What to Wear to Work – Dressing While Butch

What to wear if you are butch?

What to wear if you are butch and transgender?

After five months of slumming I laid out work clothes. I want to feel comfortable going back to the office. I tried on a few permutations of jeans, button down shirts, and sweaters in front of the full length mirror with the lights on. Five years ago this would have been a humiliating and depressing task. Now, I only wish I had sent my sweaters to the cleaners in April instead of throwing them in a heap to moulder.

Except for senior management, new employees, and ambitious scum, no one at Transit dresses to impress. There is a lot of cheap polyester. Dated and out of fashion. There is no incentive to buy new clothes if you can still fit in your old ones. There is no written dress code. The expectation for men is a shirt and tie; the expectation for women is nothing that I would wear. My perpetual dilemma.

In the worst years of my dysphorias (gender expression, weight, breasts, and body shape) the worst part of my day was getting dressed to go to work. No matter how drab an outfit I put on I felt like I was wearing a neon sign that said “overweight butch lesbian with no sense of style.” Bright colors were worse. I wanted to disappear but I felt huge and ugly. I knew I was wearing women’s clothing and it felt wrong. This went on day after day.

I searched for women’s clothing that looked liked men’s clothing. I looked for masculine colors in large petite sizes (a contradiction in terms but think short and fat). There was not much to choose from and I ordered what I could stomach. I loathed all of it. It is hard to look your best when you don’t like what you are wearing.

Once, I took out all my shirts, turtlenecks, sweaters, and slacks and laid them out on the bed and played mix and match. I couldn’t try them on and look at myself. I could only look at my outfits detached from my body. I made a list of the best combinations.

It bothered me that I could not reconcile myself to wear women’s clothing or find a professional looking solution that I didn’t despise. I considered myself butch, but I didn’t want to think about what it meant that I could not feel like myself in a pair of women’s pants. I did not want to admit that my dysphoria was so bad that the only way I could hold onto myself was by wearing a pair of jeans.

One day my boss called a staff meeting. He told us he was leaving to take another position in another city. We stifled our hallelujahs. He told us who the acting boss was. I didn’t hear anything else he said, all I was thinking about was that the acting guy was a wuss. He would be afraid to confront me if I wore jeans to work. I wore jeans. A few months later he was officially given the job, and although it annoyed him, he didn’t say anything and I didn’t change.

Gracie gets in the picture.

Gracie gets in the picture.

For my return to work, I narrowed my options down to two combinations, and went for the one I am most comfortable in. An orange and white stripe shirt (custom-made), a camel V-neck fair-isle sweater, dark blue jeans, and brown Keen loafers. I’m going to have more shirts custom-made after top surgery.

I may not win any dapper awards, but at least I won’t trigger an anxiety attack if I catch a glimpse of myself in the mirror in the Ladies’ Room. I’m not responsible for anyone else’s reactions.

Note: The drawing at the top of the post comes from Edith Head’s 1967 classic How To Dress For Success (which is a better read and more fun than John T. Molloy’s horrific The Woman’s Dress For Success Book).

 

27 thoughts on “What to Wear to Work – Dressing While Butch

    1. Jamie Ray Post author

      True. But even with no restrictions, I’d feel odd showing up in jeans, a T-shirt, and a Flannel shirt because it is too far removed from what the men wear. Some of the younger guys in planning do a pseudo hipster look, but they are low on the totem pole and tend to look for another career after a few years (they look at what the future holds and run the other way before middle age catches up with them). It has always been a balancing act between feeling at home in the clothes and not dressing in anything that felt too out of place. As long as I can wear jeans I can manage.

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      1. The Final Rinse

        I am fortunate enough to have a partner with very good fashion sense, and design sense. When I go shopping with her, she finds things that I would never imagine work for me: things that I would entirely dismiss. Yet they work, and emphasize my own self image in an unexpected way, and don’t challenge my intense aversion to men’s clothing.
        So here is what the nosy me thinks you need: a person with some fashion sense, who understands you, and who understands the person whom you are trying to show to the world, to go shopping with you.
        Sorry, mine is not for rent. 🙂

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      2. The Final Rinse

        I will relay the offer. 🙂
        I think that it is possible to get trapped in one image of yourself, when there are other possible versions of the outward you, that are really more suited to you. Did that make sense?
        I am also thinking that everything will be easier for you post surgery.

