Umm, spanner ahead...
First, know that I'm more or less positive that Angie would rather see you in longer shorts. I don't wish to speak on her behalf, but since she is not here and I have heard her express this opinion before (and I'm sure you value her opinion otherwise you wouldn't be here), I feel like I should just get that out in the open.
My own personal feelings are slightly different from Angie's. I do think short shorts can work, but I personally find this whole look to be too casual. It looks very much like a typical summer outfit for a lot of teens and college students in the neighborhood I live in, which even gives me pause and I am 27. I don't necessarily think you need to cover more skin as you get older, or dress more seriously, but I agree with Angie that the level of polish should increase, and this look just isn't polished enough. Dark denim shorts, a blouse, and nice shoes (not necessarily heels--metallic flat sandals would work just as well) would be more successful.
As I said, though, this is just what it would take to pass my filter. Angie would go further and let that inseam down more.
