Anxiety venturing out

[hiddenheels]

I would like to "go big" once before the holidays. Would like to wear a mini-skirt with 4" knee-high almost stiletto boots, male stuff on top. I won't pretend to be a woman, don't want to, just want to wear what I want without pretense. 

Love the outfit I have in mind. However, although I've gone out in similar outfits in the past a few times, the boots were combat boots, or were hidden underneath jeans. So I think this one is a bit more daring. Right now, just thinking about it gives me serious anxiety. Sometimes I don't care, and just go for it, sometimes I'm completely up in my head, and can't get past my ingrained cultural role and what should be my "correct" presentation.

 

Does anyone have any tricks on overcoming this? Is it just practice-makes-perfect?

[mlroseplant]

As far as "tricks," there are none that I am aware of. You do eventually have to get out of the car, or step out of the house, as the case may be. The only piece of advice I have is that your "presentation" cannot be "correct" or "incorrect," but it certainly can be Wrong. The most important thing is to carry yourself in such a way as to be proud of who you are. The moment you look furtive, timid, or any such thing, people will pick up on that. Be friendly! Speak with a strong voice. Smile. I know it's tough with a mask, but smile anyway. People won't be able to dislike you if you act in this way and carry yourself in this way.

[pebblesf]

Not sure if I understand, have you ventured out in this outfit before?  The only advice I have is to move slowly in terms of outfit changes.  In other words, going from boots and jeans to a skirt with heels might be a big jump, more than you should expect to be able to handle with all the confidence that mlroseplant mentions.  

Maybe I have misunderstood your post, I would encourage you to post some pictures here before going out also, perhaps we can supply some support to bolster your confidence, as well as some constructive advice to help dial in your outfit....

[Pierre1961]

It’s more than a big jump! A totally different world.Which I don’t personally wish to get in. 

Look at Mark Bryan. Male clothes over the waist,female under. Amazing.Not my personal taste but amazing and have to congratulate. 

[hiddenheels]

Before I say anything else, I realize now I missed out an important point in my original post. The "combat" boots (I think that's the category they fit into) I'm talking about have a 4" heel, sorta like this:

 

 

Very much appreciate the sincere comments! It's been a tough few days, as I planned my outing outfit exactly, and noticed that the anxiety was very severe. Was planning on going out today, but after reading your responses, I realized that I might be pushing things a bit too much. So at the end, I swapped out my tall boots with the above combat boots, which I've worn outside with a skirt before. Similar to the last time, I sat around in the car for a long while, before I was able to stop thinking and get out of the car. Once outside, I had no issues with confidence, went to the food court, ate, did some shopping, went to another mall, did some more shopping. I might need a bit more time to adjust to heels/hose/skirt. Just wearing a 5" stiletto heel boot under my dress-pants is fine, did that multiple times without problems. Also did skirts without heels multiple times without problems.

 

Much appreciate the help. I think what I had in mind was a bit too much, and need some more "practice".

In the store, I was a bit self-conscious, mainly about the heels. The skirt I forget I'm wearing it. Overall the trip went well, no one said anything, although I know I got some looks. I will try to get a picture, but I couldn't find a decent mirror in the malls.

[pebblesf]

What a great outing for sure buddy....Seems like once you develop the courage/energy/confidence to get out of the car, there is no stopping you!  Can't wait to see some pictures...

Edited December 16, 2020 by pebblesf
grammar

[RonC]

The "combat boot", if they truly look like the ones in the photo, are quite obviously high heeled, feminine styled footwear.  To me, a knee high boot with a "near stiletto" heel doesn't seem to be much of a difference from these.  If I had the nerve to walk about in a skirt and the combat style boots, I wouldn't think much about the thinner heel knee high boot.  I think you've already reached the point where that shouldn't be that big of a step, as you've already pushed the limit as to what you feel you can wear.  That said, I still do understand the difficulty in doing what you are doing, and applaud you for how far you've come!

