Oooo! I want those earrings!

Must say, you seem like the definition of Soft Gamine to me! Thus anything too square-edged will probably always feel a bit off to you. Imagine keeping the jeans (slight hem roll, definitely, because that creates a little curve) but replacing the boy shirt with a silky blouse in a pretty color with a gentle collar. Meanwhile, maybe tweak the shirt a little by rolling the sleeves above the elbow, then pulling the sleeve fabric out above the roll into a slight puff? Anywhere you can change a straight line into a curve should work for you, I think.

Thanks Tulle. I can see the look before my inner eye! I should think about a way to test drive it...

I wonder if this is missing the feminine touch you mentioned wanting in one of your WIWs?

Thanks Eva! Yes I think that might be it, whatever you want to call it.