The first server was a very effeminate "out" cis gay guy from an era when gay men did not have as much acceptance as they do today, He didn't care (which was cool by me) but on Halloween he came to work as a drag queen - complete with heels. First of all, the company costume rules forbid any potentially dangerous footwear. Heels definitely fit that description but- when the store manager (a genetic) called him on it, he said "why? you wear heels in here all the time?" I bit my lip and vacated the area and the next time I saw him, indeed he was wearing his pumps. The "moral to the story"? His feet were killing him after his four hour shift. He had won the fashion battle, but lost the war!
The second story comes much later in another restaurant and really came out of no where. I had one very androgynous server on my staff and really gave it no thought how he would dress for the Halloween shift and in fact, didn't even though he was scheduled. I (like everyone else) was surprised when he came in to work cross dressed and I didn't even know him. My only real tip off came when before he came back to clock in for his shift, he stopped at the bar and said good by to his girl friend who had brought him to work. His costume for the shift was simply coming as one of my genetic servers and he effortlessly succeeded.
I can't even begin to tell you how many of my regular guests that night asked me who "she" was and was it true "she wasn't?"
Those two experiences were about it over the years. Not many "braved the restaurant" elements to cross dress or do drag at Halloween in any of the restaurants I managed. Over all, it was just too tough to do because of safety considerations. As far as I was concerned, I never even considered coming to work as a girl at all. In fact, one year I came dressed in my old Army uniform (yep-still could fit in to it in the mid 1990's) and one year as "God". I wore white sheets over my regular dress shirt and tie. Wore one of my huge "mistake wigs" - a long straight platinum blond and cut off enough to make my self a "Fu-manchu" mustache.
Think of it this way, if God says did you enjoy your meal- you dammed straight better say yes!