Here's why I'm thinking it's not working, because the styling shot is weird but not awful--it could be used reasonably.
the styling shot is different from how you're doing in the following, important ways:
the pants in the styling shot are weirder, more (seemingly) haphazard on the boot shaft, not half-cuffed.
The predistressed denim might be OK if your shirt matched up w/ the vibe.
An outfit idea (not perfect, but a little more coherent):
those boots+jeans without cuffing (you can keep trying the bizarro half-on-half-off attempt), scoop-neck tee (a lazy answer but it's what I can come up with at short notice), weird blazer or cardigan (maybe that long cardigan that's all the rage these days)
what's the rest of that styling shot?
edit: oh. no thanks (Click to show)
As soon as I left home, I wished I'd thrown on a scoop under the shirt. Went home, threw one on, got a better angle. Improved at all? Definitely hear you on the weird blazer or cardigan look meshing better though.