On the run this morning, but here are my impressions:
Hurrah for the pink! It's a big yes
The buttons should go, with maybe burnished metallic or tortoishell in their place -- easy switch
Love the Annie Lennox vibe (shout out to Shevia). What about a v-neck tie blouse, with the tie end draped, not in a bow?
Or what about Bowie reinvents his school blazer? Or just embracing the prep by popping the collar and wearing a striped crew neck sweater, or a button down, underneath. When you go Prep, go BIG!
Take a hippie/arty tack: What about this over your flowy, architectural sleeveless dresses . The length of the jacket might be a bit long for this, but it might work with heeled booties.
What about mixing it with looser, wider leg pants? I could see it with a JCrew crew neck sweater, with the sweater and jacket sleeves layered and scrunched, jacket collar popped, flowy wide leg trousers and heeled booties or oxfords. The trousers would have to drape, though, to offset the structure, and the sweater would need to be relaxed through the torso. Think Kate style trousers (but I'm guessing these aren't already in your closet -- I do think Kate trousers and a t-neck would work for you, btw).