Not arguing for/against masks, merely pointing out the analogy. For your parachute analogy. Imagine that its given the parachute will have very large holes (similar to the droplets being very very small). Its useless having a parchute in that case.
I get your argument but unlike a man crashing to death, we are playing a probability game here. Viral load also matters, even if you can stop some of the virus from entering, it can only help.