History of "Dressing Up"

History of "Dressing Up"
As a lot of men did when they were young, I spent a lot of my adolescence playing dress-up with my mother's clothes. Growing up in a religious family, I always had to rationalize my attraction to men. Once I got older, "Dressing Up" went by the wayside. I started dressing again long after I had come to terms with myself.

Not so recently, I separated from my wife and my love for tights re-emerged.  At first, I bought tights for men, mostly ordering compression tights. I learned that they helped after sports, and that was my excuse.  Eventually,  I noticed that my sneakers looked odd when I wore my tights.  So, I ordered heels. Then, my shorts looked odd with my tights and heels. I decided to order some skirts. I tried to coordinate my t-shirts with my skirts, but sometimes they were mismatched, so I started ordering dresses.

You would think this was easy to do. It wasn't, so I had to rationalize it. I first started with the simple question of "Why could women wear menswear, but men couldn't wear womenswear, even if they were designed for men. Sure, some people did, but they were usually rich, famous, trendsetters, or trying to be.  Having studied some Latin in high school and Art History at University, I knew the Greeks and Romans wore what the modern man would now call a skirt or a dress (Yes, I know the Romans wore other clothes under the toga, but you know what I mean.)  Even before I started feeling gender fluid, I had studied fashion during the ages, usually the medieval and Renaissance ages.  That's when I noticed that men in paintings were wearing clothing that would now be considered feminine: tights/leggings, wigs, makeup, heels.

At this point, I want to mention that people, until the Industrial Revolution, either made their own clothes or had someone make them by hand.  This affected the cost of what people wore.

We'll start with skirts and dresses first. I mentioned earlier that the Greeks and Romans were known for men wearing what could be attributed in modern times as being dresses or skirts. They were long or short and flowed, in other words, there was no meeting of the material in the crotch area.  Even the Roman cohort was depicted as wearing plated (not pleated) skirts. The Romans incorporated the Greek culture into the Roman Empire, so what caused "skirts" to disappear from clothing men could wear?

Well, the Romans had a few problems with a few tribal barbarians that in the end overran the Empire.  Guess what they wore?  Trousers.  In Roman sculpture, the Germanic tribes were always depicted as wearing trousers.  Once they overran the Roman Empire, Roman clothing was viewed as decadent and weak.  As an example of the remnants of Roman male clothing, look at any Roman Catholic priest, as they are a remnant of that era.

Next, we'll discuss tights and hose, my original weakness.  Prior to the age of fashion, cloth tubes or animal wrappings around the legs were the best way of keeping the legs warm.  So, the Germanic barbarians that removed skirts from clothing that men could wear, introduced wrapped cloth around the legs.  Over time, as cloth from the East and methods of sewing cloth improved, the wrappings started looking more like modern tights.  The Renaissance has many paintings that depict men in tights.  As the Renaissance progressed into the Enlightenment, stockings became the preferred legwear of choice for men.  With stockings, they used their knee-length trousers as garters or in some cases they
actually wore garters.
Source: https://bit.ly/38fYDpN

Next, we move on to heels. Heels are currently the epitome of female sexuality.  However, did you know that heels were originally reserved for men? Heels were a weapon that warriors originally wore as the invention that allowed horse riding cultures to rise up in their stirrups and shoot their enemy with their bows without dismounting from their horses.  Over time, when wars depended less on archers on horseback, heels were still reserved for the nobility as a sign of their past warrior history.

Wigs are something that has always been worn by both genders since time immemorial.  Why would I say that?  Well, humans have been plagued by many parasites that tend to live in our hair.  Lice were the major ones.  Body lice, hair lice, and pubic lice have been a source of annoyance for as long as man has existed.  One of the ways humans have combated this foe has been through the shaving of hair on the head and body.  However, humans still use hair as a social tool, for both men and women.  Humanity created wigs to cover the removal of their hair.  However, wigs tended to be very expensive, and most cost an average person a couple of year's wages to purchase.  Those who could afford good wigs were usually wealthy.

