Why do I feel like it is wrong?

[Thighmax]

I need some help.  I am going to tell you my thought process and maybe some of you experienced people can give me some insight.  

Ever since I was a little boy I have been in love with high heeled boots, I even asked my mother to let me use her boots, but she never did let me.  After some time I started experimenting with dresses, skirts and leather and fell in love with all of it.  I have even bought a couple of pairs of high heeled shoes which at one point was inconceivable.  

When I see myself in the mirror I feel sexy and powerful and I really like the end product.  I don't intend on passing as a woman, just wearing all the clothing.  

Unfortunately, I have found that when I see other men wearing the clothes I use (there are quite a few pictures on Pinterest), the thought in my mind is that it really doesn't look good and that maybe I shouldn't be doing it.  

I don't know if it is part of accepting myself, but every so often all this makes me doubt myself and really question if I should keep going or just stop and don't use this type of clothing.  

I feel really good wearing them, I have given it a lot of thought to actually start wearing my clothing outside, but as you can understand, there is something really powerful (in my mind) stoping me from actually doing it.

I have gone to therapists and they have told me there is nothing wrong with all of it.  

As you can see I have contravening thoughts about my style, I would appreciate it very much if you can tell me it this experience is new or not and how to grow from it.

thanks

 

[Shyheels]

I can understand your conflict. Personally I do not care for the look of men wearing women's clothes.To me it just strikes too many wrong chords - I'm not being judgmental about it, it just doesn't appeal to me in the least. On the other hand I can also understand your inner positive feelings. I have a pair of stiletto boots I like to wear around my home office with my otherwise masculine jeans and jumper - a silly thing perhaps but I feel more creative, liberated and expressive when I wear them.   

I can only suggest that if you are that conflicted, you might want to hold off on any plan to start wearing your outfits in public at least until you can do so with confidence. Resolve the issues and then go forward, striding out the door, with confidence. That will be the key. You need to own the look. To go out there with these doubts besetting your mind could be a recipe for disaster.  

Until then, enjoy your outfits for what they bring to you, read fashion magazines for fresh ideas and inspiration and stop looking at Pinterest.

 

 

Edited May 7, 2018 by Shyheels

[Cali]

This is a hard topic.  Have you seen pictures of what you look like?

I wear many different types of women's clothing on a daily basis.  Some is because of issues from some major injuries, other clothing I find fit me better than the men's version, or simply there is not a male version (like sleeves turtlenecks). I like fitted over loose, enjoy having more style/color than the drab clothing colors for men.  A good 60 - 70% of what I wear started on the woman's side, but you wouldn't notice unless you looked at the labels.  I wear Victoria's Secret tops and sweaters and get compliments. I have men asking where I found items all the time.

The point is, I found my happy zone, I pick and chose what I like and don't care what others say. I'm man enough to be my own man, I don't subscribe to lemming mentality. But I'm lucky to live in a tolerant area.

[Thighmax]

Thanks for both of your comments.  First off, I have looked at myself in the mirror and I feel really good about the way I look.  I have also looked at myself through pictures and somehow it doesn't feel quite as right.  I do believe that I shouldn't look at anybody else on Pinterest, won't do it again.  

I have been trying to write my thoughts for about 5 minutes now and I don't know how to express what I'm feeling.  

I guess, I would like to know what all of you have gone through, in terms of what your feelings have been. in order to help me comprehend what goes through my mind.  

[jeremy1986]

I think everyone here will have different 'flavours' of what you are describing. Some focus only on heels, others will take it further to clothes, and others might even take it further to blend in easier. no one will be in the exact position as you. And yet many of feel we are doing the "wrong thing" by wearing heels, or other feminine garments. I do too often.... but it still feels "right". Most folks will explain that its society's rules, telling us its wrong to do so. and if that's the case, you will need to decide what's right for you, and how far you are willing to go - whats your comfort zone. As you will read here, people comfort zone changes over time too ... 

[Steve63130]

Shyheels is absolutely right in his advice not to go out unless you are totally confident in your presentation. If you have doubts, it will show in your behavior and people can sense that. Go read through JeffB's pages of his freestyling experience and you'll see what I mean. He's confident and presents himself well. People see that and admire him. That's the kind of reception you want to get, too.

