The 5 Things I Learned While Wearing A Dress All Day As A Man

I love to challenge my students in regards to beliefs, societal norms, and cultural expectations.  As a strong proponent of new experiences and change, I frequently find myself encouraging others to try something different in order to gain new perspectives.  I believe this to be of particular importance the older we get—as opening ourselves up to new information and experiences truly helps to keep our minds fresh and challenged.

So, this past week when I challenged a particularly effeminate male student, who basically despises everything masculine, to open himself up to new “macho” experiences in which he may feel uncomfortable, going to an NFL game for example, he cringed.  It occurred to me that perhaps that could be too much, too soon. So I reconsidered.

“Ok, Jack,” I stated, “if you wear an NFL football jersey to class on Thursday, I will wear a dress…all day.”

As a man who has no interest in wearing women’s clothing, I somewhat instantly regretted my offer as he quickly took me up on it. However, I also have no interest in being a hypocrite. If I challenge my students to take on new experiences that go against their natural inclinations, why shouldn’t I?

It turned out to be one of the better ideas I have had in my life

So, the next day, I went with my daughter Tessa dress shopping (at The Good Will…. I knew I would likely never wear it again) who helped me pick out a nice red and black paisley with matching sleeves and a delicious plunging neckline.

And what did I learn from my day dressed as a woman?  5 things. 5 things I already knew at some superficial level, though experiencing it firsthand solidified and greatly deepened my understanding. I realize these lessons are very specifically from the United States perspective of cultural norms.

  • Wearing a dress all day gave me an unusually high level of awareness concerning my, ah, “junk.” A dress provides extremely easy access to the genital area while having to work fairly hard all day ensuring you are not the victim of public upskirt porn or the Marilyn Monroe style blown up dress.  Could it be that we made dresses for women the, essentially, cultural norm in a society that hyper-sexualizes them? I do not claim to be a student of fashion history, yet dresses certainly make women more easily sexually available from a practical, “let’s make this as accessible as possible” perspective. In the little bit of research I performed for this blog, it does appear that the voracious male sexual appetite has always played a central role in determining clothing norms.  Call me crazy, yet when you have to work all day ensuring your genitals do not fall out, a much greater cognizance of their presence is the natural result. As a man with pants we just tuck that bad boy away, zip up, and move on.
  • Wearing a dress all day made me feel somewhat scared and vulnerable.  As I walked through campus and endured the laughs, the dirty looks and even taunts (one young man said, “you wearing that dress makes me want to kiss you,” in jest, to be sure, though it still crossed his mind) I was not sure if I was even safe. Now I am quite certain if I did wear a dress everyday my level of sensitivity would decrease, yet this experience offered me a very small, yet profound insight into the vulnerability some disenfranchised others—such as the handicapped, effeminate males, “bull dike” lesbians or certain out-of-place ethnicities, may feel on a daily basis. Wow. I just wore a dress one day at a college campus as a stunt…while certain people have to live this as a way of life. This experience was surprisingly insightful and has given me a new perspective of cultural outliers.
  • Wearing a dress all day caused me to reach a higher level of critical understanding concerning cultural norms and practices. Why shouldn’t men wear dresses? It is just fabric that covers the body—which is really the entire purpose of clothing. Why have we attached such strong gender specific identification to clothing? It is just…CLOTHING. Who gives a flying f? Who was the council that got together and declared what is for men and what is for women… and what was the logic behind it? It makes absolutely no sense from a strictly “do things rationally for a valid reason” perspective. I realize that some men wear dresses as official garb, such as priests and supreme court justices, yet that is designed to place dress over existing clothing as to not let the outfit you are wearing underneath play any form of distraction in official proceedings. What other bullshit cultural norms do we we buy into everyday? This experience really has me thinking at a higher level of consciousness concerning what we do and why we do it.
  • Wearing a dress all day made me realize society has a double standard: Women can dress like men and it is socially acceptable though men cannot dress like women. Ok, my daughter, Tessa (the one who likes to go dress shopping for her dad)  disagrees with me on this one and I understand her point and do not necessarily disagree with it.  Her understanding is that this double-standard really is not a double-standard at all.  Men are the powerful in society and to emulate one through dress is acceptable; to emulate the less powerful is unacceptable—and perhaps this is true, yet, it still creates the same result —there is a stigma against males dressing as females, whatever the reason. Ruth Greyraven, a card toting member of the “female who dresses as male” club and biology professor at Crafton Hills College, had this to say about gender and clothing on Facebook:

Since 1968, I’ve been participating in a social experiment where I wear “men’s” clothes. I got sent home from school and threatened with expulsion the first few times, even when the outfit was a girlie-colored and femme-cut pantsuit. Times changed for women, but not as much for menwomen don’t get arrested for cross-dressing in this country. And a butch woman is far less likely to be beat to shit by queer bashers than a cross-dressing guy.

Agreed Ruth. In my courses, most female students do not wear dresses, rather, mostly, jeans and a t-shirt…traditional guy clothing. However, to my point above, why does this double-standard even exist? Clothing should not be an issue in the first place. Wearing a dress all day reaffirmed my commitment to continually challenge myself and others to test all cultural norms. Why? Not to be different, arrogant, unwilling or defiant—rather for the purpose of assisting the evolution of culture to be more loving and accepting of others, and, secondly, for the purpose of personal growth. As mentioned above, what else are we doing in 2016 that is traditional though not logical; unacceptable but with no basis; insensitive and for no good reason? Clothing is likely just one cultural contradiction of many.