Let's go back to the Renaissance.  This was the time when the middle class was starting to grow in a lot of countries. They were merchants, adventurers, mercenaries, or craftsmen that were able to take advantage of the new economy.  To show their wealth, they began to emulate the nobility.  The middle class began to wear heels, wigs, and hose as they gained the wealth to afford them.

After the Renaissance, the Industrial Revolution began.  The poor couldn't emulate the rich and mighty, as they were just trying to survive.  The middle class found that supervising their workers in wigs and heels could lead to death or injury if said garments were caught in the machinery.  But, even during the Industrial Revolution, men were still portrayed wearing clothing that we now consider reserved for women, usually at social functions.  And, women continued to adapt clothing from men so much that items men used to wear (and weren't for safety reasons usually) were beginning to be associated more with women.

But, what was the event that defined what was masculine and what was feminine?  It was the Victorian Age and the reach of the British Empire at the time. This one era defined what respectable men and women could wear.  The "Sense and Sensibility" of propriety came to the forefront. Men could not wear what women wore, and women couldn't wear what men wore. It was the "idea" of crossdressing that became an issue, along with other LGBTQ+ hate crimes.  This was the death and the knell of men wearing "fashionable" clothes for over a century.

I hope you enjoyed this brief, rambly history lesson.


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Thank you for the interesting and informative history lesson. Some of it I knew and some was new to me, but well worth the time to read. History aside, I just want to wear whatever makes me feel good in that moment, whether it’s men’s clothing or women’s. I just started cross dressing (I’m so happy I can say that without any shame!) last month, mostly panties which I LOVE and some beautiful nighties. My wife went with me yesterday to goodwill and she found what I couldn’t, two beautiful cocktail/party dresses! Together we found two simple but pretty white blouses and a pleated skirt that is black with big white polka dots! Unfortunately the red dress is too small, but the coral colored dress fits fairly well. If I trim off another twenty pounds it should look very sexy on me! It will be a long time, at least a year, before I can venture out of the house dressed as “Jill” my feminine persona because I have a lot of work to do and many things to purchase. As I’m writing this, I’m wearing a very pretty and super soft and comfortable night gown that my wife picked out at a department store. She is awesome! Love, Jill


I too started cross dressing on occasions wearing things I borrowed from my Mother. Then by the time I was in college I started buying my own things, under dressing as well as cross dressing. Well to make a long story short a while after graduating I met and started dating a gal and on our second date it happened. We did a lot of talking and on our second date she had seen a show on TV about cross dressers that had intrigued her which interested her and she had to tell me all about. That lead her to ask me if I had ever cross dressed or considered it. When I told her ‘yes’ this excited her and she wanted to know all about it. At the end of our date she made me promise I would cross dress for her on our next date and I did. One thing lead to another, she had me going further and further in my dressing and in fact after a year we got married. Since then it has continued and now every thing I own and wear is women’s.


A very interesting article that answered some questions long held in my mind. I love wearing women’s clothing and have long asked that question: Why is it acceptable for women to wear men’s clothing but not for men to wear women’s clothing? Over the last 5 years or so I have gradually tossed out my “men’s” clothing and replaced it with women’s clothing. Now, nearly everything I wear everyday, all day, is made for women. I wear a bra (42C), panties, women’s boot cut jeans, socks and a women’s denim vest – to hide/disguise my breasts. Also, I get my fingernails done regularly done in an acrylic French Tip style and get a pedicure with gel polish of various colors. At night in the warm summer months I where a women’s lace nighty or babydoll nighty. On the weekends I LOVE wearing my wedges or Maryjanes with my boot cut jeans. I love pretty, lacy things. Why should the girls have all they fun, right?


Hi Kyrstin – I’m going to get my nails done today for the first time in months. I’m so excited! I’ve managed to keep them in quite good shape but they could do with some more expert shaping. I’ll probably go for a subtle nude colour although a celebratory red is very tempting. How did you get on with the leather shorts? I love wearing mine!

Ally x


Great overview of men’s attire over the centuries, Histrionics. Totally enjoyed it! You have inspired me to go out a follow the example featured in the beginning of your article. Thank you!


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