The Perpetual Search for the Perfect Shirt

Bodhi, the Shiba Inu model from Mensweardog.

Bodhi, the Shiba Inu model from Menswear Dog.

Winter is over. I went through the winter wearing the same baggy button down shirts that I wore last year. I wanted to wait until after I had top surgery to shop for new ones. I’ve always worn loose shirts to hide my chest. I don’t have to do that anymore. I need a new magic shirt. A shirt that can transform a bad gender day into a rainbow unicorn.

I’m still an odd size. I went to Macy’s and tried on men’s and boy’s off the rack shirts. Some were too big, some were too small, and none were just right. And it looks like I’m going to have to get used to my nipples showing when I wear a T-shirt.

I used to try to shop in the women’s department. This was self-defeating because it is nearly impossible to find men’s clothing there. I had a lot of rules. No darts, no princess seams, no little breast pockets, no frills, no ruching, no loud colors, no 3/4 length sleeves, no decorative buttons, nothing cut on the bias, and no polyester. In other words, I wanted a man’s cotton shirt. Sometimes I’d luck out and find something from Ralph Lauren, or I’d order from LL Bean or Lands’ End. I rarely found what I wanted. The lack of choices pissed me off.

There were thousands of shirts, exactly what I wanted, in the men’s department. Just out of reach. I tried to talk myself out of them. They never fit. If I got the chest right, the shirt was too big around the neck, too tight around the hips, and too long in the sleeves and torso. Tucking it in and rolling up the sleeves helped, but no amount of tailoring was going to transform it into a magic shirt.

The solution was to buy shirts made to order. Custom shirts are a trial and error proposition. It takes a couple of tries to get the fit right. Not all fabrics look good on me or drape right, and I can’t try them on until it is too late. There are a surprising number details to specify (collar, cuffs, yoke, placket). It is easy to make mistakes. But when it works, it works. My favorite shirts are custom.

My butch friends and i don’t talk much about clothes. I don’t know where they buy their shirts. We don’t talk about shopping. Maybe talking about clothes is too girly for us. The guys I work with talk a lot about clothes, although mostly they brag about how little they paid (as in Macy’s had a 30% off sale, and they had a coupon, and the jacket was already marked down, so they spent next to nothing for it). I wouldn’t tell the guys at work that I paid $150 for a shirt. Or that it has magical properties.

The shirt maker I used before only makes dress shirts. I found a new shop that is less expensive and also does custom casual (denim, chambray, flannel, linen). I’m in the middle of the process right now. I went in and got measured (wearing a tight T-shirt), looked at their swatch books, picked out a fabric for the test run, and selected the collar and cuffs. The first shirt they made was disappointing. It was too tight around the neck and chest and too short in the torso. When I brought it back, they agreed. They adjusted the order and I’m waiting for magic shirt 2.0. The first refitting is free; I hope this time it comes out right, or at least close enough. Once they have a good pattern for me, I can order shirts in my size in any fabric they carry.

When a shirt fits I feel handsome in it. I feel masculine in it. I feel normal in it. I don’t feel like a sheep in wolf’s clothing. I wish I could say that I feel good all the time and it doesn’t matter what I wear, but it is not the case. Sometimes I need a magic shirt to remind me that I am fine and that everything will be OK.

Notes: If you want to look at pictures of a cute dog in menswear, Menswear Dog is a fun Tumblr site. It has great outfits for boys and their dogs.

Last year I wrote about the exact same problem with shirts including my ongoing obsession with which side of a shirt the buttons are on. As Yogi Berra would say “It’s like deja vu all over again.”

25 thoughts on “The Perpetual Search for the Perfect Shirt

    1. Jamie Ray Post author

      In NYC there are several options – there are shirt makers who only make shirts custom (CEGO), there is Brooks Brothers which makes semi-custom (fabric, collar, cuffs, sleeve length but standard torso size) and then some on-line options. My latest and yet unfinished attempt is with Proper Cloth – if you go to their web site you can see what they are about since they also do on-line orders. They use a lot of measurements (which you can supply) and most importantly for me they can make the hips wider than the chest if you dig into the hidden measurements section. They were very nice to me and I felt welcome there (since I am not exactly their target customer).

      If you order from them (or any other on-line shirt maker) I’d recommend going with an inexpensive plain fabric first – so you are not out the maximum if you take a couple of stabs to get it right. Proper Cloth starts at $80, but by the time the shipping and handling is done, it is more like $100. If you do have a shirt that you like, they can copy the dimensions.
      There are some other on-line and mortar shirt makers that have good reputations, like Ratio in Denver.

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  1. Widdershins

    Women’s clothes – my favourite bug-a-bear with pants is NO POCKETS! What? Women don’t need them because they have purses?

    Glad to hear you’re getting your 2.0 on! 😀

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  2. J.D.

    This brought back memories of shopping for a white shirt to wear as part of my band uniform (decades ago before I knew I could escape being female). It seemed everything had stupid girly frou-frou on it until I found a perfect plain shirt … by Calvin Klein. Yuck! Twice the price and labeled with someone who said his models were “draped to be raped”. I went home empty-handed that day.

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    1. Jamie Ray Post author

      I’m trying to learn to stop banging my head against the wall. One of the things I hated about shopping in the women’s section was that sense that there was something wrong with me because nothing appealed to me – and the sense that the reason nothing appealed to me was that it was in the women’s section – that the identical item would be OK if it was from either a unisex store or the men’s department.

