Yeah, I've brought it up many times before. Pretty much hate the dad/business casual look of shirts tucked into jeans. Maybe it's the nice combo of shirt belt and jeans that he has going on that makes it work there, but I really like it tucked for some reason.
Shirt is too long to be untucked in that fit, that's why. If everything else was a little looser and slouchier (overused term sf13??) then that particular shirt would look good untucked there. Personally I don't like the tucked-into-dark-indigo-denim look, but yeah. Still looks pretty good though
Yeah, I'm sticking with it tucked in. I think the length of the blazer is also a factor. With a longer blazer, it's usually easier to get away with an untucked shirt (provided the pants + shoes match as well).
Can't tuck the blazer in—it has these sharp little teeth lining the inside. I haven't been able to separate the shirt and the blazer ever since I made the mistake putting them both on at the same time.