And yes, I plan to have Lily in both wardrobes depicted, depending on the weather. I kept the striped dress I had her in last time, but decided to put her in something more stylish for Fall/Winter wear, so I went with a sort-of 1980s look! I added glasses to one of the Lilys as a test, to see how she would look with glasses on (something else I played with from time to time). I did the figure on tablet in Photoshop. I simply had two sets of clothes/accessories that I could easily toggle, and pasted two types of figures onto this comparison picture.
This is very close to what I want for the final design. As a matter of fact, my earliest drawings of Lily used a style very similar to this! :)