While I’ve Always Been A Fan Of Button-down Oxford Shirts In A Casual Setting, I Prefer The Clean Line Of A Straight Point Collar. But Whenever I Wear Point Collar Shirts Casually (top Two Buttons Open), The Collar Will Open Up Leaving Me Looking Somewhere Between Saturday Night Fever And Hungover. Should I Just Suck It Up And Stick With Button-downs?

This is what button-downs are for, frankly.  I’m not saying it’s your only option, but the button-down collar was created to deal with this problem. 

You can certainly unbutton only the top button on a point collar (nothing wrong with that).  And for shirts with stays, you can try using those super-magnets that hold your points up, if you like.  I’ve never used them, but I’ve heard they mostly work.