Amy!!! I said this will be one style journey to follow and was I right or what!
And you sew...!!! This is wonderful collection of jackets. Did you make them all??
(Please excuse so many exclamation marks.)
D1: I remember the outfit from the skinnies post and love it as much as then. I wish I could see the jacket a bit better, I'm guessing it has nehru-collar and belt.
D2: Love it, even more because this is what it looks like when done right - I tried the same combination with my patterned dress and black blazer and failed miserably. My elements were not right together, but yours is great.
D3: Fun and I'd probably only change hose for something a bit more sheer. Super cute booties.
D4: This works for me. I think the boxy structure of the jacket balances the skirt nicely.
D5: Ok, at this point my mouth is wide open - if you've made this jacket then I have pretty good idea what kind level your sewing skills are! I love the original outfit btw, although I can see why it may not appeal to you too much (especially id you're still concerned about feeling exposed in skinnies). But, the white stitching of the jacket breaks the overall blackness of jacket + skinnies and the silky scarf juxtaposed against it all adds a lovely feminine finishing touch.
Cardigan is a great option too.
Last but not least, I like both hairstyles but the second one makes you look like Annette Benning even more.
Sorry to hear about the job, was it unexpected? (Sorry, no chioccie in the house at the moment.)