On the lighter side: in my opinion the redder the better with lipstick, clothes and wine.
On a more serious note there is nothing wrong with being transgender. Don’t think you’re less deserving of something simply because you are trans. Your journey is your own, so live it, and decide who you want to tell and when/how. In my experience, however, the earlier the better.
It may be scary but at least it’s authentic. And an authentic life is worth the struggle.