Ask the MB: Sport Shirt Tuck-In Clarification
--Evan in Maine.
A: If you notice the Bravo toolbags, they're all wearing denim. Unless your shirt is specifically designed to be untucked, then tuck in, especially if you're in jeans.
As far as the dreaded "dad look" goes, this has more to do with the choice of denim and belt-mounted communication device than it does with tucking in your sport shirt.