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    1. Jamie Ray Post author

      You’ll have to get Link to design you one. One of my readers (Pixie) sews and can make their own. If I was precise/neat enough and serious enough, that would be very appealing. In my mind it would take me years to learn how to do that (as well as several trips to the emergency room). And I’d get to buy equipment…

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    1. Jamie Ray Post author

      Thanks for reading and commenting. The perfect shirt is symbolic – everyone I know who is trans has something they obsess about (whether is is chin scruff, washboard abs, or in my case finding a shirt).

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    1. Jamie Ray Post author

      I remember you writing about getting them. I took a look at it and it seems like a good site. Did you measure your body and let them build you a shirt based on your own measurements or did you measure a shirt you liked and give them the shirt measurements?

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      1. Tea With Ess

        I measured my body since I didn’t have a shirt that fit me at the time. I must say that I’m impressed at how well fitted the shirts are, and I think they are aware that they have FtM customers. When I put in my measurements (marked as “male”) the site auto-filled my measurements very accurately after just a few measurements – including chest and neck size. ALWAYS double check every measurement though, and be truthful. My shirts look like any other nicer of the rack shirts, as you would expect them to look on a man, but when I iron them I can see how awkwardly they are cut to make room for my hips and it takes some getting used to to iron them flat in the seams.
        A pick of one of my shirts can be found in my post ‘who is he?’, http://www.teawithess.com/2015/01/13/who-is-he/

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      2. SashaQ

        I have a couple of magic shirts from Tailor Store, too. I measured a shirt I already had that was almost what I wanted and adjusted the measurements slightly.

        My measurements didn’t auto fill accurately, though, so they sent me an e-mail to check that the figures I had entered were what I wanted before the first shirt was made, which did make me feel a bit weird, but the shirts fit just as I like, so that was good.

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  3. PlainT

    Uniqlo (sometimes) has women’s shirts with no darts/seams. They are sometimes nipped in at the waist but you might be able to get that tailored. I’ve found some good stuff at H&M men’s or on Amazon from the boys’ section. Other than that I usually go for knits; I recently got this at H&M: http://www.hm.com/us/product/16087?article=16087-J. It looks more put together than a t-shirt but more forgiving than a woven shirt.

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    1. Jamie Ray Post author

      I’ve had mixed success at Uniqlo – good T shirts, but I’ve not found good long sleeve shirts. H & M is cut too tall and slim for me – or maybe I’m just too short and chunky for them, I gave up them before top surgery, but it may be worth it to see if I can get into a Small now. Their mediums are cut for someone who is 6’2.
      I have had some success with boy’s XL (18-20) – at some point I’m going to have to eat my words and complain about the lack of interesting colors that boy’s clothing comes in.

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  4. Kris

    My huge frustration is to get men’s shoes that fit. I wear a size 3-4, not sure if it is UK or what measurement, but my feet are really small. Men’s shoes start at a 6, way to large for me. Now I have to wager into the boys department. “Can I help you, ma’m? Looking for shoes for your son?” Instant dysphoria and anxiety. Instant retreat. Gathering courage is a slow process. Sigh.

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    1. Jamie Ray Post author

      I’m a US Men’s 7 (UK 6 ) and it is hard for me to find my size in a store (it used to be easier but they feed kids too much and they grow too fast) so I can imagine it is impossible for you. I now order a lot over the internet (too bad Zappos isn’t in South Africa -free shipping in both directions), but I’d rather try on in a store – even with condescending sales “help.”
      I’m very fussy about shoes fitting properly – I walk a lot and I don’t want to rub up blisters. And equally fussy about them not being identifiably women’s. And I agree with you, shoes are worse to shop for because you can’t take them to the tailor or wear them baggy.

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    2. SashaQ

      Yeah, I get boys’ shoes too – last time, my usual style had been discontinued, so the salesperson showed me the catalogue, and asked me if I wouldn’t rather have girls’ shoes, which was instant dysphoria, as you say. I did directly say no, boys’ shoes are what I want, so I was successful in finding something else but it wasn’t the most enjoyable experience…

      The time before was much better, as the owner of the store (who is older than the salesperson) was very respectful as well as helpful, so it was a pleasure.

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  5. txbridgefarmer

    I hate shopping for the exact reasons you mentioned. If it fits in the chest, it hangs off my shoulders., etc.
    I lucked out and found. A seamstress here in Beaumont and Julie had one back home that I go to now. I buy the shirt I like that fits in the key areas and then they simple alter it. Taking in the sleeves and such. Much cheaper than having an entire shirt made. It usually only costs me about 30 bucks. So, if I buy a shirt for 40 I’m saving quite a bit. But then again, I’m sure there are those who think 70 dollars for a shirt is too much too.

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  6. dmcco01

    I am SO struggling with clothes right now, and my self-confidence about myself and my identity too, I guess. I’m a cis straight woman and I suppose I’d call myself genderqueer. (Still toying with that.) I’ve started dressing more male, which is how I feel most comfortable, but then I feel uncomfortable like people are judging me. But when I dress like a woman, I feel uncomfortable because it doesn’t feel like me, and I think people are judging me because I don’t look pretty enough.

    All this to say, I have NO idea how to dress. Can’t I just be invisible?

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  7. Lesboi

    So far I can wear men’s clothes off the rack pretty well, though they’re not perfect. I’m not used to clothes fitting perfectly so it doesn’t bother me much. I don’t really like long sleeves so I always roll them up anyway. Men’s shoes are a challenge because I wear about a 6 or 6.5, sometimes a 7 and that’s hard to find. I’m curious if anyone has tried any of the butch tailors that are out there now like mentioned in this article. http://transguys.com/style/custom-tailors. Most of them mention custom suits but I think several also do custom shirts.

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