Finding the courage to wear a dress to work

Why do I need to do this? what am I trying to prove? I am sure many others will recognise an irrelevant or seemingly mundane thing that for some reason holds a strange symbolic importance in our transition?
I have worked as Jess for some time now and feel very comfortable in my presentation..no not my presentation..my skin.
But for some reason I soo want to wear a dress to work but Im kind of fearful… no idea why? maybe a bit my age and job Im in …. sales and over 50 ….but still sure there are heaps of women my age and in my profession wearing them..
nobody will bat and eyelid if I do I am sure but still Im apprehensive maybe its just a long forgotten symbol of i have made it when….

Hope things go well when you do

Jess, if you've been presenting as a woman at work, why the fear about wearing a dress or skirt? I am presuming that you wear make-up, jewelry, and feminine clothes to work now.
The only thing that should be holding you back is if a dress/skirt would be impractical for your line of work. Just make sure that the outfit is work appropriate, and good luck hun!

Jodie beat me to it. What do your co-workers already know? Do you already present in femme clothing/makeup/jewellery? If yes then a dress isn't that big a step or are we talking presenting as a MAID?

Jessica

I will assume for now you wear a top and pants to work. Would it be easier to wear a skirt with the top before taking the step to a dress.

Or maybe pick a day where you are leaving earlier so its dress for a shorter time. I have a feeling some women will just say with a big smile, its about time you wore a dress. :)

Good luck

You might find it easier to slowly arrive at your goal. Example: if you already wear women's clothes to work thst isn't as obvious as a dress, say a blouse and pants, then you might want to head in that general direction. A tunic that hangs below your butt coupled with whatever pants you wear now. Then, later on, the same tunic style with leggings. Once you have become comforts wearing that to work swap the tunic for a dress but keep the leggings. Finally, ditch the leggings. Congrats! You made it.

The trick is to read your environment. Sometimes we want to get all dolled up to spend time surrounded by women in drab outfits and zero glamor. Unless you work at a fancy firm, women today mostly prioritize comfort over any other consideration at work. You don't want to stick out because the attention can easily go south. It's one thing to express your identity at work and something completely different to be deemed a distraction or curiosity.

Wishing you the very best always.

Wear it when you are ready! You will love it once you start so be ready.

I've been wearing pink skirts outside my house while doing stuff in the yard to get used to wearing a skirt.

Where I work most women only dress up for special occasions. Someone is going to take pictures. Management is in town for a meeting. A company party. That sort of thing.

Marion

To those that have asked if I wear women’s clothes to work the answer is yes I present and work as a woman …make up as little as I can get away with and smart professional female attire there is no external issue with me wearing a dress just my strange fear or discomfort I do wear them socially when the mood takes me.

Quote:

---

Originally Posted by Jessicajane

Why do I need to do this? what am I trying to prove? I am sure many others will recognise an irrelevant or seemingly mundane thing that for some reason holds a strange symbolic importance in our transition?
I have worked as Jess for some time now and feel very comfortable in my presentation..no not my presentation..my skin.
But for some reason I soo want to wear a dress to work but Im kind of fearful? no idea why? maybe a bit my age and job Im in ?. sales and over 50 ?.but still sure there are heaps of women my age and in my profession wearing them..
nobody will bat and eyelid if I do I am sure but still Im apprehensive maybe its just a long forgotten symbol of i have made it when?.

---

I find it strange if you present as a woman, and everyone you work with has accepted it, then why the issue with a dress? It seems like a normal step to me. You have already crossed the difficult hurdles! (Oh, the evils in our minds!)

I would say go go for it, but do it well. Shop for a sharp, conservative, business dress and the proper accessories to go along with it. Maybe a nice skirt and jacket set. Don't half a** it!

