Monday, April 17, 2023

Crossdressing Sans Skirts

When I started crossdressing in the early 1960’s, women wore skirts and dresses much more often than they wore pants and trousers. As a result, I always wore skirts and dresses when I crossdressed. Pants and trousers were never a wardrobe option. After all, they didn’t call it crossdressing for nothing! If I wanted to wear pants and trousers, I could remain in boy mode and not get pretty.

Times change. As the 20th Century wound down, women wore pants and trousers as often as they wore skirts and dresses. And approaching the quarter century mark of the 21st Century, many women have abandoned skirts and dresses altogether and wear pants and trousers exclusively.

As fashion mores changed, I stuck to my guns and refused to wear pants and trousers and only wore skirts and dresses in girl mode. But I finally relented circa 2010 and began adding bifurcated bottoms to my wardrobe including shorts, jeans, slacks, suits, etc.  

I still like to wear skirted womenswear, but do not shun pants and trousers as I did in younger days. And I’d love to rock an outfit at work like the one featured in today’s Femulate Her slot below. Wouldn’t you?


Source: Ann Taylor
Wearing Ann Taylor

Donald Dillaway
Donald Dillaway femulating in the 1934 film The Circus Clown.


  1. You know, I've been trying to figure out the answer to this too. I wear a dress or skirt pretty much every day to work, but I'd really like to explore adding pantsuits into the mix!

  2. I have femulated precisely twice with bifurcated bottoms and although I must admit that a pair of straight leg woollen trousers looks breath-taking on a tall gal, I could not surmount the unease of everyone staring at my crotch, presumably wondering where was Waldo. So, it was fun but never again.

  3. Sorry Stana but you are not allowed to take days off! :)

  4. I am a child of the 1960's. In my neighborhood women only wore dresses and skirts. There was one woman who wore pants and she was also divorced. She was avoided like the plague. Girls had to wear dresses to school. If it was freezing out and the snow was deep the girls could wear snow pants under their skirts but had to take the pants off after arriving at school. My family watched Ozzie and Harriet & Leave It to Beaver. I suppose those women influenced me. For me it is a dress, hosiery and heels, and all the proper undergarments. In the 1970's my wife worked as a receptionist for a book company and was required to wear dresses/skirts and hosiery/heels. She cursed the cold weather waiting for the elevated train. Frankly, I am still somewhat confused why a cross dressing man would don women's trousers or jeans when there are so many other options.

  5. There's been a few articles about shorts being in this year. Well, tailored shorts at least. They've got to try and sell you something new 😉 It doesn't seem that long ago that city shorts wetter l were a thing.

  6. Hi, I found today this Peanuts strip in GoComics, thought you might like

  7. My mother works second shift in a factory I would leave for work every day around 3 o’clock in the afternoon, Although she wore a uniform on the floor of the factory, it was a dress what is the company logo on it. But she was sure to arrive for work in heels I was every skirt dress or slip high heels and make up

    I would watch her get ready in the afternoons many times putting on her make up she will give me instructions for the evening

    I think this may have been a big influence on me and my style of dressing I like you stoner would much rather wear A nice dress or a skirt along with heels and pantyhose.

    I would envy the girls in high school when one day a week, when they had house class and didn’t have to change many of them would wear dresses and stockings it was my favorite day of the week

    I graduated high school went off to the Air Force and really wasn’t around women much when I came back and got a job in the business world I was floored, it was a 1980s big hair make up dresses pantyhose in high heels I remember getting my first paycheck and going to the mall and buying a dress

    And so it goes

    Paula G

  8. Stana, you have expressed my sentiments precisely. I would always think, why would I wear something other than a dress or a skirt... in guy mode that is all there is, just the wonderful selection of bifurcated garments of some sort. As time went on and living in this part of Florida skirts and dresses are certainly on least worn items you see when you are out. So while trying to blend, I have drifted a little more towards pants. When I am out most of the time I prefer the skirt and top, but I have found that nice pants along with some heals can be fun as well.

  9. I avoided anything resembling trousers for years. As has been stated - if I was going to wear pants, why bother cross dressing. But then there's the "blending in" question. That's why I started wearing leggings with a tunic top. Very close to a dress and pantyhose/tights, but not enough to stand out. I still prefer skirts, but it depends on where I'm going. Saturday morning grocery shopping -- leggings. Sunday afternoon at the mall -- skirt, like I just came from church.

  10. I cannot for the life of me understand why women dislike wearing dresses. They look and feel wonderful and radiate femininity. I really believe women have an advantage over men in our ability to wear dresses. I have been wearing them whenever I had the opportunity all my life and regularly socialise and do everyday tasks as a woman always in a dress. I have never felt out of place or overdressed even when I am the only woman in a dress. Of course the trick is to wear an appropriate dress for the occasion. I do not own any ladies trousers and cannot imagine ever wearing them. To each her own but I adore everything that comes with wearing a dress.

  11. Stana, you're amazing! As usual, I looked around the 'net for more information on Donald Dillaway. All I could find was a handsome leading man and searching "The Circus Clown" yielded nothing. How do you do it?? I guess I'll have to rent the movie to see more of "her"..

  12. The brunette in the Femulate Her slot really rocks the look, although I don't think I would try it. In a flowing skirt, it is a lot easier to give a feminine impression than it is in leggings and a jacket.
    Penny from Edinburgh.

  13. Much the same experience. I was passable up to around 1980 and then age and a career move gave me two choices: give it up or put on makeup with a putty knife. But I LOVED everything about wearing women's clothes and one day realized how much women's casual clothing was being styled in a masculine manner. It wasn't nearly as femme as what I'd enjoyed in the past but I realized I could wear women's clothes 24/7 and only a close examination would reveal what I was doing. I have a few dresses for entertaining at home, but there's almost nothing in my wardrobe today that was made for a man. Just one go-to-funerals suit, dress shirt, and tie. Even my work boots are a woman's size 11.