The Issue of Gender and Clothing

[JeffB]

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, 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 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 that 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.

[CAT]

8 hours ago, JeffB said:

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, 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 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 that 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.

Very well said Jeff'!!!!  And you do look fab all the time!!!!

[pebblesf]

You guys are amazing, and do a great job of showing that societal norms are idiotic.  Men with well toned bodies can look amazing powerful and alluring in fem gear, I think their masculinity is magnified as well.   I don't mind admitting I am very envious, but I know you guys have worked hard at keeping your bodies well toned so you surely deserve the rewards that go with it.   

[Pierre1961]

I personally don't want to dress or look as a woman. I am a straight guy who wants to dress as I feel the best  

That means for me: extreme heels,tight waist and often but not necessarily skinny jeans. 

I must be very careful with the food and  have move my old( have a guess ) body regularly  

I feel better than ever and don't wish to go back anymore to strick men's wear. What I have to do sometimes. Unfortunately  

Pierre 

[Shyheels]

I have no interest whatsoever in wearing women's clothing, but I do find the extraordinarily  limited colour choices for men - invariably drab shades as well  - to be annoying, confining and patronising. 

Edited September 19, 2017 by Shyheels

[Cali]

I wear many different types of women's  clothes that I blend with my male clothes and present as male.  There are just somethings, like sleeveless turtlenecks, that men don't have access to in male fashion.  Other items fit better than the corresponding male items, and I have greater color choices.

It's just a matter of time until yoga pants and legging will become standard male clothing. The line between what's male/female in running gear and other sport gear is burring this line.

[Shyheels]

As regards sporting gear I could detect no blurring of lines - certainly not as far as colours are concerned. I was shopping for outdoors (Goretex) parkas with my wife and daughters. The men's colour selection was limited to a very ordinary standard shade of red, a standard shade of dark blue or black.  

Edited September 20, 2017 by Shyheels

[Pierre1961]

Hello everybody !  The shoes of the day: Fuss 17cms no platform. 

[CAT]

Those heels are sweet!

Edited September 20, 2017 by CAT

[CAT]

I have a ton of leggings from Lululemon Nike Alo. Probably 70 plus pairs.   Mostly all Lulu and overall 10 pairs are men's.   I am in leggings all the time not just the gym but running around all weekend.  At home. Going out to dinner(when I'm not in a skirt!).  Leggings are so much more comfortable then jeans.  But my women's 7 For All Mankind are pretty dam comfy too!!

[CAT]

I have yet to post many pics with leggings.  I always end up wearing a skirt!

Edited September 20, 2017 by CAT

[Shyheels]

My only leggings are cycling ones - thermal tights for autumn, spring and winter. And in those, black seems to be de rigueur for both sexes!

[Thighmax]

I have ventured into buying women's clothing and I can honestly tell you that I love the experience.  I now have spanx leggings, dresses, jumpsuits and skirts.  I love how everything feels.  I still don't have the courage to wear them outside though.  I love the way this type of clothing feels, I know that it is what I like to wear.  

[jeremy1986]

@JeffB- that's a great attitude and I applaud you for being so upfront and proud about it.

As you say, not everyone is in the same situation, and certainly not everyone looks as good as you do

If I understand correctly, you don't dress like this ALL this time - its just for occasional excursions, correct? When at home, do you wear anything fem? 

[JeffB]

2 hours ago, jeremy1986 said:

@JeffB- that's a great attitude and I applaud you for being so upfront and proud about it.

As you say, not everyone is in the same situation, and certainly not everyone looks as good as you do

If I understand correctly, you don't dress like this ALL this time - its just for occasional excursions, correct? When at home, do you wear anything fem? 

Other than experimenting with outfits to wear on jaunts for an hour or so on certain days when the mood strikes, nope.

[jeremy1986]

4 minutes ago, JeffB said:

Other than experimenting with outfits to wear on jaunts for an hour or so on certain days when the mood strikes, nope.

not at all - not even unmentionables?

[JeffB]

4 minutes ago, jeremy1986 said:

not at all - not even unmentionables?

Nope, not even that much.

[robbiehhw]

There are a whole lot of people on this spectrum and yours is a great example. Some people are also gender fluid, gender non-conforming and a-gender and those folks all have various and unique styles that they prefer (as we all do)

I think it is awesome that you choose to help society and get out there and be different. Society needs a lot more of that.

[Heelster]

I find I can easily get away with women's medium to low rise jeans in flare and boot cut with no issues as long as I don't have shiny bling on them - - nobody notices. I can pull off a calf high boot with a 1-1/2" (3.81cm) block heel with no problems (under flares) and nobody thinks twice. Even out here in the sticks!!

Locally - - I'm disinclined to push it.

[Cali]

I'm fashion fluid.

I openly wear 4 inch heels everyday, either with shorts or long pants. It's something I know I will do for the rest of my life because it's either that or pain. I mix men's and women's clothing on a day basis. I have many women's tops and outer wear that I mix into my daily (work) wear, including VS sweaters. There's so many more options in colors, textures, and styles- why limit myself. Always look alpha male, just in heels.

But my clothing's gender is male because it's mine, no matter where it started.