I'm putting together an outfit for a special "date night" out at the theater in our nearest major city with my spouse to celebrate finishing a round of treatment for a serious illness. While first drawn to traditional party dresses, I knew that I wanted to avoid unused party wear sitting in my closet (I wear business clothes during the week and jeans/sweats on weekends/evenings in my very casual community, and we have no formal party occasions to go to). So, I looked for things I could wear again or that were already in my wardrobe. Also, we like to walk around and check out holiday decorations, and I don't want to be cold or have sore feet on our special night--temps will likely be around 25 degrees Fahrenheit.

So, below is a collection of what I'm thinking about wearing. There are two shoes posted: I realize these are not fancy shoe choices but I could not find festive, warm, comfortable shoes, and I hoped to find footwear I could wear again. Thoughts about either footwear choice?

I did find a dress alternative (red lace shift) that I'm also posting for your feedback in case the black dress does not seem dressy enough. It's nowhere near as warm as the black wool dress and I've struggled to find comfortable, low-heel winter shoes that would work with it, but I'm thinking about keeping it for warmer weather and dressing it down with a denim jacket in spring and fall for less formal dining out. I have virtually no dresses and have a hard time finding dresses that don't feel constricting around the waist...and I love red and lace! As you can probably tell, I'm a big fan of 3/4 sleeves since they don't require alteration on my short arms. I'm 5'3", so the red dress hits me at the top of the knee (longer than the model).

This is my first YLF post and I greatly appreciate your feedback!