Good luck in your journey. We all have doubts along the line, but with experience (and taking baby steps) you'll find your path and it will be the right one for you.

Steve

[nzfreestyler]

There's sound advice offered thus far. I think this is a journey that we each make on our own because its very much a confidence game.

It comes down to confidence to do what you feel like. Take it in baby steps if you need to - a bit at a time.

For my 10 cents worth I only get positive feedback (hardly ever ever negative feedback and this has been empowering)

I started with heels alone and hid them for a while, but I felt awkward doing so, and so wanted to be open more.

Evolving to skirts was the best thing ever - but it was far harder a transition than just wearing high heels under long pants.(for me anyway).

Take it in baby steps - go out in public wearing heels, gauge how you feel - if you want more and are ok with it then add a skirt/dress etc. In my opinion work up to it but make sure you are happy with your image/outfit all the time. Let your style evolve as your confidence grows. It might happen quickly - it may be a slower process.

In terms of wearing high heels a lot - again this is a journey. If you desire to wear heels a lot you're going to have to work up to it over some time. I wear heels outside all the time (even for work now) and in my opinion high heels are a way of life - not just a shoe. To wear high heels well in the real world you must be a regular wearer - not just a short stint - so again its a journey and a natural evolution. (male or female - there are those who are good in heels and those that aren't). Confidence will also come from your ability in your heels.

I don't think about what is right or wrong by society - what I do isn't hurting anyone - I don't get in trouble, don't cause trouble. I get heaps of compliments - almost never get grief. People understand I'm just a guy who dresses differently!

 

 

 

 

[MackyHeels]

Always think about what i want to wear rather what i need to wear for others or my job duties. If i wear what others expect or enjoy or are happy seeing me in but i hate it, makes me depressed. At times makes me  angry when seeing other female dressed in something i could of worn or wanted myself instead played it safe appealing to my critics.

Then when i boldly have that itch to wear or desire a new outfit that is daring i become anxious because i closely observe for any reactions towards my style. Let's not kid ourselves people do observe men wearing unique outfit that is feminine styled colour, cut, fit etc... Often leads to judgement and mockery or very least bemused and or disgust shown outwardly if i keep close eye on everyone. Once i convince myself my outfit appears fashionable, envied by many, and importantly fits me well showing my body shape, liking well fitted clothes, i can feel encouraged to wear it without thinking about it. 

 

[bambam]

This is exactly how I feel. I feel good, I look good, but there is an existential predisposition that disallows this sort of experimentation. Seeing things like this continues to anger me, but I fear it also reinforces the 'masculinity' cage that all of us fight against, sometimes daily. 

https://www.thatsbetsyv.com/men-wearing-heels/

I think to a certain extent it needs to be an effort of courage, regardless. Safe spaces don't work, bravery does.

[nzfreestyler]

I just don't think about it.

In 'general' nobody nowadays thinks about anything important. Elections, policies etc - nobody in general really knows the details - nobody pays enough attention - or has the attention span to listen or read the words.... a bit brutal perhaps.....

So why care - I don't think about it - I just put on a skirt and high heels and head out (or perhaps a dress and heels) but either way I selfishly enjoy what I am doing.

Don't over think it - 'again a generalisation'.....     nobody else is thinking much these days....

[K2inheels]

Thighmax, I commend you on exploring what makes you feel good in terms of clothing and shoes. I can relate. I have been going through a similar transition. For me I started wearing heels over three years ago and now wear them the majority of time in public. Just recently I have been going through the process of wearing women's clothing. Not wearing dresses yet like nzfreestyler does (and I do wish I was at that point in my journey). But I do sometimes wear, blouses, shirt dresses with skinny jeans, etc. 

What I did to help me create a look and outfits is hire a stylist who worked with me and went shopping with me when I was out looking for new clothes. There were many time that she would look at me when I picked something out and she would tell me, "It's too young", "Won't fit your body", etc. Plus she helped me with colors (color blind). So now days I do wear women's skinny jeans and such when I am not at work.

