The Issue of Gender and Clothing

Discussion of fashion elements and looks that are traditionally considered somewhat "femme" but are presented in a masculine context. This is NOT about transvestism or crossdressing.

The Issue of Gender and Clothing

Postby JeffB1959 » Sun Feb 11, 2018 10:48 am

Here's a question: Why would a normal, red blooded, middle aged American male like myself choose to challenge and flaunt the conventions of gender and clothing by traipsing about in public garbed in women's wear? Short answer: Because I like to, plain and simple. These days, I consider it incredibly liberating to cast off the shackles of what I'm expected to look like and present the image that I enjoy instead. Society as a whole demands I dress like a man which, frankly speaking, is dull, boring and usually colorless, that said, it wasn't until I started wearing high heeled shoes as a personal fashion statement that I came to understand that there were alternatives to the staid and dismal essence of men's clothing, and how that would eventually lead to my thumbing my nose at societal norms from a sartorial standpoint.

This form of nose thumbing is what I, and others call “fashion freestyling”, the concerted effort by males, young and old to defy gender expectations when it comes to garments and collectively say, “I'll wear the clothes I want to wear, the clothes I like to wear, and if those clothes come from the women's side of the store, hey, that's how I roll.” And why not? There's no laws on the books that says men can't wear skirts, dresses and high heels, women have worn men's clothes and shoes for decades and no one has said squat, well, I believe the tide has turned to say the least. When I first started wearing heels in public years ago, I had absolutely no idea that would lead to where I'm at today, how I've evolved to where I live for and love wearing women's clothing from head to toe, it's as natural to me as breathing, and yes, I won't deny that I look damn good in a pencil skirt and a pair of heels, a key reason why I enjoy doing what I do as it's intoxicating and at times irresistible. Now, I fully understand that not every man can rock a miniskirt and high heels like I can, nor would I recommend adopting the freestyler’s lifestyle, especially not to the levels I have, but for those who have embraced it, like myself, it's opened up a whole new world where the only limitations on what you want to wear exist in your own mind.

Everyone here knows my personal motto which is my signature, “I don't want to LOOK like a woman, I just want to DRESS like a woman”. I live my motto to the one hundred and ten percent fullest because it is very important to me as a freestyler to look nothing less than my absolute best when out in public, to present a tasteful and presentable image when out in public. I've come to enjoy blurring the lines when it comes to clothing and gender by wearing women's clothes AS A MAN, I feel that's it's vital to question why men have to be so annoyingly limited when it comes to what they can wear while women have no limits whatsoever, something I find to be glaringly unfair. Another reason I've adopted the life of freestyler could be summed up in one word, vanity, the simple fact that I look better in women's clothes than I do in men's, and I wear skirts and dresses whenever I can because I love how I look in such clothing. I take an enormous amount of pride in being part of a unique fraternity of men who push the envelope by challenging gender norms when it comes to clothing, we boldly pull on skirts, slide our feet into heels and say, “Here we are, world! Deal with it!” And I'm having a hell of a good time as a freestyler.
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Issue of Gender and Clothing

Postby skirtyscot » Sun Feb 11, 2018 10:55 am

Well said, Jeff! I couldn't have put it better myself.
Keep on skirting,

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Re: The Issue of Gender and Clothing

Postby Fred in Skirts » Sun Feb 11, 2018 6:57 pm

:rock:
Well said Jeff! I too want to wear clothes that are not made for men and I do for the same reason you do to an extant. I think men should be able to wear anything they want and anywhere they want, anytime they want. While I don't wear women's shoes ( only because I can't find any that fit) I would if I could.
Keep up the good work and "Skirt ON".

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:whistle: Hi I am Fred and I wear skirts all of the time. :hooray:
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Re: The Issue of Gender and Clothing

Postby Charlie » Sun Feb 11, 2018 7:28 pm

JeffB1959 wrote:... I feel that's it's vital to question why men have to be so annoyingly limited when it comes to what they can wear while women have no limits whatsoever, something I find to be glaringly unfair.

Maybe my thinking is muddled here, but to me this is a form of inequality. We hear an awful lot about women getting equality with men, and nothing about men getting equality with women; equality is a two-way street. I know that equality in clothing is pretty trivial compared with other forms of inequality (equal pay for example), but I do think it is a form of inequality. Consciously or unconsciously, Cafe members and others are trying to re-dress :D the balance by making a choice to wear clothing not commonly associated (yet!) with men.
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If I want to dress like a woman, I'll wear blue jeans.
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Re: The Issue of Gender and Clothing

Postby oldsalt1 » Sun Feb 11, 2018 7:51 pm

Jeff you have 3 short paragraphs that say a hell of a lot.

