I think the bit about makeup applies to all of us-there are certain things that people look for when they're "trans-spotting", and the stereotypical "drag queen" look is one of them. Warm-toned lipsticks, overly large lashes, and smokey eye looks give us a way in an instant. Cool toned (pink, burgandy, and purple) lipsticks, matte foundation with only basic highlighting, and natural eye looks generally give you a huge edge when it comes to passing. Here's the key: People are not expecting to see an transgender person, so if passing is your main goal, you need to defy those expectations. Which is why I wear purple lipstick every day.
Hair sucks. Mine especially! I will never be able to have long, feminine hair-it's a vastly overrated thing, long hair, but still...I'm not doing my bone structure any favors with this style.