Dress Him Up

Why do men never wear dresses or skirts? Why do men always wear pants? And women get to choose? It seems to be a cultural norm in most human societies. Perhaps pants facilitate movement of the legs. I can understand how pants are useful for jobs like construction. Are men anatomically “suited” to wearing pant? Is there some gene that predisposes human men to decorate themselves a certain way, different from women? What about other cultures’ acceptance of certain skirt like outfits, like kilts? (That link has some hilarious photos revealing the limitations, or one could say, overexposure, of kilts. Beware.) Or what about Dhoti’s from India? Or perhaps sarongs from Indonesia? (I found this cute site with the proper way to tie a sarong, and some fun suggestions for this versatile skirt)

Perhaps men haven’t found the right designer to accentuate the leaner lines of a man’s body. Men’s bodies are shaped differently, with narrower hips. I’m sure if the interest were there, a designer would accommodate. I seem to remember some trendy version of kilts showing up on fashion runways for a few years, but it never caught on. Here’s a site where skirts for men are sold. Men in Skirts.

I have worn dresses and skirts. I once found a $50 bill in my dresser drawer, and decided to do something out of the ordinary. I went out and bought a black sweater dress. I am very tall, slim, with no hips, no chest, and pretty broad shoulders. I had a female friend in my orchestra who liked to wear tuxes to work. She was straight, and very fun and cool. She looked great in a tux. I looked pretty good in the dress. We decided to gender bend a little.

So we decked out in the opposite sex outfits, me in my dress (no makeup, just a man in a dress) and her in her tux (with long flowing hair and big boobs) And, on New Year’s Eve we joined the masses of wealthy, upper class revelers at the Kennedy Center. We waltzed (I can’t remember who led) through the grandiose atrium hallway, floating across the royal red carpet, the crowd parting magically before us. We had a blast. (However, my PMS ruined the mood and I slapped her for looking at another woman. Or was it a man? No, actually the dress constricted my movement, and prevented me from doing my finale, a full split at the end of the dance.) In fact, nothing dramatic happened. We just had fun, and lots of champagne.

Another time I wore a skirt with a T-shirt and very large hiking boots to a dance bar in DC. I danced my ass off. It was comfortable and freeing. Though I still didn’t do splits. I’d skip the boots next time around, though. I had blisters for days.

At other times I’ve worn loose skirts. Now that’s comfortable!! Especially with no underwear in the middle of summer. AHHHH! (No problem with the splits, either.) I prefer those ubiquitous Indian wrap around skirts. They come in a fun variety of rich patterns and colors. And one size fits all. Never bunch up in the crotch.

I’ve been to a couple of Faerie gatherings, where men wear anything they want, or nothing at all. Some faeries wore 2 or 3 different dresses a day. Like a mood ring, only with dresses to express the mood. At first it was almost offensive that men, sometimes fat and hairy men, would prance around in wedding dresses. I was intimidated by their audacious freedom. I was paralyzed by my own judgments of them, and the implied judgments of myself. “I would never do something so, so…” So what? Free? Random? Different? But after meeting several of them, who usually turned out to be articulate and sensible men, I realized I was the one with the problem. I met doctors and lawyers who just wanted to let their hair down, so to speak. Soon I was enjoying every rule shredding moment, sifting the bogus chaff from the real seed, the playful core of my self. I didn’t wear any wedding dresses, but then again, I didn’t come with my own wardrobe, either.

Except those times, I’ve almost never ventured away from pants. I feel it would go against the accepted behavior for men. My rebellious days are over. It would attract too much attention. It would be considered weird, freaky, comical. What a shame.

I imagine a society where difference is really accepted. Where I can swish around in a park on a summer day wearing a loose skirt and a T-shirt and perhaps see someone else doing the same.

Dresses are comfortable, and freeing, both for the body and the spirit. I don’t think women should be the only ones with that freedom (or choice of fabulous wardrobe elements).

