Which Side Are You On?

David Bowie in a man's dress, 1971

David Bowie in a man’s dress, 1971

David Bowie said it best “You must understand that it’s not a woman’s. It is a man’s dress.” If a dress is made for a man, or bought by a man, it becomes his. He owns it. The dress has no gender; the person wearing it does.

There was a cold snap and I broke out my favorite flannel shirt. It is a classic L.L. Bean, a Black Watch Plaid, in a women’s large. It used to look really good on me, before I lost weight. Now it is super baggy. I can still wear it, but I’m hesitant. It buttons to the left (the girl’s side).

I’m struggling with this. My weight is down from 175 lbs. to 140 lbs., but my height is still five foot four. My eyes have not adjusted. I can only see how much weight I’ve lost when I try to wear my old clothes. I’ve downsized my jeans several times and replaced a few worn out T-shirts. My button-down shirts are between two and five years old. They are between big and too big.

I stopped buying dress shirts because I knew I was going to stop working. Then I went on a self-imposed flannel hiatus because I have slew of old flannel shirts. It didn’t last. Then I decided to completely stop shopping for shirts because I want to wait until after I have top surgery. If I need to shop, I will stick to sneakers and hiking shoes.

It is almost impossible for me to buy a women’s shirt off the rack. I’m petite (I hate that word) and I won’t touch anything that has darts, princess seams, funny collars, or odd plackets. I’ll wear clothing made for women that looks like it is made for men. There isn’t much out there. It is also almost impossible for me to buy a men’s shirt off the rack. I like the styles, but the sleeves end below my fingertips, the body is too long, and if the chest fits it doesn’t close over the hips (and if the hips fit it is too big everywhere else).

I have a half-dozen fabulous custom-made dress shirts from CEGO shirtmakers. They were perfect when I weighed 165 lbs. The neck fits, the sleeves are the right length, the body is the right length, they fit over my hips, and they button to the right. They are too big, and I don’t wear them anymore.

I think of them as men’s shirts, but since they were custom-made for me, maybe I should think of them as butch/transgender shirts. I may be an idiot, but I can’t stand to think of them as women’s shirts.

I also have a half-dozen custom (women’s) classic Oxford cloth shirts that I bought at Brooks Brothers when I was 155 lbs. They still look good, even though they are a little baggy. Except that they button the wrong way.

It is my quandary, to wear them or to give them away. Donna claims no one else notices which side my shirts button on. And, she reminds me, no matter which shirt I am wearing, I read as masculine, not male.

Some guys are oblivious to fashion and some pay attention to what other guys are wearing. They’ll snicker if they see a guy wearing a brown belt with black shoes, or wearing blue socks with a black suit. I don’t want to be one of those guys. GSElevator writes about this in How To Dress The Part On Wall Street. He’d notice the buttons. Do I care about him? Am I so shallow that seven buttons have me in a swivet?

Women may wear men’s clothes, but men do not wear women’s. There are boyfriend cardigans and boyfriend jeans for women, but no girlfriend jeans for men.

It turns out that this is not entirely true. Levi’s marketed an “ex-girlfriend jean” for men. A tight punk rocker cut. Most guys don’t borrow their ex-girlfriend’s clothes (and why the ex, instead of just girlfriend?). For the record, over the years, Donna has purloined several of my T’s and flannel shirts. I have never, ever, ever, worn a piece of her clothing.

I have a fantasy that men’s shirts will fit better after I have top surgery. Logically, I know that the discrepancy between my chest and my hips will still make it difficult for me to buy a shirt. If I want a shirt that buttons to the right and fits, I will have to go back to CEGO.

A survey of my closet turned up over twenty flannel shirts. Only two (both L.L. Bean mediums purchased last year during the hiatus) fit properly, and they both button on the left. I will need to look back at David Bowie and think of them as butch/transgender shirts. Because that is who I am.

Note: After an extensive investigation it was discovered that GSELEVATOR never worked at Goldman Sachs. The New York Times expose of the Tweeter is here. Some people take Twitter way too seriously.

35 thoughts on “Which Side Are You On?

