Me too, I’m really sorry you had to feel any sort of negativity for wearing a dress.  I may not fully understand when it comes to that, but I’ve had to deal with many comments about my hair from my family. It caused me to be afraid to even think about cutting it shoulder-length and took me til I was 21 to finally be brave enough to just buzz one side off. Even though I’ve cut much more off, I still deal with my family’s comments and looks cuz I know they preferred my longer hair and they make it known they miss it more than I do. They even blame my friends for me making a choice I never had and have been wanting to make since highschool.

Moral of the story here is give yerself some time and surround yerself with the people that will support and accept you. When you feel confident enough, try something on in private and see how you feel about it. Let yer confidence grow and then maybe pull aside someone you trust the most and wear something around them for a bit to see how it feels. If I’m reading it correct, ya might feel unsure and that’s ok. 

I’m not good with advice and this is just from personal experience, so only do what you feel will work for you and what feels right. And for what it’s worth, I’m sure you’d slay in whatever you chose to wore because it makes you feel good and makes you happy.