You’re Ugly and Your Mother Dresses You Funny

I am finally coming out of the closet. Not that one. I’ve been out of that one since I was eighteen. I’m talking about my clothes closet. My wardrobe. Interesting word “wardrobe,” meaning both a piece of furniture that holds clothing and the outfits themselves. Well mine feels like a prison and I can’t stand it anymore. I keep brushing up against hastily purchased items—a silver blouse, some velvet pants… I think I just tripped over a pair of sensible pumps. Are those really mine? How did this happen?

I blame my mother. That’s fair, right? I first saw myself reflected in my mother’s eyes; a blurry, girl-shaped image filtered through her vision of what I was to become. Parents do this. They create a mental picture of who their adult children will be. The templates we daughters are expected to conform to are mostly the same. Is she kind? Check. Caring? Check. Sugar and spice and everything nice? Check, check, check. So far so good. And my template was not too constrictive. My mother is sporty and so am I. My mother likes to dress in casual clothes most of the time. Awesome! Me too! My mother is straight and has been married to my father since 1966. Er… uh… hmm…. (If we don’t draw attention to that one, maybe no one will notice.) When my mother dresses up she wears skirts and dresses and heels and make-up and sometimes even curls her hair! What?!! I think we have a problem….

I don’t see myself as my mother sees me. For her, and for most of our culture, the clothing part is the easy part. When girls dress up they wear skirts and dresses and (apparently) they like it. Styles vary, but the gender signifiers of the clothing are quite clear. When I see myself reflected in the mirror in an outfit like that, it makes me queasy and anxious because the image I see reflected doesn’t match the way I feel. And it’s not that I don’t feel female, but I have never felt feminine. This has been a source of frustration and despair for my mother and for me.

There were times growing up when I donned some fancy duds, looked in the mirror and liked what I saw. But the clothes I was wearing on those occasions were not the clothes my mother wanted me to wear to large family gatherings. I wanted to dress like my dad. You see, when I was a little girl, my dad taught me how to tie a necktie. He taught my brother and me both how to tie his favorite knot, the Half Windsor, and I loved to practice it. My dad had so many great and colorful ties to choose from. (It was the 70s after all.) He also had a fantastic hat collection: fedoras, bowlers, Irish caps. I loved dressing up like him then surprising myself in the mirror, catching a glimpse of the boyish spirit that lurked inside.

As I grew a bit older, my necktie tying skills came in handy for certain events, like Casino Night in high school. My friends would wear very becoming, tight fitting flapper dresses with rows of swinging fringe and knotted ropes of fake pearls. I would get my dad’s white tuxedo jacket out of its thin plastic dry cleaning bag, grab his fedora from the top shelf and knot up a stylish tie. I swaggered in that outfit.

And there was the time when I was working as a lifeguard at Girl Guide camp and the staff re-enacted Prince Andrew and Fergie’s wedding. I was Prince Edward in a borrowed military uniform jacket, shirt, hat and tie. (Our “Prince Andrew” came out a few years later, around the same time I did. Henh.) I couldn’t stop looking at myself in the mirror. I felt so good. So sharp.

But those were costumes, right? That wasn’t how I was supposed to dress. For celebrations, girls wore fancy girly clothes, and might, (oh please, please!) get away with dress pants and a blouse. And I accepted this. Resigned myself to it, I suppose. I saw no alternative on television, in the movies, in the myriad images of “female” which had swirled around me like amniotic fluid since my egress from the actual womb.

So I had a wardrobe of acceptable (to me and to my mother and therefore the rest of society) unisex clothing: pants and shirts loose enough to disguise any overtly feminine features, sweaters and sport-specific clothing, outdoor wear. And a few grudgingly purchased “good” clothes: a skirt,a few blouses, two pairs of dress pants, NO DRESSES, one pair of dusty heels. At every wedding or shower or royal ball I looked like a secretary who had come straight from work. Fully aware of my inadequate wardrobe, I wore my discomfort like a puss-filled zit. But it didn’t stop people from complimenting me on how nice I looked. Applauding my effort. (“All she needs is a little encouragement.”)

I’ll tell you this right now, I’m cheap. Anytime I have to spend money on something I don’t like, I get very grumpy. I can still feel the pain of every penny spent on an outfit I purchased because I thought I had to. Why is it that a woman is expected to show up in a totally new outfit to every social event when a man can get by for years with a couple of suits?

Ranting about this to a friend of mine a few years ago she said, “Why don’t you get yourself a nice tailored suit?” And to be honest I’d never really considered it. I think at the time I eschewed the idea as too expensive and over the top. But somewhere inside me the idea stuck.

My journey out of the sartorial doldrums began two years ago with a necktie. Faced with yet another Xmas party where all the women had bought new dresses, “even fancier than last year’s”, I decided to do something different. It was a party full of actors and musicians, so I felt freer to experiment. I did it. I crossed the aisle. I headed to the men’s formal section and found a purple and cream tie which I paired with a shirt with French cuffs. Success! My tie was drooled over by men and women alike that night and I felt good. I got my Casino Night swagger back. This time I believed the compliments.