41 thoughts on “Dress Him Up

  1. I hate wearing dresses! Never did find them freeing – they came with so many rules about “sitting like a lady” and being careful what you “showed”. Maybe it s because the last time I wore them was during the miniskirt era! But I know some other guys who like to wear skirts so I’m glad someone likes to wear the darn things!

  2. I agree. Clothing should be totally the choice of the wearer…not what society dictates.
    I’m not a man, but how about a sarong? I’ve recently ‘discovered’ them (ha! I’m only several hundred years behind) and they’re amazingly comfortable. I could definitely see a man in a short sarong, t-shirt and sandals….though a pair of boots might be….interesting, as well. hehe

  3. I think it would be fun to wear a Kilt out one night and see how it feels! The freedom could be exciting!

  4. I found this post fascinating. I’ve often wondered about many of the questions you posed. I enjoyed reading your opinions and your experiences.

    PLus, I see a bonus in the comments thread. 🙂 Not only did I just see you on Stormwind’s site, a gem I recently discovered a few wks, ago, I see another longer time net friend above: Guusje! 🙂

    She and I met via Julie’s bookworm site. (I am listed as Green-Eyed Lady or Good Vibrations on their links.) Sorry, klutzy me needs to learn how to insert links to others’ site in text.

    Take care!

  5. Oh, I love to wear dresses and skirts. Pants are so constricting! As for commando, oh yes! (but not when there is a strong wind or when I”m ballroom dancing w/ my partner.) I, too, love to dance!!!!!
    Our society is most emphatically more accepting of women wearing different attire than men. I wish that would change (among a few billion other outrageous rigidities) pronto!

  6. I agree that men should be able to wear whatever they like. I’ve worn skirts before but not out in public. I love skirts. Like you said it’s a shame. I also like women’s shoes…they are much more stylish then men’s shoes. Men don’t have much to choose from in shoes or clothing. I wear earrings and dig those too. Although they are very “manly styled” earings (whatever manly means). I’d love to wear those stringy earrings that women wear now that are so in fashion.

    It’s really too bad that people see being accepting as being “abnormal” Hmmm, attachments are so dangerous. Attaching to a certain “code” in society can bring so much suffering, judgement and segregation.

    Great post!!

  7. I am a man and I would love to be able to wear a skirt in public. I am going to work wearing a wedding dress on halloween this year, which is a huge first for me as I don’t usual dress up for halloween.
    It’s been interesting, when I bought the dress, and when I took it to the dry cleaners to have the straps altered, I had to try it on, both times, and no-one did anything other than raise a friendly smile. I think that it will not be difficult at work either, because the people I work with are an intelligent, friendly bunch.
    But I wonder, what would be the reaction if I just wore a skirt and blouse on any other day, especially as I like to wear quite flowing, flouncy skirts and dresses.

  8. jules- Kudos to you for your courage, and for understanding the power of conformist culture. Men should be able to wear floucy skirts. I wear them at home. At least no one can bug me about it then.

  9. Hi, I too like to wear dresses and flowing skirts and I like the feel of lycra tights (just love em in winter), but one thing I do find hard is to get any sort of decent dress these days as there is a trend away from dresses. I love wearing dresses/skirts in public (my wife hates me doing it). I have been asked to leave a suburban shopping centre because I was wearing a mid length casual flowing dress, apparently I was not suitably attired.

  10. Alex- I am appalled that you were asked to leave a public place for wearing a skirt. How sick “normal” culture can be!

    Thanks for your comment.