I hope you will continue to push the boundary of your style and become comfortable in what ever you wear. Don't let society's narrow mind set determine what you should wear. We are all unique. Be colorful, be bold, be YOU. And do it with pride and confidence.

 

[pebblesf]

Thighmax-

I too have been "intriqued" by women's high heel boots, ever since I was a little kid.  I have gone through many stages, denial, shame, sneaking around, cowboy boots, but am finally accepting the fact that wanting to wear great women's boots is perfectly "normal", even though society tries to force us to believe it is "wrong" or "strange".  I truly believe that most men are intrigued by heels as well, but they suffer similar symptoms that I plagued myself with for too many years.  Keep in mind that it takes a great deal of courage to go against societies silly "rules", so overcoming these "blockades" shows a great deal of courage and confidence! 

The key is liking how you look in boots/women's clothing.  And, it sounds like you do like what you see when you look in the mirror.  I am admittedly confused when you say you don't like what you see when you look at your pictures though.  I'm glad that you sought out some advice from a counselor, this is very important.  Just keep in mind that counselors are just human like us, and it sounds like you didn't get much relief from the advice.  Perhaps you should find a different counselor, or try a few more sessions with your counselor. 

Starting off slowly is great advice, just like everyone here has advised.  This is a frustratingly slow process, building confidence to wear what you like takes a great deal of time, "baby steps" is the best way to describe it...I'm glad you have posted this thread, please know you are not alone and you have found like many like minded folks here.  We can't all be wrong! 

I hope you will post some pictures here, we are all here to help out, encourage you, even offer some gentle advice. 

[Shyheels]

As a photographer I think I might be able to shed light on why you don’t care for your image in pictures, but like what you see in the mirror. It is very hard to get someone to act naturally and relax in front of a camera in almost any circumstance - and lord know I’ve tried, on many a subject. But people can look into a mirror fairly readily and easily. 

So when you’re looking at a photograph, and looking critically, you’re likely to pick up on the (often subtle) tension in your pose and demeanour and that in turn has an impact on your overall perception.

Just a thought. But my guess is you look much more natural in the mirror, in loads of subtle ways that would be hard to put a finger on, but are there nonetheless. 

[Thighmax]

thanks for all your comments, I see that there are different perspectives to every situation and that is exactly why I want to keep reading whatever you have to say.  

On further thoughts, most of what I have is fear of what might happen to me or my family, I guess I will never know until I try it.  

When I see myself in pictures, I feel like I look really good, I feel confident.  Unfortunately, when I see other men dressed like this, it feels like there is something wrong with the look.  Therefore, my conclusion comes to thinking that there is something wrong with the look I portray.

I know that this has to do with stereotypes, but I can't help it.  I guess it is all a matter of getting used to something different.

[Shyheels]

I think it is seeing something expected. It jars us. To that extent doesn’t it really matter if it looks good if it unsettles or jars us at the same time. When I first tried on my stiletto boots I looked at myself critically and curiously in the mirror. What I saw was difference.  Something unexpected and a little unsettling. I had never seen myself in stilettos before. One does not expect to see a man in stiletto boots and it is in our nature to be unsettled by things that surprise us or make us question or doubt.

The look seemed odd - but not bad. I recognised that. My legs are slender and fit and long and actually do suit stiletto heels. If I wear them enough, over time, I am sure I’ll become quite used to seeing them on me and accept them as a matter of course. The surprise factor will diminish and fade.

Edited May 9, 2018 by Shyheels

[Cali]

Most of what you have seen written here is from men that live in western societies where there isn't the "machismo" that you might be experiencing.  I know when I traveled to South America my daughter warned me not to wear my heels. I wore some heels, but only my 2.5 inch heels and I only used clear nail polish. 

When I went to Australia, I was able to wear my high heels, but I again only had clear nail polish.

 

[pebblesf]

4 hours ago, Thighmax said:

thanks for all your comments, I see that there are different perspectives to every situation and that is exactly why I want to keep reading whatever you have to say.  

On further thoughts, most of what I have is fear of what might happen to me or my family, I guess I will never know until I try it.  

