into your briefs and then fold your dress shirt neatly over your underpants, pulling up your trousers and buckling your belt or snapping on the suspenders/braces over your shoulders.
I find it comfortable to tuck the whole thing (that is t-shirt and dress shirt into my underpants, but that often results in the lower part of your dress shirts getting very wrinkled by day's end. Nonetheless, if I know the shirt is going in the wash, then I usually will tuck my dress shirt in my underpants as well.
In response to another comment from one of the users of this site. Yes, there is the possibility of your trousers slipping down as you move in your seat, but then worse things have happened at sea. Real men don't comment when they see other men's shorts. This world could do with a lot less fussiness about such things. (I'm just glad a guy is wearing underwear, for god's sake).
Old School is the New School
