There are a great many threads on the ability of cross dressers to pass as actual women and after making some assumptions as to why I do not pass I did a simple search and found that perhaps my assumptions as to "why" were wrong.
Now, I have long posted that there are a million subtle cues that give away the male dressed as a woman, EVEN IF your attire and gait are flawless. My assumption was that I can hide my body under the right clothing but my jaw line and chin are the give aways that i can't hide or blend away with makeup. So the search I did was "square jawed women." Many beautiful women popped up and they all had square jaws but you'd never, never mistake them for a man. An example is attached.
Now, rather than the jaw line, take notice of the neck in relation to the jaw. Her neck, and all examples I found (100%), clearly starts inside of her jaw outline. To me this was a "eureka!" moment. Most, not all, male examples have necks that align with the jaw outline. Mine does. Now, add in the shape of the trapezius muscle as it runs in to your shoulder, and you get a very distinctive "male shape." From a "head shot" perspective only, this is THE distinctive tell.
So, what's the take away? 1) don't worry about a square jaw or chin. 2) if you want to blend, work on disguising the neck/trapezius (my wife suggested trying scarfs), and 3) get real about our physiology. I do not "pass" but maybe I can confuse. Regardless, you can go out and still have fun.