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    1. Jamie Ray Post author

      I held off buying work clothes because I was retiring (or so I thought), and I held off because I was losing weight, then I held off because I’m having surgery. I haven’t bought a shirt for work in about three years! So I fit right in with the rest of my co-workers except that my shirts are not made out of cheap poly…

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  1. dexxwizard

    I am only starting my real journey but understand the frustrations of having to wear men’s clothes to work when I want to wear a smart dress and heels for example. I would go as far to say I get jealous seeing the girls at work.

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    1. Jamie Ray Post author

      You wouldn’t be half as jealous if you saw what the women in my office wore – not too many smart dresses and cute heels at Transit. I am very, very, lucky that I could go to work (the last 7 years) in jeans instead of trying to find women’s slacks (men’s didn’t fit properly although now that I weigh less they might).
      I think work is the most gender oppressive environment. Now I could ask myself why I would go back, even just once a week? Hmmn. Good question and long complex answer to be thought about at another time.

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  2. The Little Butch That Could (TLBTC)

    The dress code where I used to work was probably the best, for me any way. I had no trouble with it. Every work day I got to wear scrub uniform bottoms, a polo shirt and sneakers.
    Good to see Gracie, she makes me smile. Cheers.

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    1. Jamie Ray Post author

      If I try to take a picture of Gracie she balks. If I try to take a picture of something else, she tries to get in it. She considers that bed “her day bed”.
      I hope you find another position soon, and one that respects who you are.

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  3. genderneutral

    overweight butch lesbian with no style – love it! This is exactly how I felt all my life until recently. Being self employed I have always worn extremely casual clothes. Most of my clients love me for it. To day I have stepped up to something more close to business casual. It actaully feels good. Having a chest vs breasts has done wonders. I wonder who custom makes these shirts for you. Mens shirts definitely do not fit right my small frame.

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    1. Jamie Ray Post author

      I’ve had them made in two places. Brooks Brothers (the one in the photo) does custom shirts through some of their stores – they are not really custom – you choose the size (reg or petite) the collar style, the cut (full, tailored, slim, etc.), pocket or not, and select the fabric – the only exact measurement they take is the sleeve length. The shirt buttons like a woman’s shirt (opens to the left) but it works for me. The other custom shirts I have are from CEGO NYC, and they were fully measured – neck, arms, length, hips, chest, etc. plus choice of collar, cuff, fabric, placket width, and I asked them to open to the right (man’s side). Charles Goldberg, who runs CEGO, is very nice and seemed totally comfortable with me.
      I want to try a company called “Proper Cloth” and I may go there or back to CEGO after surgery to have some shirts made. You can do Proper Cloth online or go in (if you are in NYC) to be measured. I think they allow for a hip measurement when you refine your size, which is critical for me (along with sleeve length).

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  4. txbridgefarmer

    Good for you! I’ve always been fortunate with regard to my wardrobe at work. In the Army, it was the regulation BDU that was made for men. Then in the “real” world it’s always been work boots and jeans. My only dilemma, like you, has been when I have to dress for meetings and such.
    Here’s to a terrific first day back!!

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    1. Jamie Ray Post author

      Transit is similar to the Army without the uniform. A lot of former soldiers and Reservists, and not a lot of coddling if you are uncomfortable with the environment. But, if you don’t mind getting up early and showing up on time all the time, it is not a bad place to work. Plus, great security, benefits, and pension. Which is what I kept telling myself everytime I got dressed…

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  5. Lesboi

    I’ve always thought having a job that required wearing a uniform would be cool…postal worker, ups driver, soldier, etc as long as skirts and heels weren’t involved. I’ve been lucky to work mostly in shops where the dress code is “whatever you don’t mind getting messed up, ripped or stained.” Usually, these days it’s jeans and either a t shirt or polo but I’m trying to expand a bit into some men’s chinos and button downs. I’m looking forward to getting a couple light sweaters for the winter months. Anyway, I think, as a consultant, you can wear whatever the heck you want (within reason, of course! No pajamas or slippers lol). The outfit in the picture looks perfect. Gracie looks like she approves too.

