This is the story about the black dress that hung in my closet as a kid. It belonged to my mom and was the garment that kicked off my interest in dresses and skirts. As I recall, the dress was primarily made of cotton, had spaghetti straps and would have come down to mid-thigh if my mom had worn it. Oddly enough, I can’t recall ever having seen her wear it or it ever leaving my closet except for when I pulled it out.
When I say that it would have come down to mid-thigh, that is just conjecture on my part because the hem always ended up well past my knees when I put it on as a not-fully-grown preteen and teenager. By that time, the dress had been in my closet for years and I had seen it every day. Naturally, curiosity got the better of me and I eventually pulled it out to look at it.
At first, I would just spread it out on the floor or my bed and study it. I badly wanted to try it on and see what it felt like to wear a dress, but I was scared. At the time, I didn’t know why or what I was afraid of, but looking back on it with the gift of hindsight, I can say I was afraid of what I thought it would mean if I wore it and liked it.
As an inexperienced preteen, I thought that even just my interest in trying on the dress meant I might be gay and that if I tried it on and liked it, it would be confirmation of that. Unfortunately, it was a time when being gay as a young male was still something to be afraid of. While society in the part of the US I grew up in was becoming more tolerant, gay or “feminine” boys were still relentlessly bullied at school instilling a strong fear in them of falling into this category.
The concept of transgenderism wasn’t on my radar at all yet, so that wasn’t even a consideration. It would only become a topic later in my life, but I’ll write about that in another post.
Pulling the dress out, looking at it, touching it, feeling it, and resisting the temptation to put it on became an almost daily ritual that went on for at least a year. Then one day, I finally gave in and put it on. I can’t remember whether it was after school or on the weekend, but I do know that the fact that I was home alone played a big role in my decision to finally try it on.
I pulled the dress out, looked at it spread out on my bed, then rapidly stripped down to my underwear. I recall being so nervous that I was shaking and sweaty which in hindsight is ridiculous, but what I was about to do was a big deal to me in that moment. I then grabbed the dress and slipped it over my head.
The only way to accurately describe the feeling of finally wearing it is to say that it felt euphoric. I was nervous and afraid, but I somehow felt whole in a way I hadn’t before. It was as though a missing piece of me had finally been found and slid into place. From a distance of decades, that sounds rather absurd and melodramatic, but I remember the feeling distinctly. Even to this day, I still experience a much tamer version of it when putting on a skirt, dress or heels.
That day marked the beginning of a new, life-long passion for gender-non-conformity. At first, I would wear the dress only when I was home alone, but since we were a family of five, that wasn’t often enough for me. Eventually, I got brave enough to put it on and wear it even when other people were home, but only in my room which was pretty isolated in the basement.
This had the side effect that I began to withdraw into my room more and more which my parents just attributed to me being a teenager. Little did they know it was so that I could wear a dress. Of course, a lot of teenagers use the private space of their bedrooms to discover themselves and that is exactly what I was doing.
As with most things teenagers try to hide from their parents, there was a time when my mom very nearly caught me. I was sitting in my room playing PlayStation (the original!) while wearing the dress. It was winter and my room was somewhat cold, so I had a long sleeve shirt on underneath as well as a blanket over me which was fortunate. My room didn’t have a door, but it was in the basement which meant I could hear her coming down the stairs. I obviously didn’t have time to change, so I just quickly pulled my arms out of the dress’s spaghetti straps and pulled the blanket up to almost my neck so that it was concealed. I then kept playing my game as nonchalantly as I could muster.
Obviously, I was quite nervous but fortunately, nothing happened. My mom did notice the blanket pulled way up and the fact that I was acting a little strangely, so she asked if I was feeling alright. I assured her I was fine and that was the end of it. I doubt she ever suspected that I was wearing her dress under the blanket.
Years later after I had told her about my interest in skirts and even worn them in front of her, I told her I used to wear the black dress that she kept in my closet when I was alone in my room. She couldn’t even remember having one in my closet which explains why I never saw her wear it.
As a teenager, I frequently had friends over and we would spend time in my room and play video games for the most part. When I knew they were coming over, I wouldn’t specifically hide the dress as you might expect. Instead, I just left it hanging in its usual spot. No one noticed or asked, but if they had, I would have just told them a redacted version of the truth: it’s my mom’s and she’s storing it in my closet because hers is too full. None of them would ever have suspected that I actually wore it as often as possible.
I can confirm that because I am still good friends with my two best friends from school who came over all the time and I have since asked them. Neither one of them knew about the dress much less that I wore it. A fun twist is that one of them started to wear skirts too even though neither one of us knew about the other one doing it. It was only years later that we discovered we both had a common interest in gender-non-conformity. She later came out as transgender (MTF).
I don’t really know what happened to the dress unfortunately. When I moved out for college, I didn’t take it with me even though I missed it. I wasn’t about to have it in my dorm room which I had to share with another random guy and by the time I had a place with my own room, the dress had disappeared. I assume my mom took it back at some point and probably gave it away to Goodwill like she does with most of her old clothes.