  11. i think that all men should make just 1 day THE day and us all that are men and not afraid of our masculinity or our sexuality put aside the fear of being laughed at or whatever we are afraid of and just dress the darn way we want and not stop untill it is accepted i for one will do what ever it takes tv or whatever if i could get a few to sponser me and to back me up! give me some feedback here

  12. tommy- thanks for the note. It’s just one of those things, where society as a whole is a bit retarded and just doesn’t or chooses not to understand how stupid it is to think men MUST wear pants. As you suggested, it would be cool if there were a national “gender bending” day. Perhaps I’ll post about it sometime.

    take care,

  13. I have been wearing everything from dresses to micro mini skirts for the past twenty years or so . Iv found that people are becoming more accepting of men in feminin attire . I make no attempt to hide the fact that im a guy althoe i do have 38 B breasts. mostly i just dress for my own comfort. I rarely dress in male clothing weather at home or work or the mall. I recently moved to a rural community . Ive recaived mixed reactions from a lot of people but none hostile. Mostly what ive encountered is curiousity. I have had lots of women aproach me over the years and ask how to convince their husbands or boyfriends to try it. Im a married man with kids in a wide array of ages.

  14. raych- I am simply amazed and impressed how many straight men are helping “gender bend” all the ridiculous and limiting rules of our culture! Thank you so much for taking the time to comment. I need to post about this again to encourage even more men like you to stand out!!

  15. I have been wearing the shirt dress style. A little old fashion but very comfortable. Been doing it for years. Problem is I am stuck in the house or in my yard only. Very tough to take the dresses off and put pants on to go shopping. Would love to be able and free enough to shop for new dresses and wear them in public with out getting locked up.
    Will go to the grave with my secret.

  16. I would love to be able to wear a dress all the time but I am afraid of being ridiculed at work. I wear one whenever I can and the feeling of total satisfaction that I get is marvellous.

  17. There seems to be no end of people who take some relief, comfort or pleasure from cross dressing. I posted last year at this time, and dressed up again at work for halloween this year as a french maid, only this time I went all out, wig, makeup, nail polish, stockings & garter belt, lacy knickers, petticoats, 5″ heels & all.
    I have begun to find that much of what attracts me to cross dressing is that I enjoy the way my nails look with polish, or my legs with high heels, enjoy wearing attractive or sexy clothing, and the tactile pleasure of soft, feminine materials and I don’t subscribe to an arbitrary convetion which denies me this pleasure.
    But although my colleagues at the office and the neighborhood in general complemented me and found great entertainment in my costume (which was pretty convincing despite the rarity of women standing 6 feet 8 inches in heels) I found that even my loving, understanding and long suffering wife grew concerned when I kept the nail polish on for a few days afterwards – even though most others did little more than raise an eyebrow.
    Latent conservatism and fear of deviation from societal norms is the big issue. I tell my wife that we are society, we must set the norm, and freedom of expression is a constitutional right, but these issues are so deep seated – even my teenage daughter appears to have been indoctrinated by the system, although I hope it’s not to late for her.
    We have to be subtle and discreet, smart and above all, both brave and persistent. Long live the revolution!!!

  18. I wonder if society will ever change, with religious conservatism strangling any notion of gender bending. It just seems stupid and absurd to me that men can’t dress pretty if they want to. The sickness is in those who won’t allow it, not in those of wish to cross-dress.

    Good luck with your attempts. Just don’t get hurt.

  19. I have cross dressed for years and I’m not about to let some small minded idiots stop me from doing so now.

  20. I love skirts and as far a gender bending – up until around 1760: a skirt was ‘mens attire’. Women wore the longer skirts and men wore the shorter skirts. I have a full Kilt outfit that I wear occasionally, which my wife says makes me look totaly masculine and she loves to be on my arm as we go to a very nice restraunt. I would love to wear a jeans skirt with a sport shirt out to the grocery or hardware store, just dont have the nerve. I just dont want to deal with any ridicule. This is something that will have to come about by everyday men wearing, rathur than coming down from the fashon designers.

  21. Hi,
    I live in my own and at home I wear nighties,skirts dresses its feels so good.
    Outside all I dare wear is knickers.
    I am glad I am not alone in this

  22. I wear a dress whenever I can. It’s far more comfortable than wearing trousers all the time and there are plenty of bright colours to chose from instead of miserable blacks and greys. Why shouldn’t men have a choice?

