Men in Heels: Why More Men Are Exploring Crossdressing


ByEnter the fascinating world of crossdressing!


Uncover why more men are slipping into heels and exploring this vibrant facet of self-expression.


Join in!


Let’s step into a world that’s far from black and white.


A world that’s not afraid to blur lines, break norms, and stride confidently into new territories.


Welcome to the realm of crossdressing!


Long considered taboo or misunderstood, crossdressing is having its moment in the spotlight.


More and more men are exploring this high-energy avenue of self-expression.


self expression  


It’s a brave new world we are living in—a world where the binary of male and female is giving way to a spectrum of identities, each as valid and celebrated as the next.


The face of masculinity is evolving, and it’s wearing lipstick, eyeliner, and, yes, a fabulous pair of heels!



Historical Context of Men in Heels Crossdressing




The association of high heels with femininity is a relatively new construct.


In fact, heels were originally designed for men While you chew on that tidbit, let’s rewind to the 10th century, when Persian horsemen used high heels to secure their feet in stirrups.


Fast forward to Europe in the 16th century, and you’d witness men of power strutting about in heels, a symbol of their high status.


Louis XIV of France was quite the trendsetter with his red-heeled shoes.


The higher the heel, the higher the esteem – quite literally!




Crossdressing, too, has a rich history.


The Greeks and Romans had male actors donning female roles in theatre.


In Japan, Onnagata male actors mastered the art of performing female roles in Kabuki theatre.


In each case, the intent was not to parody femininity but to celebrate it.


By the 20th century, heels for men were hidden due to stigmatization.


But now, we are living in a time where men can enjoy heels without it being a punchline.


Isn’t that something to celebrate?


The Modern Perception of Crossdressing




Crossdressing in today’s world is not cloaked in secrecy—it’s being celebrated on catwalks, in the music industry, and on the silver screen.


It’s not just an aesthetic statement, either.


It’s a bold move towards breaking free from society’s definition of “normal” or “usual.”


So, who made the waves to help make these shifts?


Often, they are pop culture icons who are not afraid of defying expectations.


Like who, you ask?


Remember when the legendary David Bowie?


He who threw on a dress for his album cover, The Man Who Sold The World?


He wasn’t just playing with fashion.


Bowie was challenging the norms of gender expression.


Fast forward to today, and we see global superstars like the former 1D singer Harry Styles gracing the cover of Vogue in a stunning Gucci gown in Playtime With Harry Styles.




Then there’s Billy Porter— the king of genderless fashion.


His heavenly tuxedo gown at the 2019 Oscars red carpet?


Undeniably epic.


He wasn’t just making a fashion statement—he was creating a dialogue about gender fluidity.


It’s not just the celebrities!


Even fashion brands themselves are dissolving the gender boundaries.


Remember when heels for men walked down the runway in the Dsquared2 Spring 2017 menswear show?


These influential figures and brands are more than just fashion trendsetters.


They are catalysts for change, advocating a more inclusive society.


They’re not doing it for the shock value.


They’re doing it to illustrate the simple fact that clothing has no gender.


Crossdressing as an Expression of Identity




Let’s dive into the heart of the matter—crossdressing.


For many, it’s an intrinsic mode of self-expression, a special map of one’s identity.


It’s a tangible way to explore, express, and embrace the spectrum of our individuality.


Hannah McKnight: Advice, Fashion, Activism




Hannah McKnight’s personal page is an informative blog you can refer to anytime.


This is especially true if you’re looking into crossdressing.


Here, McKnight recounts her experiences, offering a peep at what it means to be a crossdresser and a trans person.


One of her latest tales is “Sexy Halloween Party.” It chronicles her humorous and candid account of navigating the festive season in heels.


Though it has fun posts, the heart of her blog is its honesty and depth.


One standout piece is the post “Marriage, Crossdressing, and Fantasies.” In this deeply personal piece, she delves into the complexities of her identity.


McKnight shares, “Years ago I identified, a little reluctantly, as a crossdresser.


I wasn’t always super comfortable with the term, especially since there was/is such a perceived sexual stigma largely associated with it.”




She adds her complex thoughts, then and now: “Not that there’s anything wrong with crossdressing being a sexual thing, but this aspect of me was never a kink.


I mean, I described it as such but not because I found it erotic or arousing, but since it was typically framed as a kink, what else could it be?”


Her blog is a must-read, especially for crossdressers who are also wives, providing a reservoir of wisdom, empathy, and understanding.


It’s a testament to the diverse experiences and identities within the crossdressing community.