When I see myself in pictures, I feel like I look really good, I feel confident.  Unfortunately, when I see other men dressed like this, it feels like there is something wrong with the look.  Therefore, my conclusion comes to thinking that there is something wrong with the look I portray.

I know that this has to do with stereotypes, but I can't help it.  I guess it is all a matter of getting used to something different.

OK, well maybe you are concerned about the impact on your family/wife/kids, and that is a good sign that you are a caring/unselfish guy.  Does your wife know about your love of boots and feminine attire?  If so, how does she feel about it? 

[Shyheels]

He hasn’t mentioned experiencing any “machismo” element, only inner conflicts about the look he presented based on comparisons he had seen with similarly styled men on Pinterest. That has nothing to do with living in Latin America or anywhere else. They are concerns that would be shared by adventurous dressers anywhere and everywhere. And nobody would want to embarrass their family and friends

When it comes to that, there is plenty of machismo to be found right across western societies, including, dare I say it, the United States. 

Edited May 9, 2018 by Shyheels

[MackyHeels]

13 hours ago, Thighmax said:

When I see myself in pictures, I feel like I look really good, I feel confident.  Unfortunately, when I see other men dressed like this, it feels like there is something wrong with the look.  Therefore, my conclusion comes to thinking that there is something wrong with the look I portray.

I know that this has to do with stereotypes, but I can't help it.  I guess it is all a matter of getting used to something different.

Your not alone in that feeling. In fact i don't care how i appear in photos because i hate to look at myself. Heard actresses Kim Bassinger could not bare to watch herself in films.  In many respects i don't care to collect photos taken of myself on the beach even when others offer to send them. Often i reply with i see myself everyday in the mirror why do i need a photo to remind myself how i look like.  Yet i try to feel comfortable in the way i appear often is a battle hating or loving the way i see myself. While others i notice wearing clothing imitating my style, i too get annoyed even critical of how they appear. Laughable because i wear the same type of clothes as them, yet find myself tolerable even proud of my appearance. Yet same time find others dressed similar odd or uncomfortable to observe. Do know i won't judge there style or body composition trying to be tolerant of everyone. 

[Pierre1961]

I totally agree. 

I thought America,i mean at least West coast,some places  on the East coast and big cities  could be more permissive for men in heels. It seems it's not so different from " old" Europe. 

The funny thing is you get less ( negative?) reactions in Northern Europe than in the countries in the South.

I think machismo is not so present there or people are less inclined to show their feelings 

Pierre 

[Thighmax]

Thanks to all for the responses and for making me understand that after all, you choose what you like and it shouldn't matter what other people think about it.  I will let you know how everything goes!!!

[HappyinHeels]

Thighmax,

I do not know your age but nevertheless feel your words. The members here cover a large part of the spectrum from just wearing the heels to wearing them with other mixed articles from both the mens and womens sections to those who basically present themselves entirely in womens style clothes. A wide part of the expression spectrum but all within the normal spectrum clinically and psychologically.  Think about this for a minute. Do women you see dressed in jeans, t-shirts, sneakers, and baseball caps afraid of what others may think of them? Are they concerned whether some may think they are not "normal"? Normal has a way of evolving over the years. While some may think negative reactions may have to do with more "machismo" in some areas I am old enough to remember this word was commonly linked to Latin America. Did you know the two largest LGBTQ parades in the world now take place in Brazil and Mexico? "Normal" changes because peoples' perceptions and understandings change. You have no less right culturally or statutorily to wear women's style shoes than women have to wear men's.  The fact that you wear them and indeed enjoy the feel and look women's clothing and shoes means it has been an integral part of you all these years. You don't need a therapist to tell you that. Over the years I have written often about the need to always pack the one thing most needed to propel determined and happy people. That ingredient is confidence. It is the fire which fuels dreams and ideas and brings them into the open. We would never know of the historic acts of Abraham Lincoln, Rosa Parks, John F. Kennedy, those who fought back against the USSR in 1968 or Ronald Reagan telling Gorbachev to "tear down this wall" if it were not for their extraordinary amount of confidence.  Confidence=courage to express yourself. The world is not out to get you. It is, in fact, utterly neutral. It does, however, show deference toward those who show the most confidence. Whether you wear heels or not in public may seem so small compared to the historic people I mentioned but it is not a small matter to you right now.  You do not live in the U.S. or the U.K and so may never get the chance to meet another member here. Indeed  most of us talk here but have never met. We share our experiences of what we do alone. The companion you seek is the confidence living within you. Your post has ignited a flame of interest among us and now we pass the torch back to you. You came to the right place for support and inspiration. Muchas gracias! HappyinHeels