  23. David, it has been fascinating to follow this thread for nearly two years since I posted just before Halloween 2006. I loved wearing my wedding dress back then, and I dressed as a french maid the next year, and I now have an extensive wardrobe of clothes, (I am particularly partial to DKNY!) and I go out frequently in my female form. I rarely spend money on male clothes these days, because most of my social life is spent as a girl. I spend a lot of effort keeping myself in trim and on suppressing obviously male aspects of myself such as facial hair. I dress appropriately for my age and frequently go to mainstream restaurants with straight friends and trans friends. I have taken makeup lessons and am quite passable as a girl. Soon, I will be going on holiday to Europe for the wedding of two of my oldest and best friends, who told me quite sincerely when I revealed my TS state to them, that they would be flattered if I felt comfortable enough to come to their wedding as my female (and as far as I am concerned, true) self.

    I first posted here when I was beginning to feel bold enough to take action and acknowledge my feelings. I now realise that I am no pervert or weirdo, but a fully functional and highly constructive member of society. I am successful, professional, well liked and look my peers in the eye, and they do the same, and compliment me upon my taste! Now I know I am privileged, but I also know that many in my position shy away from precedent, where I do not. I have no agenda, and hold nothing but contempt for those who would judge me for my choice of gender expression. I suggest we look to Europe. The UK branch of my company publishes a policy which explicitly protects the trans-gendered, and this is not in response to enlightenment, but to federal legislation.

    Whether you wear a skirt because it is cool during the summer, because you feel like it is the appropriate garb for you within our society or because it turns you on, all I can say is, stand up straight and look yout neighbor in the eye while you do it, because this behaviour does not define you and you cannot be judged by it. Those that judge you are beneath contempt. By following this and similar credos I have started to enjoy and even love my life, and about time too!

    Best wishes and greatest of respect, Jules

  24. Thank goodness that there are many more sane thinking people like myself who feel that it is not so wrong to expres yourself properly. As you say, the only ones with the problem are the stupid bigots who are too afraid to do something out of the norm. Hard luck on them is what I say!!!

  25. Peter- You present an eloquent case for freedom of self-expression through image clothes. Inner strength is something many people do not have. They rely on “fitting in” to give them confidence, but it’s false. Those who do not accept you are weak themselves. I’m glad to see how you’ve grown in spirit through the practice of being yourself and matching your wardrobe to that.

    Garnet David

  26. WOW, I just happened on this site. I love to wear dresses, but I do not dare do so in public. My room mate sees me often in various female attire, but I do keep it in my home. Dresses, skirts, gowns, and all the various undergarments. I love them and hope for the day that I can comfortably even answer the door in whatever I may happen to have on. Thanks for the positive comments here. I will check back often.

  27. I have found when wearing women’s clothes it is best to go all the way. There is nothing worste than a man that just puts a dress on with no effort at all. I mean you need to shave those legs use makeup wear pantyhose and panties everything. Also you need to try to get your head wright get into trying to be the best female you can. Walk with a swhish and try to talk in a higher tone. When you are a teenager up to about age 23 you can get away with doing what women are free to do that is pust the envelope toward what I call being a sissy-boy and freely move around in public. The more you wear femine outfits the more relaxed and comfortable you become and thats the goal you need to work toward. For example I used to be able to wear pink or yellow short-shorts with white ankle socks or even painted toes nails with open toes shoes. Then light make up some jewerly and a tank top. So you can really be your femine self. Otherwise I say go for the whole picture.

  28. Oh my goodness. I am so sorry but I can not stand seeing the whole drag bit being done. It is just beyond gross. But you are kind of right, you should be able to choose what you want to wear. Nice post by the way.

