I am figuring out my silhouettes for fall/winter to avoid wardrobe orphans. I've discovered that unless it has a certain shape (and fabric and color), it doesn't get worn! So, here's pretty much the shapes I'll be sporting:

Long over skinny:
The key (to me) here is gently fitted on top and very slim on bottom.
- Tunic-length (midthigh or longer) tops or sweaters with skinnies and boots (both short, worn under skinnies, and tall, worn over skinnies).
- Shirtdresses or very plain dresses with leggings and taller boots. Longer tunic sweater over as needed.
- When it's colder, a mid-thigh-length trench coat, and a scarf.

Ice cream cone:
I call it this not because of the shape, but because all the fancy swirls are on top and the bottom is always the support act. So that's:
- Hip-joint-length shirts (knit, woven, or cowly knits) with bootcuts or straight-cuts, boots, and belts.
- If it's a knit shirt, add a vneck cardigan sweater over as needed.
- If it's a LS tee, *always add* a vest or other layering piece.
- When it's colder, a shorter jacket and maybe a scarf.

Yup, that's pretty much it. If it doesn't fit into my formulas, it doesn't get worn. I'm pretty proud of myself for figuring this out!