I think you presented it very well.

I am by no means a fashion plate but I feel I look better in a skirt than in pants a couple of days ago I posted two photos on the café basically the same outfit the only difference was one I wore a skirt ant the other pants. I felt I looked better in the skirt and a few of the members agreed.

Maybe its because we pay more attention to how we look when we go out dressed a little differently.

I hope you are right that the trend is changing and men will get more freedom in what they wear.

Its funny most of us used to just slop on a pair of pants and a shirt and head out. Now we take the time to make sure everything coordinates and fits better and I think we all have a good time doing it . I know I do.
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Re: The Issue of Gender and Clothing

Postby Freedomforall » Sun Feb 11, 2018 8:18 pm

Very well said Jeff. Your comments need to be posted to capture the attention of the world.
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Re: The Issue of Gender and Clothing

Postby JeffB1959 » Sun Feb 11, 2018 9:41 pm

Thanks for the comments, everyone.

Charlie: Redressing inequality when it comes to gender and clothing is an issue I feel is important since my eyes and mind were opened to how the clothes people wear shouldn’t be limited to the number of chromosomes a person possesses. If a woman wants to wear a flannel shirt, jeans and Doc Maartens, that’s her prerogative, and if a man wants to wear a dress and high heels, that should be his prerogative. Neither should be derided or feel any sort of shame or humiliation for their clothing choices, both genders should be allowed to dress as they see fit, not as society demands, at the end of the day, I just want to see an even playing field when it comes to gender and clothing.

oldsalt1: If there’s one reason I spend so much time prepping for outings and pay so much attention to the clothes I wear and how I wear same all boils down to one reason....I don’t want to be seen as looking clownish, outlandish or embarrassing. To some people, the sight of a man in a skirt and heels is bizarre enough because clothing is tied to gender, to look garish or inappropriate not only reinforces that misguided belief, it magnifies same. I want to look nothing short than my very best, regardless of if I’m in casual attire or dressed to the nines, when I look good, I feel good, plain and simple.
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Issue of Gender and Clothing

Postby Gordon » Sun Feb 11, 2018 10:21 pm

Well said Jeff. I dont have the gift that you have to write like that. So thank you.
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Re: The Issue of Gender and Clothing

Postby Kirbstone » Mon Feb 12, 2018 12:14 am

Not only do you dress elegantly, Jeff, but I'm also a fan of your elegant prose, too. Your recent posts here have a Caerarian impact of the 'Friends Romans and Countrymen' stature. Perhaps you should run for President!

Caesar didn't wear trousers either!

Tom
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Re: The Issue of Gender and Clothing

Postby JeffB1959 » Mon Feb 12, 2018 11:39 pm

Gordon: Thanks for the kind words. I do as best I can when it comes to writing.

Kirbstone: It’s nice to know folks like you appreciate my writing. As for my being a Caesar, I’ll pass, I prefer to keep my back free of sharp implements. :lol:
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Issue of Gender and Clothing

Postby crfriend » Mon Feb 12, 2018 11:53 pm

JeffB1959 wrote:It’s nice to know folks like you appreciate my writing. As for my being a Caesar, I’ll pass, I prefer to keep my back free of sharp implements. :lol:

A well-written sequence of thought is frequently a thing of beauty, and should be so admired. I try my level best when I'm composing, and sometimes get it right and sometimes fluff it. As far as sharp implements applied to one's back, I sadly know those quite well, having had a few figuratively rammed home.
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Re: The Issue of Gender and Clothing

Postby moonshadow » Tue Feb 13, 2018 1:45 am

Very nice Jeff! Your post, photographs and lifestyle is to be admired!

JeffB1959 wrote:There's no laws on the books that says men can't wear skirts, dresses and high heels, women have worn men's clothes and shoes for decades and no one has said squat, well, I believe the tide has turned to say the least.


Not too awfully long ago... it was illegal in many states and communities. I recall reading a post from an actual crossdresser who used to crossdress back in the day (the 60's and 70's I would assume) in West Virginia. She said she always had to carry a men's sock in her purse because that was the loophole if she got stopped by the cops. Apparently as long as you were wearing something (anything) from your assigned[0] gender, you were in compliance with crossdressing laws. Thankfully those days seem to be behind us now.
Everyone here knows my personal motto which is my signature, “I don't want to LOOK like a woman, I just want to DRESS like a woman”. I live my motto to the one hundred and ten percent fullest because it is very important to me as a freestyler to look nothing less than my absolute best when out in public, to present a tasteful and presentable image when out in public.