[Thighmax]

I truly appreciate your message, and the time that you have taken to write it down.  As I have mentioned before, I have been into high heeled boots since I was about 4 years old.  I could say it is second nature to me now.  When I was a kid I used my mother's boots, when my feet stared growing I found that hosiery was what I needed to use the boots.  Needless to say, I fell in love with hosiery.  

I ventured into dresses about two years ago, and liked the way they felt.  Unfortunately, when I saw myself in pictures I felt that it didn't look as good as it felt.  I didn't give up, I started changing brands and styles and found things that I liked.  Now, when I see myself in pictures I actually like what I see.  

As you can imagine, I like the way I look but have seen pictures of other men and find that they look to feminine and I am afraid that this is the image I project.  I don't intend to pass as a woman, I only like the clothes.  I know that with the clothing comes the territory, I will have to walk differently, sit and act differently in order to look good, this may look a little more feminine.  

After taking more picture I have found that my image, even though it is more feminine, doesn't really project the picture I was thinking.  Now, it is all a matter of having the guts to go out, which I know that will happen but it might take a little time.

thanks to you all for reading my posts.  

[WedgesAreFun]

On 5/7/2018 at 7:32 PM, Thighmax said:

When I see myself in the mirror I feel sexy and powerful and I really like the end product.  I don't intend on passing as a woman, just wearing all the clothing.  

Unfortunately, I have found that when I see other men wearing the clothes I use (there are quite a few pictures on Pinterest), the thought in my mind is that it really doesn't look good and that maybe I shouldn't be doing it. 

I feel exactly the same way. To my own eyes and mind it does not look right when I see other men wearing such things, yet I practice the same closeted activity myself in the privacy of my own home.

I am a hypocrite in this regard.

On 5/7/2018 at 7:32 PM, Thighmax said:

I don't know if it is part of accepting myself, but every so often all this makes me doubt myself and really question if I should keep going or just stop and don't use this type of clothing.  

I feel really good wearing them, I have given it a lot of thought to actually start wearing my clothing outside, but as you can understand, there is something really powerful (in my mind) stoping me from actually doing it.

This is why I keep it to a being just a closeted activity, I do not wish to present myself to the outside world in a way wherein I will be judged harshly and destroy my social standing among my peers. If I presented myself in womens clothing to the outside world I don't believe my peers or family would be wrong for judging me harshly when upon seeing my own reflection in the mirror.

On 5/7/2018 at 7:32 PM, Thighmax said:

I have gone to therapists and they have told me there is nothing wrong with all of it. 

It is easier for them to virtue signal about a life they don't or will not live themselves.

Reality is that the world is a harsh place and I am a realist. Life as a man is brutal but we do what we must, so we press on. Hats off to those brave enough to go against the grain, living their life for themselves and their own enjoyment, they have my respect for living as they please but I do not encourage it nor do I have any illusions that the world will EVER truly accept it even if the laws make such discrimination's illegal.

As a man life is a real struggle for me, it is suffering in silence, complaining does nothing but make others lose respect. The joys of being a man are few for me, but I will try to do my best to live my life as best as I can as man and get what enjoyment I can from my closeted activities within the sanctity of my home.

 

[Cali]

3 hours ago, WedgesAreFun said:

I feel exactly the same way. To my own eyes and mind it does not look right when I see other men wearing such things, yet I practice the same closeted activity myself in the privacy of my own home.

I am a hypocrite in this regard.

This is why I keep it to a being just a closeted activity, I do not wish to present myself to the outside world in a way wherein I will be judged harshly and destroy my social standing among my peers. If I presented myself in womens clothing to the outside world I don't believe my peers or family would be wrong for judging me harshly when upon seeing my own reflection in the mirror.

It is easier for them to virtue signal about a life they don't or will not live themselves.

