Do I still Fashion Freestyle in 2021?

The above is a list of all the posts I have made to this website since the start of 2015. Six and a half years ago. Going through all my posts I’ve noticed a trend. I tend to post most in June followed by May and March. Despite what it may show in this list above where I have a couple February posts and a January post. So I’m curious what is going through my head in May and June.
It might be the coming of spring. Where I live, we tend to get a late start on spring. We can get a few days in February and March that I call a spring preview, but April tends to still be cold (I think we even got snow this April) or sometimes a mixed bag. This year May has been a mixed bag. We’ve had a nice week followed by a cold week and are now back into nice again, even hot. So I think May is really where the weather starts to turn. I think that mentally I must spring open myself. Flower if you will. Just a guess. Although it doesn’t appear to last long since I then fail to write anything in July or August most years.

But let’s look closer at that list. I actually don’t write anything most years. Two posts in 2015 on the same day and then essentially two years until my next post. Five months later in May I post again, then another three years almost (two months shy of it anyway) until my next post. Three years! To be fair I did attempt a post in March of 2016, but only saved it as a draft. I also did two additional draft posts in 2017, once in January and in June. So the idea is that I was still coming here from time to time and attempting to write something. Still, it’s not often, with huge multi-year breaks in-between. And now over a year later I am posting again since my last post in March of 2020. And I certainly had some time in 2020 with the Covid19 lockdown to write some posts. So what is going on?

The truth is, since 2015 I’ve slowed down on the fashion freestyle lifestyle tremendously. The height of it was kind of a phase for me. One that seemed to span from my late twenties to my mid thirties and began tapering off quickly in my late thirties. I’m not entirely sure why this phase happened. The reasons that might contribute that do spring to mind are kind of personal and I’m not sure I want to share them here. Even then, I can’t be 100% sure of those, they might have contributed.

I’m certainly not against freestyle fashion. It’s not as if I did a complete one-eighty. I think two things happened to change my perspective though.

The first and most important is that I got older. I hit my late thirties and early forties and I began to feel less attractive. I had put on some weight and was self-conscious of my body on one hand, while on the other the extra weight made me feel a bit more manly. I’ve always been taller and what I would consider average in weight, but now I felt a bit stocky and burly and that wasn’t jiving with my conception of myself as a freestyler wearing panties and a skirt. Combined that with the fact that most of my female clothing that I bought for myself didn’t fit anymore, and well, I just let go of much of it.

Now, I did say it tapered off. It wasn’t as if I stopped completely. There are times you can still find me lounging around the house in a long skirt or a pair of leggings and a t-shirt. And the panties are still part of my underwear drawer and regularly cycled in with my boxer briefs and mens bikini briefs. Even up to right now. So technically, actively, I’m still a freestyler. But I haven’t bought anything new that is sold-for-females in years and I mostly skew toward my sold-for-male clothing when it comes to putting something on. In fact most days if you caught me you would find me in a pair of mens jeans or shorts, mens socks, boxer briefs, and a t-shirt or button up shirt. Maybe a flannel or a sweater. Stereotypical male.

Of course none of that goes against the freestyler ethos, which is to dress how you want to dress despite the sex the clothing was sold-for. Which is not to say that every male dressing in stereotypical sold-for-male clothing is a freestyler who is just choosing to dress male.
To actually be a freestyler, you have to cross that sold-for line and wear something that was sold-for the opposite sex at some point. And not as a gag, or costume on Halloween, or as part of an act in a show. Otherwise you’re just a stereotypical male dressing as a stereotypical male.

I also don’t think it’s unheard of to consider phases in ones life. The idea that for a period of time, be it a day or a decade, one might drop in or out of the fashion freestyle lifestyle. That it may ebb and flow. That you may find yourself at different degrees of it.

For the last four or five years I just happened to find myself at a point where I freestyle mostly in the form of panties and leggings around the house. With the occasional skirt around the house if I want a freer feel. I’m not wearing women’s jeans or tops anymore. You aren’t going to find me in bright pink or frilly things. Most of my panties even are just basic briefs, some are even more masculine looking in camouflage. They are hardly all that different than mens bikini briefs.The leggings or skirts I wear are plain and black. Hardly eventful or overtly feminine aside from the fact they are leggings or skirts. So it could also be that I just found my new vibe and it’s not all that feminine and skews more masculine overall.

So what was the second thing that happened?
I think that as I got older I became less adamant that other people accept my fashion choices and change their overall perspective. This was in many ways my social cause. I was flying the flag and waving it around trying to convince other people that they were seeing things wrong. Much to the chagrin of my friends on facebook who were dealing with me as graciously as they could, while I soldiered on in my efforts to change the world.

Today I’m wiser and less insufferable. At least in that regard. lol

I tend to just live and let live now. I don’t push the issues, I don’t even bring it up anymore. That’s true of not just freestyle fashion but other slightly controversial issues I had been passionate about (religion and politics). I just came to accept that most people don’t see it the way I do and never will. It’s not their thing, so they have no reason to.

The world is large and complex and if the internet has taught us anything, it’s that people have all kinds of niche interests and passions that don’t fit the larger mold of society. And maybe they shouldn’t. Even if we often, passionately, feel like they should. But I may also feel that way because I am less outwardly freestyle appearing. Like I said, I tend to just wear panties or lounge around the house in leggings or a skirt as my freestyle expression. I’m not pushing the same boundaries I might have been in my early thirties. So I don’t feel the same pressure I might have then to try and change the world.

