Halloween - suspected of being a full-time cross dresser?

[caitlyn louisa]

I've dressed up as a woman and went out to parties at Halloween lots of times. Many of these times in the company of people who don't know that I'm a cross dresser and that I have no intentions of coming out to. I think that many people have suspected that I dress up regularly as I've had lots of comments like 'you appear to have had lots of practise walking in heels', 'you seem to be an expert with makeup', 'do you keep your whole body shaved all the time', 'you look like you are very comfortable dressed up like that', etc, etc. Has anyone had any similar experiences at Halloween?

[CharlotteCD]

If you've done it "lots of times" then yes, it's a bit of a giveaway...

[kimdl93]

I have never gone out on Halloween in girl mode, but I have a couple of acquaintances that have. Even though their presentation was less than spot on, there were speculations - some made at the time, perhaps in jest, and other private speculations later on.

[Geena75]

There was a Halloween episode of the TV show "News Radio" in which the station owner challenged them to dress up. Dave Foley's character dressed up as a woman, very convincingly. The other characters commented on how good he looked, but never suggested it was a lifestyle. Of course, it was just a TV show. (But that episode brought the pink fog down on me big time.)

[Leslie Langford]

There was a Halloween episode of the TV show "News Radio" in which the station owner challenged them to dress up. Dave Foley's character dressed up as a woman, very convincingly. The other characters commented on how good he looked, but never suggested it was a lifestyle. Of course, it was just a TV show. (But that episode brought the pink fog down on me big time.)

The best part was when his girlfriend kept looking him with a mixture of incredulity, awe and annoyance while exclaiming repeatedly "He's wearing my dress!!!"

[Alexis00]

As they say in “Clueless” - “Nice stems.”

[Jessica_NZ]

Reading through the comments I just had to share.

Threw a Halloween party weekend just gone, decided to dress as a french maid. Went to town with it, head to toe - as you do. Now most of the people I invited had seen me dressed before & were aware this was something I did occasionally. But, there were a few who did not know. Most of the comments mentioned below were said - you walk too well in heels, your makeup is very well done, you have gone to alot of effort etc. The clincher was how 'delicately' I kept moving my wig hair away from my face - dead giveaway evidently. Not that I was worried, I just owned it and carried on. They were really cool about it. I did also post a photo or two on social media - and have since had two different people say they have been asked by others if i'm a crossdresser haha I'm only out to small selection of people & have never been out in public - but maybe one day.

But I agree that I think it all comes down to confidence - if you get pulled up on it - it's how you react - or don't react- that can make the biggest difference. If you're that worried about being outed then don't go to too much effort.

[MonicaPVD]

Hi Caitlyn -

This is a question that we have all wrestled with at one point or another. It brings to mind a scene from the sci-fi movie "The Matrix". A young boy dressed as a monk is trying to teach the protagonist how to bend a spoon with his thought. After no success, the boy tells the guy, "Do not try and bend the spoon, that's impossible. Instead, only try to realize the truth. There is no spoon." (In other words, it is all in our head). Now, back to reality. We can consume a lot of energy and emotion in worrying about what others will think when they see us all dressed up at a Halloween party or we can "realize the truth": What they think won't matter by the next morning because it was just a passing, inconsequential thought. No one ever is sitting at the kitchen table on the morning of November 1 saying, "honey, remember Mike from accounting? Yeah, he's a crossdresser."

So just have fun and enjoy yourself.

[Stephanie47]

I don't necessarily think everyone treats it as an "inconsequential thought." For some it almost becomes their mission in life to somehow uncover the truth. In the office I worked there were some women who endlessly discussed whether so-and-so was gay. There was one guy who looked like the Marlboro Man. It irritated the crap out of two women who constantly speculated. The rest of us thought, "Who cares?" Then he showed up at the office Christmas party with his boy friend. With confirmation he was gay the women finally shut up. It was the same with another guy.

I have found whenever a guy knows too much about things in a "woman's domain" speculation arises. In general men are suppose to know all about car engines and sports; not women's "stuff." You could jest back that you had to do a lot of Youtube watching and do a lot of practicing rather than some ruse that you had help from a mythical cousin or girl friend.

