[Jainarayan]

Shorts, loafers, no socks, untucked OCBD: okay then.

I like that look... shorts, loafers, no socks... but the shirt tucked in. For some reason I think it looks more put together. Of course that's just one more opinion on the topic.

I think this is sexy as hell; the beard and haircut are on-point too.

 

[Charles Dana]

I like that look... shorts, loafers, no socks... but the shirt tucked in. For some reason I think it looks more put together.

I agree. In the above instance, untucked is just okay, but tucked looks much better.

 

[triklops55]

I like this point, and I've noticed it. Here's (nothing more than) a personal anecdote:

I once saw a 30-something guy wearing an untucked ocbd shirt with jeans. To me, being a gay man and a fan of bears and bellies (he had longish hair neatly combed back, full beard, and a nice belly), I thought his belly would have been better served by tucking the shirt in. But the point is, as you said, some guys don't want to bring attention to their bellies. Ah, what a shame!

I have a belly and always tuck my long-sleeve shirts. To me, a guy with a belly and an untucked shirt looks too much like a pregnant woman. A tucked shirt, with well-fitting pants, gives a man who has some extra weight a waist.
To me, leaving shirts that are meant to be tucked untucked looks like the man is trying to hard to look cool and casual.

 

[16412]

I would say, doesn't know what cool is.

 

[eagle2250]

I have a belly and always tuck my long-sleeve shirts. To me, a guy with a belly and an untucked shirt looks too much like a pregnant woman. A tucked shirt, with well-fitting pants, gives a man who has some extra weight a waist.
To me, leaving shirts that are meant to be tucked untucked looks like the man is trying to hard to look cool and casual.

Or perhaps just trying (unsuccessfully) to hide the overhang!