In this case, I brought in dark wine colored tights, to bring out the burgundy and fight the purple hue it tends to suggest. I also work it with my nerdy oxford flats. Then I felt I had to bring in some black, to balance the black shoes, and in came the black shirt and blazer (it was cold, but I didn't want more gray in the form of my gray cardigan!).
I hesitated on posting this Outfit of the Day, but this blog is about Developing Style--not showing style I already have, not just documenting successes, but a record of how I change and evolve.
All in all, I think this outfit doesn't work very well. I also get this problem with my orange wool skirt--so hard to style! Length is slightly too long, cut is slightly too boxy--but I love it so, and am convinced it is vintage from the 1940s (metal zipper, wool fabric, slim A-line skirt, hand sewing techniques) so I don't want to give up. Any suggestions, or should I just admit defeat and toss them? Have you had any cases when have an item that theoretically should work great, but in reality it just never quite clicks?

Shirt: Gap via Plato's
Blazer: H&M
Skirt: Zooc via Garage Sale
Tights: Hue via Plato's
Shoes: Naturalizer via Goodwill