It sounds like you have your decision sorted out, but I just want to send good vibes to you as you deal with the situation with your mom. I know how scary and stressful it can be. Hugs!

I think the dark brown ones are the most universal. In case you're in doubt whether it will go well with the dress I can recommend jointrendy.online - it's an extension where you can upload a picture of you in the dress and then virtually try on the shoes and see whether they look good together. It's in beta still but I got lucky to get in, and may I tell you - it is something!

I'm very late here but wanted to chime in: I am so sorry to hear about your parents--what a difficult, stressful situation, for them and for you!

Re. the boots, I'm going to be a spanner (as Angie would say :): I would go with your first instinct and get the chocolate brown! I think they would be splendid with your black print dresses and all of your gorgeous denim. Not sure why, but the mushroom doesn't seem like you, for some reason (can't quite articulate why). I do love the black boots on you too, I think because the bookending with your hair is so effective and visually cohesive.

Olive and chocolate are my votes.

Thank you all for your replies! It's so helpful and a nice break from the mundane!
@Jonesy: That's interesting! I was wondering if dark brown could work as a neutral or not. I just really wanted to get away from black and was afraid that it was too much the same. I'm going to ponder this some more!

I hope you’re maintaining your equilibrium. IMHO espresso/chocolate brown bookends your hair better than black and provides more energy. Maybe your eye color? I love, love, love that color on you.

I think both chocolate & mushroom work, but for different reasons. Why not get both? Haha jk!

Mushroom does work as low contrast over your bare legs. But I could see the dark brown working over tights & other looks too (like jeans) - like Donna says, it bookends too.

PS - I'm sorry about the parental situation. It's difficult to know what to do but at this stage I'm sure they appreciate you being a sounding board for their pain, even if you can't outright fix their medical issues.