The Natural Touch: Simone’s Update – Celebrating One Year of Crossdressing




It’s been one whirlwind of a year for Simone. She recently commemorated her first anniversary of being a crossdresser.


She shared this milestone on The Natural Touch, celebrating with a picture of two ladies toasting with bubbling glasses of champagne.




Simone recalls her expectations for the year, then scribbles: “In my last diary entry in February of this year I predicted that 2023 would be full of even more milestones reached and achievements accomplished and so far, with Marion’s unbelievable encouragement, this is turning into a year that out surpasses anything that I could have ever dreamt of.


Simone’s journey has been nothing short of inspirational.


In her update, she recounts the ups and downs and the profound personal growth she experienced (In both crossdressing and eventually transitioning).


Her post was not just a reflection on the past—it’s an eager look towards the future.


JoeyPress: Wearing a Skirt Around My Wife and Having Zoom Calls




JoeyPress is an insightful platform sharing a cornucopia of crossdressing stories and experiences.


One memorable story chronicles the poster’s eventful week in a fascinating day-to-day account, filled with special times and first-time experiences.


He says, “This was a week of special times and some first-time experiences!” His excitement oozes out of the screen into the readers.


On the last day, he shares that his wife was ppreciative of his “dressing nice for her.”


In his account, each day includes not just the fits he picked.


They are more than that—they are his steps toward discovery, acceptance, and realizing the joy of crossdressing.


Most importantly, the week also strengthens the bond between him and his wife, highlighting the beauty of shared acceptance and understanding.


Practical Guidance for Men Exploring Crossdressing




So, as a man, where should you begin your journey into the fabulous world of skirts, heels, and lipsticks? Here’s a handy guide—just for you:


Find clothes you want to wear.


There’s every style and size available for you.


Yes, you’ll be intimidated in your dawning steps, especially if you don’t have anyone to guide you through racks and shelves of fabrics.


But you don’t have to be in a physical store just yet.


Comb through WWW first—there are endless online shops available to you, wherever and whenever.


Don’t forget your local thrift shops either—they are a goldmine for unique, budget-friendly finds.


You just have to brunt the effort.




Selecting the size that fits you is just as crucial (and yes—it can feel like a minefield).


But don’t you worry; size conversion charts exist for a reason!


These tools allow you to convert men’s sizes to women’s (and vice versa!) A quick Google search will link you to an array of these things.


Now comes the “how” of using these clothes—dressing and styling.


For that, watch YouTube channel tutorials.


These channels cover everything from makeup application to walking in heels—for free.


Online forums like Reddit’s r/crossdressing are a treasure trove of information and advice and, perhaps more importantly, a supportive community.






To be in the first blush of your crossdressing adventure means stepping into a bride.


A bridge that will take you to a whole new world—one that doesn’t require you to have any magic carpet, no less!


Let your curiosity get the best of you.


The key to discovering your full identity is just right there, on the other side, waiting.


Remember, though, that like other mediums for self-discovery, crossdressing is not a -size-fits-all approach.


If anything, it’s something that you should tailor to yourself.


Plus, your exploration should be all about expressing your unique style and welcoming who you really are.


So, whether it’s for the first time or the fiftieth, strap on those heels, be bold, and remember to have fun on your journey of self-expression and discovery!


FAQs : Why More Men Are Exploring Crossdressing




What societal changes have influenced the acceptance of men crossdressing?


Societal acceptance of men crossdressing has increased in recent years due to several factors.


The rise of the LGBTQ+ rights movement and more open dialogues about gender and sexuality have led to a greater understanding and acceptance of non-normative gender expressions.


Plus, the concept of fluidity in fashion and the blurring lines between “men’s” and “women’s” clothing in the design world have also played a significant role.


Are there historical figures who crossdressed?


Of course! History is dotted with many who crossdressed.


For instance, the Chevalier d’Éon, an 18th-century French diplomat, lived the latter part of their life as a woman.


In pop culture, the legendary comedian and actor Eddie Izzard has been openly crossdressing for years.


What are some popular misconceptions about men who crossdress?


One common misconception is equating crossdressing with transgender identity or sexual orientation.


While some crossdressers might be transgender or non-binary, others identify as cisgender and may be of any sexual orientation.


Crossdressing is about personal expression and comfort—it doesn’t necessarily indicate one’s gender identity or sexual preference.


Another misconception is that crossdressing is a fetish or kink.


While this can be the case for some, many others crossdress for various reasons, such as self-expression, comfort, or art.


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