To Tuck, or Not to Tuck... That is the Question

 I recently bought the J. Crew navy check shirt - and I absolutely love it.  My dilemma today is about how to wear this type of shirt - the casual, relaxed-fit, button-down shirt, with a shirt-tail hem.

As you can see here, the model has the shirt untucked completely, which looks great on her, although can sometimes look sloppy, but is generally my "tuck" of choice.  This outfit, along with a black Jackie cardigan, is how I wore the shirt last Friday.

Overall look = B+

Another option for the button-down shirt-tail is to tuck it completely in.

Overall look = C+

Tucked in, the overall effect is much less casual, and depending on the pattern, could tend to be a more formal look.  The tucked-in shirt can work well for jeans or looser-fitting chinos or cords, but when I tried this with skinny jeans or Minnie pants, the bunched-up shirt was visible through the pants (a la VPL/visible panty lines).  Definitely not the look I want!

Now check this out:

Overall look = A

The model here has the shirt half-tucked in, half-out.  I love this look.  I saw this photo and have been able to re-create it nearly to perfection.  However, whenever I try to pull it off, I feel like it is obvious that I did this on purpose.  It looks staged, overly trendy, and like I'm "trying way too hard."  Again, not the look I'm going for.

Has anyone been able to pull off the "half-tuck" and make it work?  Any tips on making it look less planned and more like a happy accident?  "Ooh, is that my shirt-tail coming out? Gee whiz, I didn't even notice."