Crossdressing in the workplace

Hi Ladies! Long time lurker first time poster here. Need opinions on what to do. I started crossdressing when I was a teen like many of you so I won't bore you with details on how it got started. I am in the late 40s now and have a big collection of feminine clothes that right now is bigger than my male ones. I work in an office at a big tech company and the dress code is very relaxed (pretty much jeans and t-shirt everyday of the week). The girls are usually more dressed up based on what is currently trending. I am only interested in women's clothing and not on make up, lingerie so I started a few years ago incorporating some of these clothes to my outfits but one could say they look more gender neutral (for example, ankle booties with no heels, a women's version of a biker jacket or women's jeans). My wife accepts and even helps me choose some of the clothes as long as they are not dresses, skirts or very high heels which I am fine. We used to go out on the weekends to concerts, bars, theater, etc and then I would go a little crazier on the outfit (leather leggings, knee high boots, a nice cowl neck blouse for example). With the lockdown and most of those things we used to do closed for now, it has been a long time I don't dress up. Even worse with the whole working from home thing. Recently the office re-opened but still with limited number of people allowed and people can go on a voluntary basis. I can go once a week and this as an opportunity to dress up (office is always nearly empty). One day I decided to wear cropped pants, flat ankle boots, sweater and a vest on top. A lady came and asked what was going on that I was all dressed up and started mentioning all items I was wearing lol. Last week I wore another pair of flat boots, a pair of ankle pants with a paperbag waist and a top. The same lady did not say anyrhing the entire day but when we were leaving the building she mentioned that she saw on the news the other day a guy that wears skirts and heels to work and he is srraight, he just likes the clothes. Do I keep pushing the envelope, or should I stop crossdressing? My fear is next time she will actually ask more direct questions.
Thanks
Courtney

Welcome to this forum. I tend to live in the real world. Although, in my state the law protects this sort of expression as well as anyone under the banner of LGBTQ that does not confer acceptance on a personal level. I always consider what may be the negative consequences of anything I do. Would promotions be denied to you in a subtle manner? That sort of thing. If you're a low level employee with no aspiration I would think you could push the envelope as much as you want. If your economic status maybe in peril, then that is a serious consideration. In recognition of a person's rights I have read an employer may legally ask that any interaction with a valued client does not lead to confusion. That seems to make sense. Don't meet one day in a man's three piece suit and white shirt, and, the next time in dress, heels, wig and makeup. Rather than asking us I would suggest asking your wife as she will be the one bearing the burden of your decisions.

Absolutely, you should keep pushing the envelope, even upping the ante by wearing a nice skirt and heels.. Its nobody's business what you wear, as long as its not too revealing or inappropriate, and from your description it isn't. What is inappropriate is the questions of that coworker. She's way offside. I think you need to ask her who else she grills so thoroughly, and tell her she's making you feel uncomfortable, especially because your clothing choices have ZERO bearing on your work performance

I disagree with the last two posters.

I think your co-worker is curious and her comments indicate to me that she is open minded and is trying to communicate that to you. She may be trying to tell you that she is an ally. If she asks, I suggest you give her the truth; that you like the look and the feel of the clothes. If it's a tech company, they probably are very open minded.

Besides, you are wearing the clothes because YOU DO want a reaction, right? And you are surprised when you get one?

As to living in the real world, the higher up in an organization, the more protected you are, because you are more valuable and have more power. If you are on the low end of the totem pole, you are more expendable.

And asking your wife because she would bear the burden? How sexist. How 1950's.

Also, no a company doesn't have a legal right regarding presentation with a client, as ruled by SCOTUS recently.

Instead of asking us, I suggest a visit to your HR department and see what they have to say about your dressing choices. I'd also probably ask your boss, and get his or her ok.

Those two sources can give you a lot more guidance than any of us.

The analogy I like to use is: Would you ride a bicycle on the roads during rush hour traffic? Yes, in most states, you have the legal right to an entire lane on a bike. You are protected by the law. However, is it a good idea? Should you endanger yourself as a bicyclist--because it is dangerous--even though you are legally protected? Or, maybe, sometimes it's just "better" if the bicyclist waits until either rush hour is over, or they find a quieter, safer path to ride.