  1. anexactinglife

    I wear shirts, as opposed to blouses or tops. Because of my size (small on top and wider hips), I look for plain women’s shirts without darts, but I can’t wear men’s shirts untucked because (as you said), if they fit on top, they gap at the bottom. Sounds like custom men’s shirts would be the answer! I don’t mind which way a shirt buttons, but I can understand why others do – there is a desire for an authentic experience, without telltale signs of being “someone else.” I have a pair of cufflinks, BTW, that I can wear with a couple of shirts – love them!

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    1. Jamie Ray Post author

      I usually roll my sleeves up unless I am wearing a sweater, but I have one pair of monogrammed cuff-links that I inherited from my Dad. I keep them even though I don’t have a shirt to wear them with. When I get around to ordering my next set of custom shirts (you would be appalled at the price because they run over $100 US, but they last until you get tired of them or outgrow them), I should get one shirt made to take cuff links.

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    1. Jamie Ray Post author

      Everyone has their own things that annoy them – buttons and having the right hair cut are mine. I find it odd that manufacturers distinguish between the two sides (there are historical reasons for it but they are outmoded); whether they think a cisgender women would feel uncomfortable if it buttoned to the right.

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  2. gok9go

    I’ve worn men’s shirts for years. And, because I weighed more and had a chest, my shirts were always baggy. That meant that the sleeves were always a bit long, but I never let that bother me. I hid in baggy men’s clothes for years, even before I picked up weight. I’ve been told that I did a good job of hiding my 42-DDs beneath my baggy clothes.

    Jamie, like you I stopped buying shirts prior to surgery. I had no clue what size I would be. Now, post-surgery, I am still trying to get a handle on size. I expected to go from XL to L, but one company surprised me and I bought a size M. Weird. I put on my XL t-shirts and swim in them. I imagine if I put on my XL flannel or Oxford-cloth shirts, I would swim in them as well. But they’re nice and fairly new, so I might still wear them. Not sure. I have a decent wardrobe of shirts that are L’s, so hopefully those will fit. We will see when the weather changes.

    Here’s the big thing I noticed: I know that my shirts are big now, but I have a hard time getting them in a size that is more fitting. I spent so many years hiding my chest that I am used to baggy. Now that I don’t need to hide what never belonged on me in the first place, I need to get used to the idea that shirts should fit. That’s hard to wrap my head around. I have pecs that can be seen beneath my shirt, and I wonder what folks think if I wear a more fitted t-shirt or polo. This is another thing I need to get over–it’s not about what others see; rather, it’s about how I feel.

    I joked before top surgery that the only piece of women’s clothing I wore was a bra. Now I wear none–from head to toe, my clothes are men’s. I learned a long time ago not to be apologetic for that fact. It’s about my comfort. Honestly, buttoning my shirt the wrong way (for me, that would be for a women’s shirt) would feel wrong, but that’s because I have worn men’s shirts for so long. As Muddy River Muse says, it’s you who knows which side your shirt buttons from–be true to you in the best way possible.

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    1. Akiva

      I thought I was going to wear smaller shirts after top surgery, but I (generally) don’t—I still have more hips/curves than I am comfortable showing. It’s been hurtful, not gonna lie.

      I also relate about showing pec (and nipple). It was alittle nervewracking at the start, but I’m getting over it. I still worry sometimes that I look like a stereotypical hairy-legged girl who doesn’t wear a bra. Checking out cis men’s chests has helped with this—a lot of them have as much up there as me, and they’re shameless.

      I’m exactly 6 months post op today (I just realized that, huh!), which isn’t that long in the scheme of things, so I hope I’ll continue to get more comfortable with the social aspect of my chest as time goes on.

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      1. gok9go

        Congrats on being 6 months post op today! I am a bit over 7 weeks now–amazing. I have noticed cis men’s chests and decided the same thing you have. I also figured out that mine looks the same now, so folks can deal with it (and once I gt back to lifting they can deal with more pecs). The first time I walked around campus and saw a cis man’s chest, I felt no jealousy–I felt relief that I finally have *my* chest.

        I’m with you on the more hips/curves than I am comfortable with. But, I have noticed that I am not dysphoric about it like I was with my chest. It may become an issue when/if I want to wear a suit or tux and want to look sleek, but for now it’s okay. And, as you mentioned about men’s chests, some guys have more “booty” than I do, so hopefully I can get over it.