  29. I am always afraid of being “caught”, yet I do things that get me caught often. I have this black sleep shirt. It is made of nylon. The other evening I put on a bra (a padded one) and then slipped on the black sleep shirt. It comes almost to my knees. Then I got my DL, keys, and went for a drive. Now the seat belt falls directly between the bra cups and one can easily see the bra from the perspective. Every time that I was stopped at a red light, I was keenly aware of anyone around me. And my goodness did I feel embrassed. Embrassed, yet excited all at the same time. I did not have on a wig, nor make up. I wasn’t wearing any sort of jewelry. Anyone that looked closely would have known without doubt that this was a man driving around wearing a bra under his shirt. I don’t think that they would have realized that I was wearing a sleep shirt. From even a close distance, you can not tell it is a sleep shirt unless you are seen standing up.

    Oh well, just thought I would share my zaniness. Maybe some day I too can put on a nice dress and just go………anywhere.

    Next time……………

  30. I wear dresses all the time whether I’m in or out and the satisfaction I get from it is so great. If the idiots want to look that’s up to them. I pass well as a girl so I don’t care what they think. I’m not going back to wearing boring male clothes while women have all these great fashions.

  31. I applaud you Peter. I love being as feminine as I can and I do so with my attire. But sad to say, I keep it at home. I do wear panties all the time, and in winter, I often wear stockings. But away from my house that is it. I have not yet had the opportunity to answer the door while dressed fem, but I know that some day I will have that opportuinity. What I do at that moment remains to be seen. I know what I want to do, but I may not have the courage at that time. Anyway, I am proud of you, and I encourage you to continue your life as you know it. Live for your own happiness. Good luck to you.

  32. Girls can dress as blokes and noone even notices. If a guy wants to dress as a girl, then why not? Years ago I dressed up a boyfriend as a girl for a fancy dress party. White frilly blouse (New Romantic was the look), tights and a skirt. Couldn’t find any matching shoes back in those days though. Still, I think he had fun.

  33. I continue to get braver and braver. I very often now go out at night in a skirt and blouse. I have even stopped a couple of times and bought fuel. Of course, I pay at the pump, and i pick rather slow looking stations. Still, I stop, get out of my vehicle, pay and pum the gas. I find it quite freeing, yet very exciting. My next big step is to actually go into a place of business while dressed this way………….but I think that is sometime away yet. How I wish that I had some help here, a sweet woman that would both encourage me, and teach me. Until next time…………

  34. I wore my sisters figure skating dress and tights to our neighborhood holloween party one year (I was 12 years old) and the adrenaline rush lasted all day and evening long. The sensations caused by the wind rushing across my lycra encased body and the little skirt constantly fluttering against my thighs,hips and butt etc was so intense it was actually keeping me dizzy most of the party. I couldn’t get over how great I felt wearing the outfit. I think I danced with every girl in the neighborhood and was pawed by most of the older ones. My sisters told me that almost every one of their girlfriends ended up with a crush on me as they thought I had more guts then any guy they ever met before and thought I looked “incredibly hot” in the skating outfit. Not only did I meet and go out with dozens of girls the next 5 or so years but got to indulge in dressing in figure skating dresses and other skirted outfits when I was at their or our home when no one else was home. I love my sisters for talking me into wearing the outfit and their continued help and encouragement over the years. I eventually married one of those gals and have been rollerblading (still skirted up) with her on the paved trails along the lakefront in Chicago for the past 23 years.

  35. Hi David; a third year has almost passed since my first post on your article, and here I find myself in a situation far from where I imagined I would be. I now spend over 90% of my time in a female role. I am six months in to female hormone therapy and am following various other courses of treatment all with the same goal in mind – I am a committed pre-operative trans-sexual.

    It has been fascinating to follow this post and it has been just one of the many sources of encouragement for me as I have found my path to personal freedom. I have found society at large very supportive, at work (the IT department of a global bank), at home and out and about in middle class suburbia on the east coast, although I admit I remain selective about where I hang out!! These few years have been the most interesting and also the most rewarding and happiest of my life so far.

  36. @jules: Wonderful!! Even though I hardly write for this blog anymore, it makes me happy to know that this one post, with the flood of popular comments, has been a positive influence on someone’s life three years later. Best wishes to you for a long and happy life!!

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