Agree with Danam. Make sure that you are not experiencing a pink fog.

I too agree with Danam. Just because there is no clearly defined dress code and expectations you are not really free to wear whatever you want. How many women come to work in bikinis just because they look great in a bikini? I think a bit of mix and match is fine so long as it is not an "in your face" kind of thing that looks like a protest. The person featured in the news that dresses femme below and masculine above is in Germany and not the U.S. Standards and expectations differ and pushing the envelope carries with it a bit of risk that may not be justified when it comes to your employment. So, I think what we are saying is that you need to use your head in how you present yourself - be rational while considering the emotional things you feel. But let reason be the primary factor in what you decide.

I think the curious workmate may or may not be interested in the person who expresses the way you were dressed. From the evidence she might be supportive or might not be. Be friendly and nice until you can tell more about her motivations and then adjust accordingly while, once again, keeping reason as your guide. Unfortunately, in this divided and crazy world you can never be sure of anyone's motivations until you get to know them in other ways. In all probability, she is just curious, but I recommend you not simply assume that. The workplace, unfortunately, operates in a bit of a political perspective. Some places not very much; other places a great deal.

And welcome to the forum. I was a lurker for sometime as well, but then I joined and on the whole it has been a good experience.

"As to living in the real world, the higher up in an organization, the more protected you are, because you are more valuable and have more power."
Are there highly compensated LGBTQ persons in your organization? There is strength in numbers. Where I work there have been managers in key positions for decades.

Ironically my wife set me on the path to dressing in feminine clothes as we realized that there was no way I was going to dress well in men's clothes. I wear size 2 clothes right off the rack, which would be XXS/XS in Men's clothes.
That was ten years ago and I'm still here while many of my co-workers of that time aren't around. When she passed I realized I had saved way more than I needed for retirement.



Marion

Do you have a "career" or just a job that you can replace at any time?

Dressing "weird" at work can hurt your career and chances for advancement. Don't quote laws, realize reality. If people are uncomfortable dealing with you, you won't go far even if you don't get fired or laid off.

If it's just a "job", do what you want and get a different one if necessary.

Courtney, this is about u, not us. I'm a closet dresser. I have no desire or need to go out in Vanilla Land dressed! I don't need more flack or attention when I'm out shopping or eating!:doh:

However, u may feel differently. My advice is, dress in whatever fashion u FEEL MOST COMFORTABLE!:thumbsup:

As a crossdresser, you have a choice. You may desire being dressed at work, but you don't have to be. If you judge that there will be no substantial impact to you career status, by all means go for it. Short of that, though, why would you put at risk something so important as your livelihood?

I have trouble understanding why someone would crossdress in public, or at work, and seem to be surprised when someone questions it. Seems to me I would be prepares for that before I stepped out of the house.

As for work, check with HR, and your supervisor. Keep in mind if they have issues it is best to find out up front, than months down the road when it might be too late. Perhaps your employer can't prevent you from dressing as you like, but they can hold you back or let you go for "some other reason".

The culture of your company has a lot to do with how you will be perceived. Realize there is the culture of the larger corporation and the culture of your individual location. So while the corporation might want to project as an inclusive organization the local site reflects the community more and so any judgments about you will be made from that perspective.

If you decide to push the envelope to test boundaries you might jeopardize your position if you are not careful. If you want to push the envelope to truly express yourself and you cannot be happy unless you do, then you have to decide if the corporate culture will allow that. You may have to look for a new job that will allow that expression.

She obviously has noticed the gender of your dress style. Your company policy has alot tod with where you go from here. BUt has far as the questioning lady Come out to her. JUst say something like "I'm letting my fem style come through" or I'm a transvestite.Straight out come out. Then see her reaction, it should be interesting. You may get a dressing friend, maybe her husband is one of us and they're looking for a friend or maybe she just won't believe you

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Originally Posted by TheHiddenMe

I disagree with the last two posters.

As to living in the real world, the higher up in an organization, the more protected you are, because you are more valuable and have more power. If you are on the low end of the totem pole, you are more expendable.

And asking your wife because she would bear the burden? How sexist. How 1950's.