Perhaps the apprehension has something to do with how other women present themselves at work. If the other women are wearing conservative pants and tops, then any women wearing a dress may stick out like a sore thumb. I saw that in my job before I retired. There had been a dress code for women when I was first hired; dress or skirt/blouse. After the "big boss" retired the women slowly slid into pants to the extent it was odd for a woman ever to wear a dress. Similarly, it was the same for the men. At first it was a dress shirt/tie and jacket (suit). I always wore dress slacks, collared shirt with tie. I stood out like a sore thumb after awhile. My recommendation to you is to start with a knee length dress in a color(s) that are not flashy to the eye. Dress so the eyes of others are drawn to you. That may help you feel less conspicuous.

I think I understand your apprehensions. Based on all that you have shared, it seems your colleagues are well aware of your transition and genuinely accepting. Thats the real world response, but even welcoming and acceptance do not entirely alter your inner dialogue?which has no doubt been shaped by long ingrained fears of rejection. You probably will not get past that inner fear until you finally confront it by wearing a dress or skirt to the office. Then, perhaps, your inner voice will say its ok.

Thanks for confiding in us, Jessicajane. It sounds like what you are suffering from is a fear present much more widely in society. For a lot of people a change in clothing or habit after a long period of time will cause anxiety due to fear of what people might make of the change.

Any woman who wore trousers exclusively for an extended period of time would likely come up against similar emotions.

Best of luck anyway - I hope we?ll get to read about it when you do.

You just want to blend so I suggest you to begin with a culotte (ie https://www.tarajarmon.us/shop/jeans...asty/4746.html) or a maxi black skirt (you are tall so it is for you !). Baby steps :)

I wore a dress into pick up my truck. I was told I can't drive like that. I said yep I know im going to change before leaving. I did get them to let me wear my athletic shorts to work in. As the rules say shorts are ok during the summer. And just because there is a skirt over it why not.

A few months ago I began wearing jean leggings to work. No one said anything. It was quite liberating. Last week I decided to wear some nails that I bought. Same thing, no reaction. I'm sure that people I work with have a good idea where i'm coming from lol. Wearing the nails felt awesome; even more so than the leggings. My wife, who is generally supportive, did not think it was a good idea and asked me not to wear them again unless I was fully dressed. Since she has been supportive over the years I agreed. Hopefully she will come around.

You?re way ahead of me. I?ve never presented as a woman.
But for you, would it help if you asked co-workers what they think if you wore a dress?

Jessica, the key question that strikes me is whether the women you work with wear dresses at times. If they rarely or never do, I can see why you'd feel awkward standing out by wearing a dress. But if they do, I'd say go ahead and join them!

(P.S. I'm not "out" like you, but just talking about this makes me want to wear a dress right now!)

I think it is one of many small barriers that over time we cross one by one to leave them behind. like when we let our hair grow and one day let it down, like when we prepare our ears for earrings, like when we start to wear little bits of makeup. Each of those moments generated great tension and strong emotions, but then they were left behind and forgot because nothing happened, it is what I would be feeling, I would just take the step and enjoy the moment

It's one thing to present at work as a woman in slacks and a blouse and be accepted.
I think the trepidation is that a dress is a no compromise statement of femininity. It's a line in the sand that truly says "I'm a woman" and it's not fear of expressing that, but the acknowledgement of another barrier crossed.
Just do it.

Fact is, most people everywhere like those who are comfortable in there own skin and even exhibit a bit of individuality
That is provided that the person is question is also very friendly toward others.

Just think about the kind of people you would most like to met...... a boring person or an interesting person .

BTW, many decades ago, I was working in a blue collar environment that also included many females who wore slacks.
However, there was one female who always wore a casual skirt. Everyone just accepted that and her right to be an individual..

This whole thread depressingly reveals why everyone dresses to the same standard: fear.

AngelaYVR, not always due to fear. In my work at my primary job, a skirt or a dress is impractical for what I do.

At my part-time job, a skirt would be acceptable, as long as it is knee length or longer. Dresses at both jobs wouldn't work, since a uniform top is required at both.

Well your situation prevents you from wearing a dress at both jobs, Jodie. But for Jess and everyone else not limited by a dress code (and people not at work) it certainly seems to be the fear of "standing out". It's like driving, everyone just waiting for the that one car to break the speed limit and then everyone follows.