I've been dressing myself as a pear rather than hourglass forever, so this is a step way out for me. I ordered a long, which is translating to a midi, but it is loose enough at the top that it doesn't sit at my natural waist, but a couple inches below - so if I have that nipped in it should be less midi. I plan to wear it with dressy black boots this winter (that I need to buy). I have it on with a tank to show the silhouette - and I threw on my silk shirt as a styling idea that certainly needs some tweaking. Theoretically as an hourglass a pencil should work but I feel shy about it. If the idea is fine, but I should keep looking, let me know that too.