So there you have it, my day dressed as a woman, in a dress. I had absolutely no idea the profound impact this would have on my psyche.

I dare you. Step out and explore new realms.  You will have no idea of the effects it may have on you, the individual, and culture, the collective. Jack did it…so can the rest of us.





  1. I think Jack’s sandals would have looked better with your outfit.
    Good for you for opening more young minds and probably starting many conversations…. all positive steps!!

  2. As you know, it’s human nature to observe and then do experience, once we done experience we like to do action, depending upon the outcome of experience, once we do action that’s become a part of our character trait. Right
    Believing on this human ethics and try to stay within norm of a human species, I would like to try experience but my action will be after knowing the after effects if my experience.
    Anyhow I like your hair style which suit on your experience but I am woundering to predict your action

  3. Well, Jimmy …. What can I say. Welcome to the wild side? However, reasoning has everything to do with expression. I’m fairly certain that you know what I mean. Your reason to wear a dress was to acquire a certain level of awareness and understanding. For that you should be applauded. As you are keenly aware I wear dresses to express an inner characteristic which is very basic to my nature. However, all in all, wearing a dress for one day was an expression of your inquisitive mind and nature and I applaud you for the courage. Next time, though I think you should go all out; with heels, make-up, shave your legs and armpits. On second thought … maybe not.

    • Georgia….thank you for the response. I do believe my one day experiment is exactly that…one and done. The only thing expressed for me was more my personal curiousity. I think it is sad that doing this is “courage”….and I guess it is at some level, yet, for me, it is really much more an expression of not giving a shit about people’s judgment and that attitude plays well into social experimentation.

  4. Tessa has excellent taste in dresses, but that is NOT a deliciously plunging neckline, thank goodness.

    • Don…with my wide shoulders I was very limited in options. And I just wanted to use the phrase, “delicious plunging neckline.”

  5. Professor Urbanovich you were very brave on wearing a dress to school, I applaud you for that! It takes a real man to do the challenge you did. I think that back then judment of gays, lesbians, and transgender were more of a surprise and offensive to most people. It can still catch us off guard if we see a man with a dress walk next to us. Just like the students at school that saw you weird and made comments because you were wearing a dress. I believe it is more acceptable now a days treating and accepting transgenders, gays and lesbians. Many people think very unethical of what you just did, but like you mentioned above it is just CLOTHING! Why aren’t people so judmental knowing that scottish men wear skirts? Or when girls dress as guys(tomboys) I can’t really argue with this discussion because I agree with you to the full extent. I am glad you got something out of this challenge, and that dress does not make you less of a man. Today’s society needs to be more open minded and accept peoples preferences. If you were a student in my class that would wear a dress everyday to school, I know I wouldn’t treat you different. Why, because you are a human being just like everyone else and that dress would not make you any different than all the other guys in class in my opinion. I think many transgender, gays, and lesbians suffer from low self-esteem due to not being accepted by society. Props to jimmy as well on going out of his comfort zone and wearing what he wore! Your experience also taught me something, to not judge a book by it’s cover and accept and treat someone the way you would want to be accepted and treated.

    • Wow…thank you Karina! I am so glad I did this as I learned so much. I would really love for someone to offer me a counter argument (based in reason) why something like this is unethical. What would be the grounds for such a statement? All I can think is it violated cultural norms and is taboo…but that makes it neither wrong nor unethical -it makes it different and people are scared of different. I really appreciate your open attitude Karina!

  6. Hello Jimmy, this is a very interesting take on how to challenge yourself to do things out of your norm. I just don’t understand how dressing like a women will help you beak out of your shell. Those gender roles of what clothing to wear are there for a reason. But I do like how you challenged that. Sometimes seeing another take action and challenge something, will get you to take action yourself. How ever I do agree when you say anyone can wear what they want. There shouldn’t be any distinctions on clothing. I just feel like it’s too late to change that.

    • Here is the thing Ernesto…unless you have tried something, you really have no right to critique it. Since you have absolutely no idea what it is like to walk around in a dress all day, your words are simply conjecture. Oh, and I definitely did not dress as a woman, I simply wore a dress. In my flip flops, no make up, no anything (other than a dress) that would suggest I was dressing as a woman…I was very much a man wearing a (very ugly) dress. Perhaps if the mood strikes, I will one day dress as a woman…perhaps even slutting it up with a tight dress, CFM pumps, make up and fake boobies. But, until the mood strikes and the right context presents itself, you will just have to fantasize and use you imagination 😉

  7. I’ve worn dresses my whole life. You are right there are certain times you don’t feel safe! But then I realized that I also don’t notice it sometimes. I have become immune to it. Also I’ve never realized the double standards between men and woman cross dressing. I have a lot a of gay friends and they get looks all the time and it’s sad! But being lesbian is more acceptable. Could it possibly be because men fantasize about 2 women being together? Or possibly because woman are more tender and sometimes woman want to experiment with other woman?

  8. Great blog! You have a typo in the 3rd bullet point “we we”, but, other than that, it was a very interesting read. The first point was obvious to me about how much effort it can take to keep your “junk” covered since I’m a girl, but on the bright side we don’t have to deal with erections.

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