Skirting The Issue - Helping Men Feel Comfortable Wearing Women's Clothing

Seller Sellers’ Perspective
Skirting The Issue - Helping Men Feel Comfortable Wearing Women's Clothing

I could tell how stressed of a day my dance partner had by his duffel bag when he came over to do laundry. The harder the day, the more likely his bag would be stuffed with a pair of heels with his makeshift little black dress. To me, his raids on my closet were no different than me claiming one of his sweatshirts at work.

My dance partner, Joey*, is athletic and built like a basketball player. His long limbs, broad shoulders and built legs can command a stage or keep up with the heavy lifting production grips. Joey is also sensitive, smart, and soft-spoken. Effeminate in ways that irritated one of his family members to the point of throwing out all of his dance gear when found taking dance classes in college. His compassion shows through in his caring nature and infectious laughter. But the feeling of insecurity he carries is evident when he pauses, looking around before touching a woman’s garment rack during one of our public shopping sprees.

It wasn’t something that my dance partner hid from me. With both of us working in the performing arts, it was just another day at the office. Seeing a man strutting in a pair of 5-inch heels or posing in the mirror wearing a dress with full makeup wasn’t shocking or taboo.

When Joey‘s last girlfriend found his stash of items, it was too much for her. Up to that point, his play wardrobe consisted of a makeshift one size fits all tulle skirt, a second hand little black dress, some panties, and two pairs of heels that he had collected. She was not OK with it. Not in public and not in private. She was worried that he was possibly transgender, gay or as she put it, “living some Eyes Wide Shut lifestyle”. Labelling him a sexual deviant and me an enabler, the decision to out him to his and her respected families was damaging.

This confrontation set both of us on intertwined paths of self-discovery. For him, his path was to figure out what it meant to him and his life. It sent me searching for options and understanding of how I could be more supportive of him and thus help others.

I started reading blogs, websites, support groups and anything I could find. I started researching clothing, measurements, how tailoring was done, designers, DIY and sizing. I was very saddened by the somewhat limited resources for men but honestly how gender/social norms and clothing is defined.

Finding Options - Discovering All Things Worn

Sites like ATW have dramatically helped in finding items but, it is still complicated at best. For some, it’s all about identifying with the clothes, while others it’s sexually arousing or comforting. There are so many reasons and different facets of this that one discussion doesn’t even skim the surface. Not every man that likes feminine women’s clothing is a sissy or wants to be hardcore humiliated. Nor is every man that wears panties or bras contemplating unresolved issues with his sexuality. There is no “one” answer to this, as it’s specific to the individual. The biggest difference many times is the deeply personal motivation behind it.


As many women can attest, our sizing system is broken. It has been broken for many years. Standardized sizing hasn’t been seriously updated since the 1960s. The measurements taken then were only taken from one demographic. Women’s bodies and shapes are ever-changing. Literally, you can have 2 women that fit the same designated size but their bodies can be totally different. Vanity sizing is a problem too. Vanity sizing was devised by the fashion industry to make women feel better about buying clothing. Clothing all the way down to panties are made to straddle between 2-4 sizes. Body scanners, both within the US and abroad, are being used to take accurate, up-to-date readings for sizing. However, again no commercial standard exists, and manufacturers are free to determine their own sizes. Heaven help you if you are curvy. And don’t get me started on the one size fits all/most sizing.

Why Does it Matter? The Sliding Scale

All of this makes it difficult for men to do a proper exchange as most use a formula using a woman’s standard size as the basis. Men’s sizes are largely based on combinations of chest, waist and leg measurements. A woman’s size 12 at one store can be astronomically different by another manufacturer. Men’s necks, arms and chests can all be broader or wider. They can be taller in stature with less defined curvatures giving clothing a more boxey or flat appearance when worn. Have you ever seen someone list a specific manufacturer in their profile regarding clothing...they might not be trying to be difficult but rather they have found that this is the best one that fits them so far. Giving measurements along with whatever size is on the tag/written can help buyers in some cases.

Creating Options

Whether it is when I create an original, build a piece from a mass-produced manufacturer’s design, or look for pieces that I can add to my shop, I try to give real options to the buyer. Maybe they would like a more open design on the sleeves or a more rounded boat neck so it’s not as tight. I give a little more in the midsection or use materials with more stretch as panels. Gloves are tested for sizing before I put them up for purchase. Accessories are tried. These simple things can make a world of difference to a fit. Whatever the idea, I try to make something more functional for them.

In a time when acceptance and mental health is paramount, there is a greater meaning than what some might think on first glance of a site like ATW. I’ve made rhinestone panties for construction workers and ballet tutus for attorneys. I’ve blinged out used shoes and made sequin stripe leggings for baseball players. And I’ve made a proper little black dress just for Joey.

With Joey’s blessing he’s pushed me to write this in hopes to help others. To me, it is all worth it when I hear back from someone and how it has helped them so much. In the end, I know it allows others some kind of balance. Call what you like. All I know is it’s something that has saved my friend Joey and countless others. It’s something he likes to do and is part of him, bringing balance to his life, and keeps him centered and sane. That’s all I could ask for.

*Joey is a pseudo name.

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