"They look like the late Tony Randall, natty but distinctly of another time."  -- That would be men who -- gasp! -- tuck in their shirts these days, when the hipster tide has turned to the Untucked Look.  As a lifelong devotee, I can only say its time has finally come.  Tucking in my shirt gives me flashbacks of childhood snowsuits, turtlenecks, and scratchy dresses, outfits it was impossible to escape from easily.  I think the rule is a little different for women, anyway -- men who tuck in look neat, conservative, maybe a little uptight; when women tuck, there's a "prison matron" thing that happens...or a "1970's secretary" thing.  No thanks.