Halloween may out you!

[Nikki A.]

I disagree with the premise that if you dress you're a CD. If you dress as Santa or as an elf on Xmas does it mean you want to be a jolly fat man or live at the north Pole.
I've dressed for Halloween as a female, but I've always gone as a character or period piece (hippie, dressed as someone else) this way I can do my best and have plausible deniability especially if I have a GG or SO working with me.
I wouldn't just dress as a female, I think that most females can tell when you've done too good a job or you're just too comfortable.
It's the little things that out you. I did Mimi (from the Drew Carey Show) one Halloween for two different parties on two days. The first (work party) my hair stylist did my wig and helped with the make up (plausible deniability), no problem. The next night I did it all myself and went to a friend's party, I was a hit to say the least, I did have one or two women ask who did the make up, I said myself but that I was shown how and given the makeup I would need, the day before and I just redid it. One just kept saying how good I was with the foundation, no lines and so well blended. Maybe I outed myself a little by doing too good a job.
No female get-ups for a bit. Maybe next year, this year I didn't do the holiday.

[JamieG]

To answer Isha's question:

I have dressed up en femme twice for Halloween: 10 years ago and just this past year. I've also been in three charity drag shows over the last five years. I've posted photos of the latter on my male Facebook feed. Not once has someone asked me if I'm a crossdresser. Nor has it gotten back to me that people are "talking about me." Is it possible that some people suspect? Sure. But I have had no negative consequences, so it doesn't really matter whether anyone does or doesn't.

Now, a few caveats: all five of these occasions I was with my wife. So that may provide some cover. Also, my wife and I had (before kids) a reputation for doing elaborate costumes, so a good drag costume could be seen as just "upping our game." If you've never dressed for Halloween, and then suddenly go super-femme three years in a row, then people might start to talk. But otherwise, I think there is little to fear.

Jamie