I think a decent pair of wide calf fitting knee high boots is a good investment as it makes it easier to wear dresses. That instantly makes me feel smarter and more put together.
I've just bought some barrel jeans which I am pleased with (but they don't have a good reputation on MN). I think they work for my shape. I'm going to wear them with boat neck t shirts and merino sweaters.
I'm hunting for a good denim dress as I have lost weight and my old one no longer fits. I have found a nice denim maxi skirt though which may have to do.