Reality is that the world is a harsh place and I am a realist. Life as a man is brutal but we do what we must, so we press on. Hats off to those brave enough to go against the grain, living their life for themselves and their own enjoyment, they have my respect for living as they please but I do not encourage it nor do I have any illusions that the world will EVER truly accept it even if the laws make such discrimination's illegal.

As a man life is a real struggle for me, it is suffering in silence, complaining does nothing but make others lose respect. The joys of being a man are few for me, but I will try to do my best to live my life as best as I can as man and get what enjoyment I can from my closeted activities within the sanctity of my home.

 

@WedgesAreFunyour comments sadden me. One's life shouldn't be a struggle and suffering.

I switched to women's shoes over a decade ago when I finally figure out why I was having so many severe ankle problem (cause: men's shoes). I started to wear women's shoes and went through the fears of doing this fulltime. I started wearing 4 inch heels to heal a severe calf injury and found they helped another condition. So I have been wearing high heels since.

I have found a way to live as a man, but with softer clothes, more colorful clothes.  Don't limit your enjoyment.

[WedgesAreFun]

1 hour ago, Cali said:

@WedgesAreFunyour comments sadden me. One's life shouldn't be a struggle and suffering.

This is life sadly, I have come to terms with it and just try to do the best I can. Maybe the next one will be more fun and more body-appropriate for such simple joys, who knows? For now I have decided to accept things as they are and make do as best I can with what I have been given.

1 hour ago, Cali said:

I have found a way to live as a man, but with softer clothes, more colorful clothes.  Don't limit your enjoyment.

Thanks, I wish I could enjoy softer clothes and express myself in such colorful ways but I have to weigh the costs and benefits. The way I see it the costs greatly outweigh the benefits. So I have decided to live my life in this way as it just isn't worth it.

Edited May 13, 2023 by WedgesAreFun

[ohnoberty]

Society's norms and acceptance! Clearly the world has eveloved in the last number of years, being more tolerant and accepting of individual's uniqueness. Sadly though it's a long way from giving people the reassurance that many/most need to venture out wearing whatever they like without the huge burden and concern about stigma, finger pointing and repercussions.

Not everyone finds a way to reach what they might feel is their goal, and so we keep part of our lives completely to themselves, sadly. On a brighter side though, having forums like this allows people to share their feelings, even if we make no further changes, it still helps in allowing us to live more easily with who we are.

 

[mickeyunc]

I understand 100%.  I think alot of men struggle with this topic.  i for 1 like to wear womens clothing, but i do so without looking like a female.  i like to wear outside of my home and when i go to a local mailbox to drop offmail, all be it in the evening.  also will stop on side of roads and get out and walk a bit, parking lots and parks.  guess what iam saying if me i would dress and look like a female and pull it off

[pebblesf]

1 hour ago, mickeyunc said:

I understand 100%.  I think alot of men struggle with this topic.  i for 1 like to wear womens clothing, but i do so without looking like a female.  i like to wear outside of my home and when i go to a local mailbox to drop offmail, all be it in the evening.  also will stop on side of roads and get out and walk a bit, parking lots and parks.  guess what iam saying if me i would dress and look like a female and pull it off

Well said brother!  I wear my boots, but as a guy.  Would like to wear more female gear, but don't have the bod to pull it off very well.  The look you describe is a very powerful and confident look indeed, which translates into masculinity!

[mlroseplant]

I can remember the first time I ever looked in the mirror (at approximately age 20, or 35 years ago) while wearing high heels, and thought to myself, "God, I look absolutely terrible, I'm never letting anybody see this." And it was true, I did look terrible.

It had nothing to do with the actual clothing or shoes, it had everything to do with the way I carried myself. I guess I've always known it, but for most of my life, I have looked terrible moving through the world--bad posture and a funny walk with bowed legs. I still catch myself doing this from time to time, I have to work at it constantly, and I'm never really satisfied. It's even worse now that I'm on livestream video every single week, I get to see what happens when I'm thinking about what's going on in the moment, and not how I'm carrying myself. "Wow.  .  . did I just walk down those steps like that?" (Involuntary shudder).