Very helpful thoughts, you all! I found the exact version of boot I have, but mine is chocolate brown. Also, I meant to write above that the dress is just above the knee on me.
Jenni, thanks so much for the visuals. I was trying to think if I have ever worn leggings with a dress and I guess the answer is yes, when the dress is on the short side. I like your cute layered look. By the way, have you ever tried wearing thigh-highs? The good quality ones stay up really well and can be much more comfortable than tights.
Brooklyn, thanks so much for sharing those great outfits. I agree your boots work beautifully, but they are also a little more elegant than mine (see updated photo). I am putting brown tights and fishnets on my shopping list right now! I knew I needed new brown tights (thanks for reminding me), but I never would have guessed how great the fishnets work.
Sal, I think you are seeing what I am seeing, which is that the style of my boots and the style of my dress are just not talking to each other. I feel like the dress is asking for something sleeker. Good point about the ankle boots. I could try that too. I find ankle boots keep the foot a bit warmer than a pump. I would love a good mod boot should the right one come my way.
I am feeling brave enough now to start trying things on, but honestly it will be awhile before I get the free time to do that and take photos. So grateful for this help.