Strapless with Shirt: Does the Look Hold Up?

I've been obsessing for the past few days about strapless dresses worn over shirts, especially since I misplaced the magazine where I recently saw an image that inspired me. (It was buried under a pile of novels. Imagine.)

While I was searching for the magazine, I tried out a couple of looks to see if I could extend the life of my strapless dresses into the fall and into the classroom.

One combination was a crisp blue gingham shirt with a cream dress heavily embroidered with blue filigree. I felt like I should be holding some chilled mugs of St. Pauli Girl.  So no it was to Oktoberfest.

Another combination was a bright watercolour-y floral silk dress over a Liberty of London pink rosebud-print shirt.  It was bold and wild, but not in a gorgeous Issie/Daphne manner.

But the above look (east corner) seems "just right" to me.  Lovely menswear checks with a feminine silhouette.  Would gentle readers give this--or somesuch version--a try on?