But it’s also possible my style changed as a result of pressure from the outside world to conform. That as I got older I began to feel more out of place being outwardly freestyle appearing.
In some ways it was perhaps clashing with my interests in running a business and being taken seriously by the others I do business. Or just people I interact with in society as a whole in my daily life. There is truth in that.
Also on some level, I started to feel like that flat assed beer bellied old guy in a thong speedo at the beach that nobody wants to see. Instead of feeling like I was young, sexy, and free.
But I also just grew up more. I realized that I have a duty to society, and my family, to be a part of this society and not just stand opposed to it like some child stomping his feet and demanding it change to suit his desires.
It’s ok to have your passions, interests and desires and it’s ok to inform the world about them. But it’s another thing to bitterly demand the world change to accept them as part of mainstream society.

I think another thing I learned is that sometimes it’s better if these things aren’t mainstream. The entire world doesn’t have to be on board with what you’re into. So long as it’s not illegal, you might find better company is a smaller niche group that are also just as passionate about it as you are. In a way, it keeps it exciting and exclusive and can make you feel like you belong to a community.

That said, that never really happened with the fashion freestyle movement. You can’t even call it a movement. This entire time I feel like I’ve been out on my own. Just this website and a few readers that drop in every once in a blue moon and maybe leave a comment. Even then, they have given me no indication that they are freestylers themselves. So I often just assume they are cross dressers that somehow came upon my site here and then moved on to actual cross dressing content elsewhere.

If anything I’ve felt like a niche within a niche. Freestyler would be regarded by the greater public as cross dressing since they don’t know any better and don’t care. Yet at the same time the cross dressing niche is not the same thing. They have their own goals and do their own thing, which typically is to present as the opposite sex. As an expression of their inner opposite sex persona. So a fashion freestyler barely fits in there since fashion freestyle is really more about fashion and not about gender expression. Or at least not to the extreme it is for cross dressers.
If anything, fashion freestyle is like the bisexual of the LGBT community. It’s there, but if noticed at all, it’s seen as a gateway to full-on homosexuality for men. Like the bisexual is just sitting on the fence, scared to jump down to the other side. And much like the bisexual female, freestyle fashion is more accepted for women than men.

So where does that leave things?
Well, I had started writing a post titled The Last Freestyler in June of 2017. It was about shutting this website down. I saved it as a draft and never posted it. It started like this:

While I’m faced with having to renew this domain name for another year (and I probably will because I’ve learned my lesson in the past) I have to ask myself if it’s ultimately worth it.

The truth is, I’ve taken up this fight to help educate people on the logic of the fashion freestyle philosophy. A concept based on personal preference and freedom in what you wear. Crossing department lines to carve out your own niche wardrobe based on what you like, rather than how society tells you to dress based on what is between your legs. Always seemed a noble cause to me. But the truth is, most people don’t care. They’re perfectly happy with these divisions and will argue to keep things divided.

Soon enough I’m faced with the same choice again, to renew this domain name, in June. Maybe that’s why I post in June more than other months. I get the notification for renewal and come back here again to reassess whether or not it’s worth keeping this website going and end up posting.
Well, I do plan to renew again this year and keep the site up. If for no other reason than that fact that I’ve lost plenty of domain names in the past that I’ve later regretted losing, only to discover that some domain squatter picked them up and now wants thousands of dollars for them. The reason, because I used them just enough to get them listed somewhere on Google. So I guess they apparently have more value as a result.
Plus this site is hosted on a plan with a few of my other websites that I need to keep going. So it doesn’t cost me anything extra every month to keep it around. Just the ten bucks a year or whatever to renew the domain name.

Still I sometimes feel bad keeping it around considering I’ve barely visited it myself over the last five to six years. But do come back eventually, and at the very least it’s a record of a piece of my past even if my tune has changed on it a bit.

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  1. Welcome back! I must confess I stopped making a regular habit of visiting your site after I saw no updates for over a year.

    I also have gone through some time of introspection as I read more from other men who continue to identify and present as men whilst wearing clothes from “across the aisle”. Only in the last few years has the concept of “gender non-conforming” taken hold in mainstream conversation, and it is so much a better fit for me than “crossdresser”*. I am all man, inside and out, only I colour outside the lines. Society says men can’t wear certain clothes or exhibit certain behaviours, and if you do you aren’t a man. And yet… here I am. Not sissy**, not “gurl”, not “boi” or trans-anything, just good old Ralph rocking his Lindy Bop 50’s style maxi dress.

    * I don’t object to the term. I do, after all, wear clothes meant for the opposite sex which is technically all “crossdresser” means regardless of motive or identity. But most people add a lot of other baggage to the term and assume if you are a crossdresser you also desire to be a woman, for some or all of the time, so I don’t identify myself as such.
    ** Nice article on the sissy culture, by the way! I quickly drop out of social media forums related to crossdressing when that becomes the focus of participants. But I’ll revisit your 2020 article and add more comments there.

    1. Thanks for the complement about the 2020 article. I just reread it myself. It’s been a while. Although it’s kind of sad we can refer to it as the 2020 article, since it was the only one written that year. lol
      I really need to write here more often.

      You’re right that the term crossdresser is loaded and internet culture has turned that up to 11 with all the sub-terms that go along with it (like gurl). Plus redefined the term sissy, as you mentioned in your other comment. I also remember when that meant something else.

      Gender non-conforming is a good term. Although when I hear that I tend to think of someone who views their personality as more neutral, and not just their sense of fashion. Although I could be wrong.

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