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      2. Jamie Ray Post author

        I look like a short haired, hairy legged, queer person as it is, so if I look like one with Moobs I’ll just have to deal with it. Don’t you find it kind of strange to be checking out cisgender men to see what their chests look like (I also do this with short good looking cisgenger guys to see what they are wearing)? After years of just looking at women and dogs, sizing up guys is kind of strange.

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    2. Jamie Ray Post author

      It is interesting how everyone’s experience is slightly different. I’m going to have my surgery in December so that I’ll have the winter to come to grips with pecs and nipples.

      Since I started binding on a regular basis, my men’s shirts fit better, and I think my hips are still going to be the determining factor in my size.

      I’m not exactly a hipster, and it annoys me that men’s styling has gone to the slim fit, just when I am planning to shop for shirts (another reason to go custom because I can ask for exactly what I want although I do have to pay for it).

      I have no problem wearing men’s jeans (eventually I find a cut/brand that works), and I do not intend to ever wear dress slacks again except for funerals, weddings, and bar/bat mitzvahs. I have under grown my old dress slacks, and trying to get new ones could be another obsession.

      Being true to oneself is a PIA.

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  3. Charlie Nicholas

    Losing weight and my hip-waist ratio is more different the I thought. And my boobs are larger than I remembered (I once lost all this weight before but wore sports bras back then). I will never go back to women’s clothes because they cause me that much dysphoria. I hate the fact that I may never perform en drag if given the chance 😦

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    1. Jamie Ray Post author

      When I was heavier I also did not notice my chest as much because the fat camouflaged it. Dysphoria is serious – I have panic attacks when I wear “real” women’s clothes. I still wear baggy stuff to square out the curves.

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  4. krisalex333

    As I re-read your post, I made a mental check each time I shouted “YES!” (I was going to write ‘exclaim,’ but find it too effeminate a word. Your post ended up tick-infested (I hope you don’t end up with tick bite fever 🙂 ). I just have the buttons on my shirt cuffs moved a bit tighter, so they don’t end up below my fingertips. Geez, compared to me, you are tall. I’m barely 5’1″+ and shrinking (note the very important +). I often wish I could have dungarees made from the cut-offs from my jeans – pooch would look so cute in them. (Wait – is ‘cute’ a word men use??)

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    1. Jamie Ray Post author

      I wasn’t sure if I was the only one who obsessed over stuff like this or not (I’m not proud about it but someone needs to write about it for posterity). But clearly it resonates with people like us.

      I wish I had learned how to sew (talk about doing girly things) so that I could take things in and hem them. The best I can do is to sew on a button.

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    1. Jamie Ray Post author

      What you say is true, but dysphoria is insidious and hard to get over. When you grow up hating how you look, a part of it stays with you forever (which is why I write).

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  5. Pixie

    I plan on switching the buttons on a few of my more comfortable shirts that button the female way. Have not done so recently, not had time to, but it really is not that hard to do. Having a sewing machine helps, but with patience it is possible to sew up button holes by hand. I suggest (for myself too!) practice on scraps of cloth first. The key for a good buttonhole is very sharp scissors to leave a clean edge.

    I don’t worry about anyone else noticing the buttons the wrong way, no strangers ever read me as male anyways. But it is triggering enough for me personally having to do up the buttons that I don’t wear any of those shirts.

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    1. Jamie Ray Post author

      Hi Pixie-
      Thanks for your comments on the buttons. I never learned to sew well (too girly) – I only learned to cook because I managed to convince myself that it was masculine (i.e. I was a chef not a housewife). I’m afraid that it would take me way too long to figure out how to do the button holes, and I am not patient with fixing things or crafts (I am patient when I cook, but the food is doing it’s own thing compared to fabric and needles).

      Donna, my partner, said basically the same thing – how I am read had nothing to do with which side of the shirt my buttons are on. It is a nuance that most people will not get. It is all about me and how I think about myself.