Char's idea is a good one, especially if you go as an ugly witch. But, I'd suspect the same people would question "Why a woman's costume? Again!!!" Just have fun. Maybe, you'll attract an interested female.

[MonicaPVD]

This year for Halloween I have been invited to two parties where co-workers will be present. I am going to one as President Biden and to the other, much larger event, completely dressed as Monica with a minidress, hose, ridiculous tall heels, full makeup and breastplate. The plan is to preemptively raise eyebrows and kind of force my own hand into being more open about who I am.

[jessica33]

This year for Halloween I have been invited to two parties where co-workers will be present. I am going to one as President Biden and to the other, much larger event, completely dressed as Monica with a minidress, hose, ridiculous tall heels, full makeup and breastplate. The plan is to preemptively raise eyebrows and kind of force my own hand into being more open about who I am.

That sounds great . Does it means you will go to the office as Monica from now on .

[MonicaPVD]

That sounds great . Does it means you will go to the office as Monica from now on .

Jessica, That's not something I'm prepared to do yet. One step at a time!

[DTelia]

There are people who are never questioned, because of one thing…. CONFIDENCE.

I’m a confident person, but I wouldn’t be confident dressed on Halloween in public, and people would see right thru it. If you can own it - not go crazy over the top, but have fun…people will laugh, some may suspect (but more in a positive way - and it may even attract some because of your boldness and confidence)…do this and no one will care, and the ones that do, will be ignored.

My wife loves my confidence…she’s attracted to it. And honestly, the only thing she doesn’t like about when I get dressed is that I lose it…and that annoys her. I shut down, don’t tease, flirt, etc. I’m too aware of self and insecure.

[Sabine Janus]

to the other, much larger event, completely dressed as Monica with a minidress, hose, ridiculous tall heels, full makeup and breastplate. The plan is to preemptively raise eyebrows and kind of force my own hand into being more open about who I am.

How did it go?

[char GG]

One thing you might try is going out on Halloween in a woman's Halloween costume. There is a huge variety to choose from.

[Debra Russell]

....as long as you are cleanly shaved with perfect hair and makeup

[BlueTempest]

I have had eyebrows raised at me when I comment on GG's clothing or take part in conversation. Yes, I know what a peplum hem is, that red soled heels are often high end and I'm now learning what good makeup looks like.
My go to response in the past has been "well, boys often stare at girls, didn't you pick up some of the lingo too?". Now, I just shrug, ladies fashion is a hobby/interest of mine, so what.

[ellbee]

One thing you might try is going out on Halloween in a woman's Halloween costume. There is a huge variety to choose from.

Yep, I've never understood the "I'm going as a woman" costume... Unless it's an obvious "joke" (big fat hairy guy with a bushy beard, really bad wig, gigantic boobs, etc.).

But, people can do whatever?


Personally, when I used to do Halloween, I've always dressed up as a woman -- dressed in a Halloween costume.

And it's really easy to put together your own, using some things you may already have. Maybe grab a few accessories (e.g., witch hat, cat ears, etc.), and you're done!

[Leslie Mary S]

I guess I am lucky. I will never pass as a woman. I just dress how I want when I feel like it.

[MonicaPVD]

Stephanie, unless office gossip poses a threat to your livelihood, it is entirely inconsequential. People have been talking behind each other's backs since the Stone Age. It's what we do best!

[Sometimes Steffi]

I think that you get one free pass, as long as your presentation isn't too good.

Dress as a woman a second time and you're automatically clocked.

Think about Matt Lauer "crossdressed" three times on national TV.

Think about Joe Namath in Hanes pantihose. Is he or isn't he? And it was just once.

[Stephanie47]

Monica, you have to define "inconsequential." Whether one's job in threatened or not, to be the constant target of gossip and speculation about anything has a psychological toll on any person. I don't know how thick a person's skin has to be before it becomes an issue. Work place violence in the making? Hostile work environment?

[cosmolovesph]

Honestly, if you are willing to dress to go out - expect some to feel/judge and that is ON THEM... you do you... Now if you are afraid of the outcome (work, family, neighbors) than rethink it and maybe go out of town and dress!

[kimmy p]

Probably. Don't care.

[Raychel]

I did dress as an old woman for Halloween one year.
I will say there was questions about how good I could walk in high heels.