Also, no a company doesn't have a legal right regarding presentation with a client, as ruled by SCOTUS recently.

Instead of asking us, I suggest a visit to your HR department and see what they have to say about your dressing choices. I'd also probably ask your boss, and get his or her ok.

Those two sources can give you a lot more guidance than any of us.

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Discrimination can more subtle. It does not have to be overt. People just do not come out a blissfully ignore the law. A complainant has to establish a pattern of behavior. That is not as easy as it seems. The court case before SCOTUS was a case of overt behavior. Frankly, in order to get into the protected class within an organization you have to get your foot in the door. I don't believe SCOTUS was saying an employer cannot recommend some sort of uniformity in presentation. That may make an interesting case. Is one really a transgender man or woman on Monday and not Tuesday?

I don't see sexism coming into play at all if a spouse asks is or her spouse for an opinion as both spouses end up bearing the burden of the other's actions. It would rather 1950's if the guy just does what the hell he wants to do and tells his wife to just suck it up and stay in the kitchen. Or, maybe, "Hey honey, we're moving from New York to California. Pack your bags. The moving van is coming tomorrow!" That's 1950's. Not just running rough shod over a wife. I have seen a lot of that on this site. A MCP can also wear a dress and heels. And, also I seen a lot of input asked of a wife before the husband does something that may affect his wife.

Yes, going to HR is always good advice. If there is a rule in place, supported by SCOTUS or not, you do not need to ask your boss whether it is OK. You ask HR whether it is OK or not.

What are the question(s) you are afraid she will ask?

Crop pants and ankle pants are further than metro look and will definitely raise an eyebrow.

It sounds like you are caught up in the pink fog. This can be both positive and negative, so be aware of it.

What is culture?
-- annual/bi-annual harrassment training?
-- company policy and practice towards non typical clothing styles?
-- is she in your org group? Sounds like not, so typically safer than someone in your group.

What does your wife think about this? Does she see any blowback?

How far do you want to go? Did you really also want to wear joga pants or leggings or skirts? Sounds like yes.

Is it fair to say that you wouldn?t really object to being outed?

Big thanks to everyone. It is great to see different points of view. Some more background to my original post and clarifying some of your questions: I have been with this company for 10 years and I am in a managerial capacity (without direct reports). It is a tech company with over 400 people. There are a few TG people in Senior Management positions (our Chief Marketing Officer is TG) and even though some people dress more ?fashionable?, I?ve never seen any guy wearing a skirt for example.

My wife is ok with me crossdressing as long as it does not involve skirts, make up or very high heels, which is a compromise I am ok with. I agree with some of you who mentioned the ?pink fog? thing. It might be correct since I have not been able to dress up since the lockdown (there is pretty much nowhere to go) but I still wear yoga pants and hoodies to go shopping, run errands and even go to work sometimes.

Now, with this whole situation, the office is mostly empty with the majority of people working from home, I then started ?pushing the envelope? a little bit because these clothes make me feel comfortable and I just like them over regular plain men?s jeans and polo shirts. As mentioned above, I am not a fan of skirts (just my preference), so I would not wear one to the office, but instead of what used to be clothes that could make one not sure if it is male or female, now these are clearly female (elegant, modern and presentable) and I would never wear these to a customer meeting.

Here is an example of what I wore today to work and there were less than 20 people in the office.

It is getting cold so I wore this exact vest (scroll down to see):

https://www.aritzia.com/en/product/alta-vest/75562.html

Paired with wide leg leather pants, black blouse and flat boots just like this picture:

https://www.pinterest.ca/pin/570057265313087618/

Funny thing is that I was walking and someone from HR passed by, said hi, how are you and went on with whatever they were doing.

Now regarding the co-worker (who was not there today), she is part of my department and we know each other for 7 years and became good work friends. I guess my fear is that I have never told anyone, except my wife, about the crossdressing, and if it gets to a point where she could ask me questions like ?are you gay?? or ?you know these are women?s clothes, don?t you??, that would be the first time ever I would need to answer these types of questions.

On the bright side, I left work, stopped at the outlet mall, went to a couple of stores and one of the salesperson commented that I looked amazing. And that made my day.

Take care everyone.

Courtney*