Kelly, Suz, and Angie wear this look well!
I tried and it doesn't work for me, but my body type is very different from theirs. With a skirt or dress, I need the ankle to show, or to be fitted with a bit of a heel, such as in a fitted bootie. I can do low-top sneakers with a skirt if I style the outfit carefully, but even that's not my favorite look on me. I stick with wearing my high-tops with cuffed/rolled jeans.