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      1. Pixie

        I’m gay, so I was mostly able to re-define the “girly” things I like in those terms. Like sewing. Which I actually do a lot of, like cloth dolls. Of course all my dolls are boys, even the ones in shiny dresses… 🙂

        Unfortunately, that seems to have made me dangerously triggered by genital dysphoria. Because of course, gay guys are all about dicks…

        See if you can find a tailor/seamstress in your area. It should be just a matter of 15 min or so for them to fix the buttons for you, it really is that simple. You could just say that it annoys you to have shirts buttoning both ways, don’t need to say more than that if you don’t want to.

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      2. Jamie Ray Post author

        Thanks for the suggestion. I never thought of doing that. The shirtmaker that I went to for the custom made might be able to do them (I haven’t found a tailor that I like and feel comfortable asking to do gender stuff – but the shirt guy completely gets it).

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      3. Pixie

        On second thought, you could also look for a group of people who sew/design/alter clothing as a hobby. Furries, SCA/reenactment people, theater people, any of them probably would happily help out on such a small task. I’d offer to do it myself if I was nearby. 🙂

        My perspective is: any small things I can do to make my day less triggering is worth the effort because there is so much that I *can’t* do anything about. Every little bit helps a little bit, even if it is just because I am doing *something* about it. Doesn’t matter that it is just my perception of myself, it still matters.

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  6. Lesboi

    I’ve just started to wear button up shirts again. I used to wear them a lot but as I got heavier over the years I felt like they made me hyper aware of my chest so I switched over to polos. I probably have 20 polos of varying colors and wear them most days. My button ups are mostly short sleeved due to the fact that men’s long sleeves are too long for my 5’2″ frame. Plus, I have never really liked long sleeves to begin with. I always end up rolling up the sleeves and they still aggravate me. Interestingly, my brother is the same way about his shirts. Back before I knew I was trans I switched over to buying men’s polos and button ups because they were cheaper, better made and didn’t shrink up after one washing to end up being unwearable. I’ve never looked back, and really don’t pay any attention to which side my buttons are on. I have a few nice women’s dress shirts I bought from Land’s End that fit nicely and I feel good wearing. For me, with my current chest, those shirts just make more sense right now. I’m guessing once I have top surgery that will change, but don’t know how at this point. I like David Bowie’s philosophy about clothes. Once I buy a piece of clothing I no longer think of it as men’s or women’s but as mine. I mix and match genders when necessary and really don’t care about it at all.

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    1. Jamie Ray Post author

      I’m going to work on re-framing all my clothes as butch/transgender clothes (including my boxer briefs). Its interesting because I stopped wearing polos before I started binding because they were too clingy and made me self-conscious about my chest. I’ve worn button-down collar shirts since I got out of college (when they were briefly in style for women – but I never wore the floppy tie with them – a la “dress for success”), and I’ve always felt comfortable in them.

      The custom shirts were a real indulgence, but I allow myself to get them because it is so hard to find what I like, and liberating in an odd sense to be able to buy exactly what I want and have it fit right.

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      1. Lesboi

        Actually, after giving this some more thought, I think the real reason I stopped wearing my beloved button up shirts is because I got fat around my waist and tucking them in was making me uncomfortable. Possibly, the tucking pulled down on my now larger chest and that is what made me think it was my breasts that were the problem. I guess it’s all a package at this point as I’m not comfortable with my belly or my boobs. I tend to wear shirts that I don’t have to tuck and I guess that’s why polos and t-shirts are my go-to now. Sometimes I’ll wear a large button up or a hoodie over my t-shirt in the winter months if I really want to hide my boobs. I haven’t found a binder yet that I’m comfortable wearing so I just have to suck it up and try to forget they’re there as much as possible.

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      2. Jamie Ray Post author

        I’m not into pain either, and I found it hard to find a binder I could wear as comfortably as a sports bra. My go to binder is the Air M Velcro Binder from Les Love Boat in Taiwan. It is cool enough to wear, and adjustable (you just have to measure right the first time when you order). I also have a V neck binder from them that is a good but has thicker fabric in the back, but looks better under a polo or shirt that is open at the neck (the Air M looks fine under a crew neck). I’m a 38C, so don’t be put off by the very thin models on their website. For me they worked better than Underworks.