An admirable comment, however in my personal practice, I do tend to differ to a degree. I agree that I won't want to look like a woman, but I also don't care to dress like a woman either. I simply want to dress like me (Moon Shadow). Now this comes down to our slightly differing styles, and is not meant to say that my way is better than yours, or vice versa. Actually I think you are very well dressed. Some of my skirts are pretty femme, certainly, and I'll throw a fashion curve ball in there and pair them with my old sneakers, or in the case of this weekend's attire, a unisex Macabi with men's tee shirt (for working in). Just whatever Moon Shadow is in the mood for that particular day. It's what makes all of us, even among make skirt wearers, unique! :D

Charlie wrote:Maybe my thinking is muddled here, but to me this is a form of inequality.

Inequality as far as certain employers, and certain spouses, but generally speaking, as is stated above, there is no law prohibiting a man from dressing in a skirt, dress, blouse, heels, makeup, etc, thus legally, there is no inequality. In so far as employers and spouses go, the man is seldom trapped, other jobs can be had, as well as other wives should the man choose to go that route... the choice is his, but he DOES have the choice... But you won't get arrested, or charged with a crime, or locked up for wearing a skirt.

We chisel away at the employers and objecting spouses by continuing to don our skirts and other "women's" attire freely and openly while identifying as the men we are, eventually it may become as commonplace as women who wear trousers.

Many of us here are leading the way into that future!

[0] I've about come to conclude, sex is assigned by the creator (God/Nature/random chance/etc), gender is assigned by human society and culture.
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Re: The Issue of Gender and Clothing

Postby JeffB1959 » Wed Feb 14, 2018 9:51 am

moonshadow wrote:Very nice Jeff! Your post, photographs and lifestyle is to be admired!


Thanks! I do as best I can, and have fun along the way!

moonshadow wrote:An admirable comment, however in my personal practice, I do tend to differ to a degree. I agree that I won't want to look like a woman, but I also don't care to dress like a woman either. I simply want to dress like me (Moon Shadow). Now this comes down to our slightly differing styles, and is not meant to say that my way is better than yours, or vice versa. Actually I think you are very well dressed. Some of my skirts are pretty femme, certainly, and I'll throw a fashion curve ball in there and pair them with my old sneakers, or in the case of this weekend's attire, a unisex Macabi with men's tee shirt (for working in). Just whatever Moon Shadow is in the mood for that particular day. It's what makes all of us, even among make skirt wearers, unique! :D


Admirable comments, Moon. I fully agree that each and every one of us should go our own way, blaze our own path when it comes to our unique passion, that's what makes our little society so dynamic. I don't mind admitting I tend to obsess over my appearance whenever I'm out in public because wearing women's clothes makes me feel special and I want to look special as well.
I don't want to LOOK like a woman, I just want to DRESS like a woman.
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Re: The Issue of Gender and Clothing

Postby Feeling freedom » Fri Feb 16, 2018 1:49 pm

I like what you said Jeff. I too have a great sense of style and I want to express it in my skirts. I would wear my skirts and tights at home, look great and then took them off to go out. While I was out many times I would see an awesome outfit on a women and felt envious because I could not get the courage to show mine off too. Now I go out and strut my stuff in my skirts and it is LIBERATING! My personal style is conservative and non-provocative and I enjoy having that great pair of quality tights or pantyhose, skirt and riding boots that I was envious of on me. No more envy or wishing, only doing. I played competitive soccer most of my life and have been told I have amazing looking legs, it is exhilarating to show them off in a great pair of tights or pantyhose. I am very hairless so I have no leg hairs to shave which is a bonus! I like all my cloths from designers like Robert Graham, Buggacci, Hugo Boss, Kalvin Klein, Ralph Lauren and a few others since they are not afraid of colour and are amazing designers but the most of the rest of "men's" clothing is dull.

It is a lot of fun "freestyling" now and one day I will figure out how to put pics on this web site so I can share my personal style with everyone on this site too.
Personal style is important to me. Even when my outfits may contain skirts, tights and great ankle or riding length boots! I enjoy fashion and am excited to get in on the conversations with the like minded!
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Re: The Issue of Gender and Clothing

Postby skirtingtheissue » Sat Feb 17, 2018 5:56 am

Jeff, You say so well a lot of what I feel! Well done.

moonshadow wrote:We chisel away at the employers and objecting spouses by continuing to don our skirts and other "women's" attire freely and openly while identifying as the men we are, eventually it may become as commonplace as women who wear trousers.

Moon, this chiseling is what it's all about, whether it be skirting or freestyling! That is, without your specific focus of employers and spouses, i.e. "We chisel away at society's "norms" by continuing to don our skirts and other "women's" attire freely and openly while identifying as the men we are, eventually it may become as commonplace as women who wear trousers." Keep on chiseling, everyone!
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