Hmm... I would most like wear a pair of black trousers and an off-the shoulder top silk top that I'm having made. Or my leather skirt (which has a long slit at the front) with a pale blue sleeveless silk top with this bold embroidery around the neckline.
My suede high-heeled pumps would probably go with both outfits. And make-up, of course. I rarely put on eye makeup so that would also have an effect. If it's an important function, I'd have the hair stylist, who is also a make-up artist, do my face and hair.