Cross-Dressing is Wonderful, and Here's Why

Before we begin, if you’re unaware of what cross-dressing is, it’s essentially wearing clothes that are typical of the opposing sex, so clothes that have been previously defined as more feminine or masculine. Without further ado, please know that this article has the intent to (hopefully) help give reference to the classics that lit the path for cross-dressing, as well as basically to call bullshit to gendering clothing. So, here we go!



  1. 1. A Brief History

    Okay, so cross-dressing started in about early to mid-1800s. I won’t go into all the facts because honestly, it’s quite scattered, but the furthest back example I could find was Harriet Moore, who lived as a “man” for about seven years, after her parents passed and she was forced to work in a less than understanding society, therefore, taking the identity of a male and dressing the role she was forced to take on. Obviously, the idea of cross-dressing has since changed a bit, and I feel lucky enough to live in a time where I can alter my dad’s jeans, add some embroidering and walk around like it’s just another day, but it's taken a long time to get there. Harriet's story is actually a really common one for that era and in other countries, because women who were unable to take "male-held" positions, often had to go well out of their way to make money, more often than not through prostitution or the selling of their bodies. They were honestly incredibly badass, and I hope they somehow know the mark they've made and the progress they helped move forward.

  2. 2. Slowly Getting Normalized

    Friends Excited

    Of course, I needed to mention the impact of public figures and the impact of films, because not only is it my excuse to rant about films, but it’s still incredibly relevant. I mean, I remember watching Friends, and once it was put on Netflix, every single person in my high school had Rachel Green as their favorite fashion icon. And what a brilliant choice she is, because not only is she the perfect segway into my next favorite female icon, but she is the queen of cross-dressing for the 90s. She’s surrounded by powerful company as well, because Jo March, from Little Women, who mind you is a fictional character, empowered women to not only speak for themselves but dress in the clothes that were originally crafted for men. I also wanted to mention the men that have not only normalized the change in male fashion but have encouraged a push towards gender-neutral pieces. Of course, Harry Styles, who has been perfectly ambiguous when it comes to his sexuality and clothing choices. Another being Johnny Depp, as well as Adam Lambert, and many others, all of whom have essentially rejected gender norms and openly spoken of their fashion choices, which I feel is so important. Then, last but certainly in no way least, Katherine Hepburn, a.k.a. the woman that normalized women wearing pants. She was considered too head-strong of an actress, that directors avoided casting her, especially in romance films, because they wanted her to be more submissive and “less masculine.” It brings me so much genuine joy to think that something as minuscule sounding as pants sent people into a spiral, thus leading to a massive change in female fashion and empowerment.

  3. 3. Why Cross-Dressing Is So Freaking Cool

    Fashionista Article Rep Image

    I mean, if you think about it, it’s truly another form of self-expression, like why we dye our hair or wear two-different socks instead of a matching pair. I love films that highlight clothing as a personality trait, because it truly is, even if you’re just wearing some khakis and a polo shirt. That could be your favorite polo because it feels warm and pre-worn every time you wear it. Or maybe you’re more of a rainbow jacket kind of person! Whatever makes you happy, I really hope you get the chance to wear it and express all your joy. I love the idea that clothing is an unlimited idea. Like 100 years ago, no one was looking at certain fabrics or trims because they were too “gender-specific.”

  4. 4. When is it Time to Try it?

    Denim Jean Jacket Wink Patches Eyes

    Obviously, there’s no specific answer to this, however, I wanted to mention it because I remember it took me about a year after coming into possession of my dad’s old jeans before I decided to even alter them, then another few months before I got up the guts to cut them into shorts and wear them in public. I would love to say I was always a really gutsy kid that said no to gender norms, however, I’m also really self-conscious and fearful of literally anyone critiquing me at any point of the day. Which is stupid, because no one has ever (or likely ever will) come up to me and just say “hey, that looks stupid.” No one does that, and honestly, more often than not, people will think it’s cool that you’re experimenting with fashion. If they do, that just means they’re too self-conscious themselves anyway.

     It sounds cheesy, but the moment you realize you can wear literally anything that makes you happy, it entirely changes the game. I used to have this pair of shorts from American Eagle that looked fairly 90s grunge-inspired with drawings and quotes written all over them, and I got so many compliments on them! I remember it took me four months before I wore those to school. That’s four months of me being too insecure about something that could’ve given me so much joy and self-expression. Clothes weren’t made to limit people into boxes of insecurity and self-consciousness. If anything, they were created to make people feel good and content and be put into a positive mindset before they do any of the things they have to do. I don’t know if this is a personal thing or not, but whenever I wear an outfit I feel cute in, it makes my day better. Like if I got 54% on a quiz while I was wearing the clothes that I slept in, of course I’m going to feel pretty bad, however, if I’m wearing my favorite heart-covered turtleneck (this is my actual favorite shirt, by the way) and my best altered Levi jeans, it’s a good day to get an F! 

    My point is, there is no specific moment to begin experimenting with fashion. It took me years and stages of “testing” brands and styles and “gendered pieces” before I realized what I liked and what I didn’t. I tend to like a mix of both, and that says absolutely nothing about my gender, nor should it. Whether I want to wear a skirt and a star-covered button up or my parents' old coat with my favorite mom jeans, as long as I feel good, that’s all I’m going to care about. Clothing isn’t a straight line, and I hope it’s something that never ends.

If you were looking for a sign to wear that piece of clothing that’s been sitting in your closet, waiting to be worn, this is it! I love the impact clothing can have on a person, either emotionally, physically, or mentally, it can really help in a lot of ways, and I hope that’s the takeaway you got from it! You’re never too old, too young, not skinny enough, not thick enough, or literally anything else to be “limited” or “not right” for a piece of fabric, so go out there and express yourself in all your outrageously lovable pieces of uniqueness!