So I'm 30, married presenting as neutral in most cases but slightly maleish. I do dress up completely as female as you may have seen in my post history. My wife of 2 years (been together for 5) decided to tell her family early on and they've been pretty cool with it. I wear jeggings around them, women's skinny jeans, nail polish too. Well I'm over there house with my wife with black leggings, a football Jersey and women's knee high boots. My sister in laws BF always notices my outfits after like 4 hours together, but anyway that's side.
I'm helping my FIL take out the trash and some kids walk by and a girl turns around and says, "are you wearing leggings?" I said yes and they have pockets! My FIL turns around to them and say, "You like em?" And they just turned around and walked away. He's always been okay with me but I've always had to run things by my MIL because sometimes he's not always 100% comfortable when I add new things to my wardrobe.
But a biG shout out to my FIL for having my back!!!