Because you're an actor, the answer is simple: you concede whenever it's not true to your character. Even as an extra, an actor should take pride in the role he/she is portraying. So, put yourself in the mind of the director who is directing the scene and the person who chose the extras. When the director told the casting person, "Send me 'everyday' men 20-45 for a scene at an airport," knowing that a man in a skirt "causes a scene," it is most likely not what the director had in mind for an "everyday" male.
Your skirts are part of your brand, YOU the brand, and it may get to the point where you're known enough for a director to say, "Get me the guy who wears skirts." Until then, your style is not what they're casting, your ability to play a character that is "universal" in the scene is.
If I stuck to my style when I was speaking on stage, I'd be in Ugg boots and thermal underwear, but that's not the "Hollywood" image the people who are hiring me to speak want portrayed on their stage. So, I put on the 5 inch heels, wear the sexy dress and finish it off with sparkly jewelry and viola... they've got their Hollywood Career Coach (but don't for one second think my Uggs aren't waiting for me in the car).
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