I read Angie's blog post today with curiosity to see some new stylings. The vast majority of my dresses (all but two) are summer dresses and sleeveless, so it's unlikely I'd layer them over pants because I wear them in hot weather.

However, I do have a sleeved dress from nearly 10 years ago that has managed to survive many closet edits -- it's a bold black and white check pattern wrap dress in a crisp cotton, and being a wrap there's a little play in the fit, so it still works for me now that I'm a size larger than when I bought it. I've worn it over leggings in the past, to help ease the comfort level of a wrap dress that doesn't provide a ton of coverage when I sit, but I no longer wear leggings.

I pulled it out of the closet recently to try on, and out of curiosity I tried it over my black wide-leg pants from Athleta. Surprisingly it seemed to work pretty well, so I may try wearing it out soon.

Finds show the items, but my pants are black, not navy. 

If I could ever find a shirtdress that worked for me, I'd enjoy trying it duster style over pants, but that's a tall order.