Halloween yesterday. For years I wanted to dress up as a woman, I never did. I didn't want to admit to anyone that I wanted to. So, every year, no dress-up at all - I simply avoided anything about the night.
On to last night, My wife asks me if I'm going to dress up as a woman .. yay! .. NO! ... She asked at 7pm last night, nothing for my hair, no make-up, no shoes, no proper dress or skirt, no bra. My wife is much too small and she doesn't wear make-up. I had nothing that would add up to fully dress as a woman.
We went out but I was miserable all night, I still feel like crap today.
It sounds like your wife might be O.K. with it. Lucky you!
Make a plan for next year. Right before Halloween go shopping at thrift stores. If it makes you nervous, just tell the shop people it's for Halloween. You will be surprised at how helpful they will be.