I later matched the tie with a simple black v-neck sweater and wore it to a work conference. Again the compliments. Again the swagger.

And finally, last year, I bought a suit. An off-white vest and pants. It was from the women’s section at H&M and it felt like the perfect mix of fit and line. And I bought a vintage tie. Actually, I had bought the tie first. This was becoming a pattern for me. I found this great tie and knew I needed the right thing to wear it with. I bought the suit to match the tie and when I put them on and looked in the mirror I felt good. A hint of feminine mixed in with the masculine. I felt dapper and suave.

I began to search through vintage stores to find ties I liked. Early 1960s skinny ones mainly. And my wardrobe began to change. I began to enjoy matching my ties with dress shirts and argyle sweater vests or slim fitting cardigans. And the more I dressed “like a boy” the more the girls began to notice. All the girls. Even straight girls. It was amazing. They looked at me and smiled in this very interesting way like they were attracted but surprised at the same time. It was so hot. I gained a confidence I had never before possessed. I felt sexy. I had never, ever felt sexy.

Now when I look in the mirror, dressed in my finest threads, I like what I see. And the more confidence I gain, the easier it is to ignore the shadow of disapproval I still see reflected on my mother’s face. It took me a long time to realize that I was free to make this choice. To choose my happiness over someone elses. To show on the outside what I feel on the inside. I am 41 years old and I’m not going to let my mother dress me anymore.


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  • Great Article! Confidence is probably the sexiest thing anyone can wear.

    And suddenly I have zz top in my head…
    cause everyone is crazy ’bout a sharp dressed woman!

  • I’m trying to come up something witty to say, but all I can come up with is WORD.

    I’m a college student who has been passive-aggressively butting heads with my mother about how I dress for years–recently, it’s come to a head with a couple of weddings in the family. I was so touched that my very sweet sister-in-law offered to work with me to find a bridesmaid outfit I felt comfortable in that I decided to go with the matching dress–I treated it as a part in a play, which it kind of is.

    This “concession” has only spurred my mother on–at another wedding, in which I was a guest, I was abundantly clear that a dress was not an option; it took my mother a few months to take me seriously. (GAH!) It’s a lot of give and take (she bought me a lovely tuxedo, but she’s constantly harping on how I wear my breasts).

    But you are so right–at some point, you need to just ignore that disapproval in their eyes. What’s more important, the swagger that helps me network or pleasing my mother’s half-false image of me? Everyone is so much more attractive when they’re comfortable in their own skin; sacrificing all that beauty for gender standards is awful.

    Thank you for writing this.

  • Oh man, thank you so much for this article. The is what I am having the hardest time with right now. My family is accepting of me being gay, except if I “act gay.” Then it gets all sorts of uncomfortable, like when I cross the gender boundaries of clothing, which I have been doing since I was a child.

    This article really helped me.

  • Wow this article is spot on! I always knew that I didn’t like the “girly” direction that society and my mother always seemed to expect me to take. Most people look at other women to find examples that they like and then they work it out from there, who was I supposed to look at? I always felt horribly uncomfortable in what I was wearing. I always relented to wearing something, I never wore anything I actually liked. The clothes were all basic jeans, t-shirts and hoodies, which was acceptable according to the norm and my parents. Years wasted on bad style because I hated the direction I was pushed towards, but didn’t know what other direction I could go in. It destroyed my self-esteem, I felt like I was lying to myself and to others. I finally stopped listening to my mother and I stopped giving a crap about the “norm”, best thing I’ve ever done. I can say that my mother wasn’t thrilled, we’ve had a couple of arguments when it comes to style. She seems to think that I’m “limiting myself”, I on the other hand feel like I’m finally free.

  • Titus! You are so handsome!
    Admiring the Dapper Q in/on you… but unlike the straight girls, I’m not surprised… I see you, I recognize you, I smile knowingly, I tingle…
    Thank you brave butch for making my world a happy place!
    Love a femme friend

  • I really LOVE this article and the responses it has generated.

    This past weekend has shown me I may never be too old to feel the pain of these issue, especially when in comes to family.

    Have been very struck by the responses, especially D who said, “My family is accepting of me being gay, except if I “act gay.”

    We have so much work to do, as a community and as individuals, to walk through all this to make the way clear for those who follow. Titus, I heartily welcome the addition of your swaggering and passionate articulation. More please!

  • Love this! Thank you, Titus for this insightful and well-written tome.
    I, myself, lean more toward the artsy/rocker….(do I dare even say the name?) “Shane” look….but since I work in a professional atmosphere…I have to “rock” a little less…

    Anyway, I “get” the whole…fine to “be gay”…just don’t “look” it…

    Or, as my Mom said, “Nobody has to know WHAT you are…” To which I reply, “If no one knows WHO/WHAT I am….how’m I gonna find my lady?”

    Erm…carry on, DapperQ’s!

