Zak: Before I was out as trans, I always wore clothing from the women’s section that looked like men’s clothing to formal events. My go-to outfit was a pair of black women’s slacks and a white button-down shirt. No one complained because I was technically wearing women’s clothing, and I felt more comfortable than I would have in a dress. Your family might still find your outfit unsuitable, it really depends on your family’s personal tastes, but it might be a good compromise for you. Slim and skinny cut men’s khakis are so in right now that you could probably even get away with wearing men’s pants if your family doesn’t police what you wear too much. Hope that helps.