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    1. Jamie Ray Post author

      My office was considered a “great place to work” because there was no uniform and no serious business dress code. Here comes the stupid sentence “if I was a guy I probably could have made my peace with a shirt and tie” but maybe I would have always had it half unknotted and complained about it and tried to wear turtlenecks and polos…I’ll never know.

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    1. Jamie Ray Post author

      Right, that is why I said it was horrific. I actually remember looking at the book when it came out and thinking there is no hope for me whatsoever. Molloy was adamant about women not wearing pants in the work place in the 80s!!!! He was into trying to find a corporate uniform (skirt suit) that women could adopt the way men could adopt a suit and tie, and he hewed strictly to the binary – and to women dressing to get corporate male approval. At the time I was wearing Brooks Brothers button downs and Talbot wool slacks with penny loafers to work – short hair, no make-up, no jewerly, no floppy tie/scarfy thing. I would have scored a zero with him (or been another one of his how not to charts).

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  6. Skip To The Loo at UNSW

    It’s ironic to see that some workplaces still expect women to wear skirt and make-up or have that as a mandatory policy, even though it’s already socially acceptable for women to be walking around in pants. I’ve been careful with choosing companies to send job applications to, avoiding any company that might force me to wear a skirt. Same problem with work toilets. I hate walking into a female toilet when I look like a dude. It either makes the people who see me think they should be elsewhere, or think I should be elsewhere.

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    1. Jamie Ray Post author

      Transit doesn’t really expect women to wear a skirt, they expect you to look “professional” but they really think “professional woman” not “professional non-binary butch with issues”. I won’t wear anything with frills, darts, princess seams, etc. and it is nearly impossible to find work clothes that don’t smack of some clear reminder that the outfit is for a woman. The solution, which I did for shirts, is custom made, but that is very expensive for an entire work wardrobe, versus one suit for weddings/funerals/interviews (I don’t have that one either). If I bought a men’s suit it would have to have a lot of tailoring done, and I’m not sure it would still look like a men’s suit by the time they were finished with it.

      I linked in the post to an old post I wrote about accidentally freaking some woman out in the Ladies’ Room at work – where I usually felt safe because everyone knew me.

      Good luck with your work to get the university to provide some bathrooms that are for use by all students/staff.

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  7. krisalex333

    I am totally jealous of that sweater – love it! (Maybe Gracie will post it o me while you are out working!) Transit is a foreign (concept) company to me, being stranger your lives as US citizens. Maybe you could explain to me in short (via email is fine if you don’t want to bore your other readers)? Or just post a link to where I can read up on what exactly you do?

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  8. Georgeann

    I don’t know what I would do if I couldn’t wear my favorite blue jeans and flannel shirt at least a couple of times a week! Probably end up in jail for some kind of embarrassing public tantrum. Clothes are such an important part of identity, even when we try to pretend that they are not. I love the picture of Gracie with your cute clothes! I think we have similar wardrobe tastes; the striped shirt and sweater is something I would wear regularly. Once you find your style, you gotta wear what makes you happy. 🙂 Years ago I bought and absorbed Tim Gunn’s Guide to Style, and discovered that my fashion icons are Katherine and Audrey Hepburn as well as Ellen DeGeneres. Figuring this out has saved me so much confusion and angst over my wardrobe — though I am still looking for the perfect pair of jeans!

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    1. Jamie Ray Post author

      I’m fine with my style until I have to get dressed up, and then I get stressed out. Fortunately, I have few occasions that I need to get dressed up for – but each one is a trial. Note that by “dressed up” I mean jeans are not appropriate! The book I referenced by Edith Head should interest you – she dressed Audrey Hepburn!

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  9. liamanthony2014

    That striped shirt! I have one almost exactly the same, except that I got mine from H&M. (I like shopping there because they actually have menswear small enough to fit me.)
    But I totally feel your pain. Clothes have been a nightmare to me for ages, and it’s only since I could allow myself to be me (instead of being my female impersonator) that I’ve found clothes I really love.

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