That doesn’t mean I didn’t experiment in college once I had moved out of the dorms though. With what little money I had, I ordered myself a skater skirt with thigh highs (think typical femboy) that I wore every time I thought it was safe enough to. I still had roommates, but I did have my own room with a door I could lock. This went on for my entire college career until I packed up my things and moved to Germany to be with the woman I am now married to. I didn’t take the skirt with me and didn’t get another one until several years later.
It’s hard to say how much of an impact that black dress in my closet had on me and my current situation, but I can make a fairly confident guess that it was pretty significant. If it hadn’t been there, I may never have discovered the joys of clothing sold in the woman’s department. It started a real passion for it which is something that continues to this day.
Great story. What I love about it (besides having similar ish experiences) is how open and honest you are. This will help your wellbeing in unmeasurable ways.
When I first donned tights as a kid, I had the similar “everything’s right with the world” kind of experience. Seven year old hyperbole but now I realize tights are my security blanket. When I’m facing something difficult, they’re on. Wonder if that’s why superheroes super suits have tights too….
I wore tights as part of a play. You found a dress because your mom just needed space for something she knew she wouldn’t need often. Or at all it sounds. Seems so sad that she didn’t wear it.
We had similar almost getting caught experiences though I was actually caught. Several times. My parents never said much except tights are for girls. But I didn’t get yelled at or harshed upon like I’ve heard some have. So I was lucky.
I’m sure a psychologist could have a field day learning from how men take to the taboo that is wearing clothing traditionally associated with women. The concern about what it means loomed large in my head too. I remember getting seriously upset when I worried to my girlfriend (who knew) that it meant I was a transvestite. She didn’t think so. It was pre internet days so you didn’t have the chance to google that word and really understand. In fact I didn’t have the ability to check anything out. It was left to my own mind to determine what it meant to want to wear women’s stuff in a world where real men, manly men, didn’t do that because they were real men, manly men. I know this colors my current thoughts. Not because I believe it but because it got so ingrained in my DNA.
What I really struggle with is the how to “come out” part. In reality it shouldn’t be a big deal. And I don’t want to make it sound anywhere similar to what homosexuals and trans folks go through. It’s just not, they have greater struggles. But do you announce it? Cause then it could make it a bigger deal than it should be and raise the question of peculiarity. Or do you just ease into it and when asked, respond honestly. I want the former cause it’s like tearing off the band aid. Quick so the hair pulling is over fast. I go back and forth between wanting to express why versus just wanting to be left alone with what’s simply my choice, neither right nor wrong. Just my choice.
It’d be interesting to hear your mom’s side of your story. Moms are amazing and have a way of knowing things even we didn’t know they knew. She has been greatly supportive of your choice in wardrobe and even borrowed a skirt as I remember. NPR has the Friday conversations where two people interview each other and tape them. They’re fascinating. Yours would be amazing.
Keep being the excellent pioneer you are
I figure being open and honest about it is the best way to convince others that it’s ok to be different regardless of the path we took to get to where we are. A lot of skirt-wearing men I’ve talked to have had a similar experience to mine which is why I thought it would be interesting to write about.
“Coming out” can be, like you said, pretty difficult. It isn’t as difficult as what homosexuals probably experience, but as we know, it can still be stressful and even traumatic for all parties involved. My strategy depends on the person. I eased into it with my wife’s family, but pretty much just announced it outright with my own. I try to adapt to make it more palpable for them.
Fascinating! I understand this to be a typical path of discovery, but my own was quite different. I’m old enough to have enjoyed the Back-to-the-land movement that grew from the hippie 60’s. The movement was a re-emphasis on clean, natural, and self-sustaining rural living (key book: “Five Acres and Independence”). Also, I have had a lifelong interest in simplification generally (been a key element in career success). So sartorially, those two influences meant I was pretty unconsidered, basic, and utilitarian for most of my years so far: jeans or chinos and a shirt as needed; sandals if shoes were required or useful. I’ve climbed mountains with nothing more.
But, as you will have surmised, I am not young anymore: still fit (-ish) and strong (-ish), but time takes its toll. Several months after doing a brutally hot, 3-day, emergency roof repair that left me severely dehydrated, I found myself in a hospital for the first time since birth, with a massive kidney stone that could not pass. I’ll omit the gory details, but note only that the usual hip-riding top of my pants or shorts was unbearable post-surgery. At first a robe was fine, but as I felt functional and needed to get out again, that wouldn’t do. I slipped on a tunic I had work at Renaissance Faire. Aha! Though it’s pocketless, rough twill was not practical daily garb for most activities, it was adequate in the yard and for some errands. Looking for something more flexible, capturing the comfort of that tunic’s fit, where the waist is at the waist, not the hip-top, lead me to find jean skirts! Riding at the true waist (away from the still-tender zone), made with cotton and just enough stretch, fitted with four real pockets (for keys, phone, wallet, and cap). As a bonus, they look GOOD (first approval came from wife)! From there, more colors and cuts, more fabrics, too. Now my daily wear, and life goes on, comfortably and more stylishly than ever before.
