In the article titled Rubberband Boundaries I touched on transvestites and their full bravado toward the princess zone of the feminine side. Truth be told many don’t go full princess. Many stop at the lace and latex shop and skip the pink because what they’re after is sexual fetish more than pure likability. I don’t mean to downgrade this style of crossdresser by saying they don’t like what they’re wearing or doing. Of course they like it. But they tend to like it from a sexual fetish perspective.
In a milder zone there are the crossdressers that go full fem with wigs and high heels blazin’. Resistence resistence, resistence. Their goal is passability. Many don’t realize they wouldn’t come a million miles within the passable zone. But they think they do. Yikes!
The problem here is that they get us casual crossdressers pegged as freaks. We aren’t trying to be passable. Hell we aren’t even trying to be female. Best we’re shooting for is an expression of our feminine side. Even then some of us would say “screw that! I’m a dude who just likes pink dresses. It has nothing to do with expressing a feminine side.”
But this is a difference between practical and gawdy. The reality is, mens wear is designed to be practical. What we define as feminine in our society is often less practical and more pretty. If you think about it, there are reasons for this. Men historically have been workers out in the fields and factories. We’ve been on the front lines of war, rescue and the hunt. We haven’t had a ton of time to be pretty. Our waredrobe has been designed to optimize our effeciency at whatever it is we’re doing so that we can be the bread winner.
Females on the other hand have historically been mothers and homemakers. Their goal was to secure a man who could take care of them, create a family with them and provide for them and their family. As a result they’ve gussied themselves up in multiple ways over the ages.
So it’s really no surprise that as females have gained equal rights and greater job opportunies, they’ve had to take on male waredrobe. Afterall that is the time tested, most practical and efficient waredrobe for the new jobs they’ve earned. And just like the male work waredrobe trickled down into casual everyday wear (think denium & t-shirts) the same has happened with the male-cum-female work waredrobe. But over the decades it has gotten the addition of female flare in the form of tighter fit, gems/jewels elegant embrodiery and various color choices. Ultimately the same rules apply, women are still in the mode to catch men with their looks. Just because we have had a handful of decades promoting feminism doesn’t mean you can throw out thousands of years of evolutionary and societal development in that time alone.
So with that in mind, let’s approach the male side of things. Men who cross dress want to immediately jump into the deep end. As if they are kids in a candy store with an unlimited credit line. But that doesn’t work, because the same rules apply, remember?
Our goal as casual crossdressers is to increase our choices without putting ourselves into the weirdo zone. Because we’re men, we need to hold onto the practicality side of things. Anything that is non-practical gets us called out. Even things that are practical like purses and skirts can get us called out pretty quickly unless we make a practical case for them.
I’ve personally been carrying a purse for almost a year now. It goes with me almost everywhere. I’ve gotten some looks, sure, but never have they been ass kicking looks or complete disdain looks I might get if I were wearing a skirt in a grocery store for instance. Something I’ve also done. But it’s because I’ve done these things that I can tell you what works, what does not work and why.
Rule number one is not to shoot straight to the skirt. This for some odd reason is the most jarring thing a man can do in our western society. Even though technically men have been wearing skirts on this planet far longer than they’ve been wearing pants. Count all the various skirt-like garmets men have worn over the ages. From early Egyptians, Greeks and Romans to the Scottish kilts, the modern middle eastern dishdasha to Americans putting baby boys in dresses as late as the eary twentieth century. Plus countless other cases and cultures in a list to long to name.
But the skirt is the first red flag people peg for cross dressers. So if you’re going to wear a skirt, you’re going to need to man it up quite a bit and prepare it for practicality with a lot of pockets and excuses about chaffing. But let’s skip skirts for now.
We’ll eventually get into some practical outfit demos on this website as we continue along over time. That is one of the goals here is to give you outfit advice by picking out and piecing together outfits you can wear that meet the demands of the casual crossdresser while maintaining the practicality that society deems necessary for mens wear. Until then I’m just trying to cover some basics.
The first and easiest thing you can do is shop the lingerie aisle. This is one quick way of getting some color and choice into your waredrobe. Even though only you and your significant other may ever see it, it’s also for that reason the only area where you can go buck wild and wear whatever suits your fancy. However I would stay away from bras since you more than likely don’t have the goods to fill them and as a result don’t have a need for them. Unless you do.
Another simple option is leggings and pantyhose. These are practical. They help circulation in the legs and provide warmth under your pants during cold months, especially if you live in the north. They aren’t as warm as long johns, but also not as cold as going without anything. So they provide a great middle ground. If you can get them in a variety of colors then go for it. You can wear them under your pants or even under ripped jeans where they can peek out and tease a bit. If you plan on keeping your leg hair, I would recommend getting thicker and/or darker colored leggings that aren’t so sheer. Nobody likes leg hairs poking out of nylons.
Leggings can also be worn with cargo shorts and combat boots during the fall and early spring where it’s still cool enough to merit their use but not winter cold. This is you getting a litter braver with your waredrobe, but still perfectly acceptable if the leggings are thicker and darker/muted in color.
Pink is also fine in patches. Don’t go full princess. But if you find a way to wear pink in patches, go for it. For example I have a pair of sunglasses that have pink arms and a black front. People just think I’m kicking it with the hipster retro 80’s thing, but really I’m expressing my like for the color pink. It isn’t often or in many ways that guys who like pink can wear it successfully. So if you do like it and want to rock it, do it, but do it sparingly and bold against black.
These are just a few examples. But the execution remains the same. You have to be practical to be acceptable. The minute you show up in a yellow ballgown you’ve ruined it. Like it or not, there is still expectations for genders. Hopefully one day these rules won’t apply so much. But until then we’ve got to push boundaries slow and steady if we still want to be accepted as professional and attractive to our significant others. You could go full princess tomorrow but you’ll probably lose your job, your significant other and the respect of people in your community. If you’re a college kid that may not mean much, we kind of expect that out of you already, but if you’re older than 25 it can be a problem.