Deadly Cyclone
Pride of Iowa State
Yeah your shirt is gonna get cinched when you tuck it in but that's a fact of life. I would have to see how it looks on you to say for sure, but I would guess having your shirt tucked in all the way would still look better than tucking it in and then slightly pulling it out to cover your belt.
Maybe I can take a pic or two sometime. I've tried it and it looks bad with my clothes, I just assume they aren't fitted enough. My friend looks great doing it your way though. May be body type too, he's a bit more built in the upper body.
So what's the opinion on chinos + low cut shoes (Sperrys, etc) with low socks? Look fine? Do you need to roll up the chinos a bit?