Your path was certainly very different! It’s really amazing how many benefits skirts and dresses have over pants and that most men choose to miss out on them!
I can relate so much to this story. When I was a young child my mother stored a few of my sister’s dresses on one side of my closet, and later, a few of her dresses and skirts. One day a childhood playmate and I experimented with trying on the dresses, and from that point on I was hooked. I would later transition to my mother‘s dresses and skirts that were in my closet— always in secret. The feel and swish of of the material on my legs felt amazing.
I have wondered if I hadn’t had that temptation to develop curiosity about wearing skirted attire if I would have incorporated this desire to wear some “femimine” fashion into my persona? If I had the ability to change what transpired to the point of me not developing the affinity for skirts and dresses I’m not sure I would. It’s been a curse and blessing. But overall, I think I’m better off for embracing some degree of femininity. It’s helped me to be a more complete, accepting person. God made us individuals—we should accept and be thankful for that fact.
Hey Brent! You use the word “temptation”. If you found a lacrosse stick in your garage and that led you to play lacrosse would you use the word temptation?
You were a kid. Likely didn’t have a strong sense of gender norms. So you tried it on and liked wearing a dress.
But because we have these silly gender norms, did you place more emphasis on playing with a dress versus say playing with a lacrosse stick?
Greg,
Yes, I was tempted by the dresses- a feeling that was exciting but also embarrassing/shameful because “only sissies” would be interested in putting on a dress. Boys are trained early in life what’s appropriate for them and what is not. Hopefully, that antiquated mindset is dissolving with time.
You’re right- gender “norms” are ridiculous, especially considering the double standards that exist between males and females.
At that point in my life I probably would have been more interested in a lacrosse “kilt” than a stick. Ha!
Ha! Lacrosse kilts!
When I was a senior in high school, they started the girls lacrosse team. They wore skirts. For one game, I don’t remember how it happened, but I got goaded into wearing one of their skirts to the game. I wore it briefly over shorts and then gave it back. I forgot all about this experience until you mention lacrosse kilts.
It is too bad we place restrictions on a child’s play.
I’m glad you can relate! Your story certainly sounds similar to mine. I have also wondered how things would be if the dress hadn’t been hanging in my closet, but I assume I would have come across it at some point in my life.
I hadn’t even think about wearing a skirt or dress until about 2005. I was home alone, wife had to work that weekend. I was board, the weather wasn’t good to go for a run or a bike ride. Well being a good husband I was cleaning the house and doing laundry. Well folding and putting clothes away there was a nice fleece skirt. so I closed the shades and put it on and wore it most of the day. It felt magnificent and I wore it every time she had to work and I didn’t. I was sad when we got divorced, I lost my access to wearing a skirt. Fast forward to 2019 and while backpacking bumped into a guy hiking the CDT wearing a kilt. we talked about it for a while. Six months later I started doing some research on hiking kilts/skirts. I found a couple companies that made hiking skirts, both US based and woman owned. So I ordered a skirt and would only wear it at home. I started getting a little braver and started wearing it to walk to the mail box and walks after dark. Well one day walking to my truck, mid day, one of my neighbors saw me and said “look at you rocking the kilt”. Well that boosted my confidence 1,000%. So I started wearing my hiking skirt to the store, and again no negative comments. The next step was wearing them to work, and again the world didn’t come to an end. That was the defining point in my skirt wearing. I wear my skirts every day now, and I have a closet full of skirts, 30 or so, and a couple of dresses.
It’s amazing how a simple compliment can really change things for us for the better. I also wouldn’t be as confident as I am wearing skirts if it hadn’t been for the compliments I have gotten in them.
Nowadays I don’t really like black clothes – I get it that they’ll survive longer, and not indicate any dust or dirt especially during autumn, but this really implies on your mood and wearing black top+bottom is as common and generic, as these denim trousers – but when it comes to black dresses, well that’s a different story (although still I think going for slightly lighter colours is better). I totally understand the fascination of trying such dress and you know what? There’s a bunch of things we should try in life (that are no “clearly nonsense”) and I’d recommend every male to try it just to know how it feels to wear a dress. Even if you’ll go to the mirror and say that it’s not your thing or you feel like looking just ugly and awful, you could at least know this other perspective. So far my experience with a dresses isn’t really a long story, I use few as nightgowns since I found them in my mom’s wardrobe and these had shreds already, but I’m thinking about giving it a go with some sweater – it could be still considered as high waist skirt
That’s fair enough. I’ve always liked black and other dark colors, so I still tend to wear a lot of them, but I can definitely understand why someone wouldn’t want to. There really are a lot of things that people should try in life and wearing dresses is definitely one of them! Wearing a dress as a nightgown isn’t a bad idea at all. I wear actual knee-length nightgowns which are more or less dresses if you think about it. I bought them from the men’s department though because the cuts fit my upper body better.