  • I hate shopping for clothes, because generally it’s really hard for me to find something that I feel comfortable in. So I tend to have a very limited wardrobe.
    But I had the greatest day today; my best dude friend and I happened to be at the store, and walked past the boys clothing section when I remarked that I liked the plaid shirts (I love plaid shirts), so he said “ok”, and we went over there, and I picked some out and bought them. Not only does it appear that I fit shirts for pre-teen boys, but the quality is far greater, and they are about 1/4 the price I pay for womens plaid shirts. I’m just not going to tell my mom that they’re boys shirts… heh heh heh
    It was the first time I haven’t felt horribly awkward while shopping. Just thought I’d share 🙂

  • Thank you so much for this wonderful piece and congratulations on finding your swag! I am super feminine, yet this article was inspirational to me. Here’s why. Growing up, my family allowed me to dress as I wanted. I’ve ALWAYS been drawn to lace, pumps, glitter, skirts, anything “girlie”. I would even wear patent leather flats to my physical education classes in elementary school. When my P.E. instructor forced me to wear sneakers, I would look down at them and cry “but they’re so ugly”.

    I’ve always been a fashionista and suppose I’ve been lucky to feel comfortable in clothes that are considered “appropriate” for women (cut me a break here, I’m a bi-racial lesbian who grew up poor in Albuquerque – it was good to have at least one break). However, lately, the trend is to look anything BUT traditional (to the point where looking out of fashion is the fashion, but that’s another article). I’ve tried to squeeze into the “Urban Outfitters” ensembles. But, no matter how hard I try, I will always be more “Club Monaco” (I do the menswear thing with knee-high boots with 7 inch heels). So, thank you! Thank you for just reaffirming that what feels right for us is usually what works for us. We have the most style and self confidence that others are drawn to when we are true to ourselves. I hope to see more of your writing!

  • Way to be dapper! Excellent article! Like you said, it is all about feeling good, and enjoying what you are wearing.

    Rock on.

  • At age 10 or so I asked my mother why, if women were men’s equals now (again, I was 10), they still wore skirts and high heels and makeup. It didn’t occur to me that it might be because they *wanted* to.

    Now, quite a few years later, I know that many women like to dress like that, but that I prefer men’s clothes. I still haven’t quite persuaded myself that this is okay, but once I do I hope to be confident enough to swagger a bit, too.

    Thanks for writing this! I’ll tweet this to get more people to read it.

  • Just found the site and loving looking back through the posts. You’re totally right about the confidence thing. I’ve worn guys clothes my adult life (now 45) and I still get the odd look, but, I’m only aware of it when friends point it out, because I just don’t notice.

    Friends and work colleagues totally except who I am (including the rather uncool habit of smoking a pipe – I’m a bit of a baccy geek). The funny thing is that if it’s ever suggested I wear a dress or make-up the same friends and acquaintances shriek with horror. Sometimes I think people are just comfy with what they’re used to, and they’re used to me in masculine clothes.

    Even when I was doing my nursing training, and the college required that I purchase a uniform from a supplier that would only sell me the women’s blouse for prac,I just sent a friend in with a list of measurements and pretended it was for a male student unable to get there for a fitting (bit of fibbing, but, I was ticked off). Nursing School never made a comment about the guy’s shirt once I rocked up wearing it.

    I would rather face the critics in a 7-fold silk tie than gain approval in a frock. I love dresses and skirts on other women (mind you, I love suits and ties on other women too), but I would feel skeevy and dorky in one myself. It is about feeling sexy and confident, irrespective of your type of dress. As for whether my mother likes my clothes 🙂 That stopped being of any importance when she stopped paying for them. Mind you, I do feel a little sorry for my neice when I hear her having to explain, “That’s not a boy, that’s my favourite aunt”. Luckily she’s a class act and doesn’t bat an eye-lid, bless her!

  • Thank you all so much for the amazing comments and reflections. I am making some interesting discoveries about myself through my commitment to style, and no one is more surprised than I to find these things linked. I hope my stories continue to resonate. Stay tuned!

  • I can relate so much to what you just wrote. Ok Im 19, but since I was little both my parents thought dresses and skirts and all these other female looking clothes and accessories would suit me how rong they were. I love mens clothes, If I go anywhere near a female section I get dirty looks as if Im no supposed to be ther. I hate shopping altogether with my famil due to the fact People kept thinking I was a guy because of how I dressed. I want to change my style so people recognise me as a girl I am so tired of people thinking I am a dude, I feel embarrsed if it happens when Im in company of my family.

  • Confidence is sexy. And it’s wonderful that as adults, our mothers don’t buy our clothes anymore. But they will comment on everything we wear…we gotta love them 🙂

  • Love this article! Truly inspirational: it’s all about creating an empowering style that enhances your essential energy. I’m a color and wardrobe consultant – and a femme. No matter how we define ourselves, many women struggle with creating a style & look that feels authentic. It’s an evolving process that requires courage and confidence.

    Thanks for sharing your story! An important reminder!

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