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  7. Mxtrmeike13

    “Women may wear men’s clothes, but men do not wear women’s. There are boyfriend cardigans and boyfriend jeans for women, but no girlfriend jeans for men.”

    This was a problem I had for a while…although I only ever wore men’s clothing, that binary way of thinking about gender and clothing used to get the better of me. Now I’m at a point where I’m starting to see clothing like I see myself — gender neutral — and choose my clothes and style based off of how I want to present myself, which is on a sliding scale from neutral to masculine.

    If you don’t see don’t see yourself as a man, then the argument falls apart. Example: I see myself as a person. A neutrally gendered person, if you will, but simply as a person. Therefore, as a person, I’m entitled to wear clothing. Men’s clothing, women’s clothing, boy’s clothing…it’s all just clothes, and if it fits and makes me look how I want to look, that’s all that matters.

    Good luck with your shirt/clothing problems! (Also, I feel you on the shirt sizing issue — I only used to be able to buy dress shirts from Express that were extra slim-fit and extra small.)

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    1. Jamie Ray Post author

      The whole “how I see myself” thing is complicated. I don’t see myself as a man, more as a boy, in the kind of pre-pubescent generic kid kind of way. My head is non-binary – I don’t really want to become socialized as a man – or a woman for that matter. Like Popeye said “I am what I am.”

      However, since I spent such a long time refusing to be a girl, it is hard to break the “if it is for women or girls then it is bad” thought process when it comes to clothing or accessories. I have a hard time allowing myself to play around with it (e.g. wear pink) – my tendency is to be rigid. I’m just happy that I live in a time and place where I can play around with it and talk/write about it.

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  8. micah

    I bought some “vagina” pants in Canada. I call them that because they scream vagina! right? No, just kidding… they are from the women’s section, which is rare for me now, but they fit great. They are also my “nurse” pants because they are turquoise and look like scrubs.

    Any clothing still in our closet from my girl days belongs to my partner. Mind you, it is now “vintage.” When her coworker compliments her shirts, I think, would it be too weird to tell her it used to belong to your boyfriend?

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    1. Jamie Ray Post author

      I have two pairs of those “V” pants (black and brown) that are reserved for situations where I can not (should not) wear jeans or cords – funerals and bar/bat mitzvahs. The fly points in the wrong direction which is irritating. They are a little too big, and eventually will get replaced with something else. I can’t imagine wearing turquoise blue pants (the closest I come are bright blue camouflage boxer briefs but no one else gets to see them) – I know you are into bright colors.

      Donna has some of my old flannel (all the bright ones eventually migrate to her) and she uses my old dress shirts to paint in (she goes to an open studio at the Art Student’s League). She gets flummoxed trying to explain who I am, because everyone assumes she is straight and expects me to be a cisgendered guy. We are a complicated pair.

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  9. txbridgefarmer

    Maybe I’m wired differently. I’ve always worn “men’s” clothing. Shirts, pants, briefs, etc. and never thought twice about it.
    For me, it is almost as if I’m trying to draw even more attention to myself if I were to dress in women’s clothing. I’m obviously butch. Short hair, stocky build, no make up, etc. To put on a “blouse” would make me feel awkward. Almost as if I were cross dressing.
    I do hate that men’s shirts have to be tailored in order to be flattering, but I hate looking in the mirror and thinking, “I almost look good!”

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    1. Jamie Ray Post author

      You are lucky to have a good tailor that you trust to take in your shirts. I never done the “blouse” thing, but I’ve had difficultly because of my height finding mens shirts that fit (pants are easier because they can be shortened and taken in at the back).
      I’ve always preferred to cross dress (long history of us butch cross-dressers), and refused to take jobs that would not have allowed for it.

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  10. The Little Butch That Could (TLBTC)

    And that is why I shop in the boys section. . . towards the “husky” end of the scale due to my hips but as long as the shirt fits over the boobs, I’m usually good to go. Cheers.

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    1. Jamie Ray Post author

      I’m a little too big for the boys department (haven’t tried Huskies) – but I do look at good looking short cis guys to see what they are wearing. I might make it into boys after top surgery. Time will tell.

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  11. Pingback: The Perpetual Search for the Perfect Shirt | A Boy and Her Dog

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