[hiddenheels]

6 hours ago, RonC said:

The "combat boot", if they truly look like the ones in the photo, are quite obviously high heeled, feminine styled footwear.  To me, a knee high boot with a "near stiletto" heel doesn't seem to be much of a difference from these.  If I had the nerve to walk about in a skirt and the combat style boots, I wouldn't think much about the thinner heel knee high boot.  I think you've already reached the point where that shouldn't be that big of a step, as you've already pushed the limit as to what you feel you can wear.  That said, I still do understand the difficulty in doing what you are doing, and applaud you for how far you've come!

Not sure why, but to me the two are different, and I'll practice a bit more before doing the knee high boot. Looking back, it was quite fun.  

Maybe I should drink a bunch of water before heading out in the car, maybe that'll give me another urgent reason to get out of the car when I get to my destination.

[Pierre1961]

Men’s rooms are not always a confortable place to go.Depends on who is also there 

[hiddenheels]

Decided to try to wear a pair of black pointy toed 5" stiletto ankle boots, sort of like the below image, but without the platforms (but including the red bottom - they look amazing, bought from Amazon, some Chinese brand). Was wearing my work getup, dress pants, etc. Wanted to gauge my anxiety. This time I had none. Parked, got out of the car, walked in the mall, bought some stuff, went to the other side of the mall to a coffee shop, bought some drinks, sat in the food court and worked, then went back to the car. Then I had to do some stuff I couldn't wear heels for. Some hours later, same getup, browsed around a thrift store. No anxiety.

I can walk comfortably in them, although need more practice to keep going for long. But felt fine, no one said anything. 2" of the heels showed when standing.

So no anxiety. OK... Really want to figure this out, and get rid of it... Thanks for listening.

 

 

EDIT: Removed the boots I originally posted, to be replaced by the actual boots I wore:

Edited December 18, 2020 by hiddenheels

[Jkrenzer]

Good for you. Not a fan of the platform you pictured. Why you just don't show what you were wearing baffles me, especially on this sight. The boots imaged are clownish, love to see what you actually wore.

Edited December 18, 2020 by Jkrenzer
Update

[hiddenheels]

2 hours ago, Jkrenzer said:

Good for you. Not a fan of the platform you pictured. Why you just don't show what you were wearing baffles me, especially on this sight. The boots imaged are clownish, love to see what you actually wore.

Have had my wife accidentally come across some of my posts on the internet, discussing heel wearing, and she freaked out. So security is high... Unfortunately. I really wish I could share more.

 

These are the boots. Tried to find it on Amazon, but it's no longer for sale.

[Tech]

1 massive life lesson I learned. "The only person who gives a crap about what you are wearing when you are not at work is you!"

Some guys get it right and look great, most get it wrong and look dreadful, and people will notice, laugh and move on with their lives, and still not care.

If you're keeping this a secret from your wife, you need to change that, and fast! Otherwise you going to end up a single guy, over some poxy footwear.

Seen guys make the wrong choice soooo many times, its sad. But have also seen guys make the right choice, and work things out.

But dont make it "A thing". If you make it "A thing" and "I have something to tell you" then your making footwear into a huge problem that it isnt.

Most womens biggest fear seems to be "First the heels, then the skirt, then something else, then the sex change...

[mlroseplant]

6 hours ago, Tech said:

But dont make it "A thing". If you make it "A thing" and "I have something to tell you" then your making footwear into a huge problem that it isnt.

Most womens biggest fear seems to be "First the heels, then the skirt, then something else, then the sex change...

My wife threatens to send me to Thailand, where they can do these sorts of things much cheaper, on a regular basis. I am quite sure that she's at least 80% joking.

[pebblesf]

On 12/16/2020 at 8:12 PM, hiddenheels said:

Not sure why, but to me the two are different, and I'll practice a bit more before doing the knee high boot. Looking back, it was quite fun.  

Maybe I should drink a bunch of water before heading out in the car, maybe that'll give me another urgent reason to get out of the car when I get to my destination.

This plan would surely work for me!

7 hours ago, hiddenheels said:

Have had my wife accidentally come across some of my posts on the internet, discussing heel wearing, and she freaked out. So security is high... Unfortunately. I really wish I could share more.

 

These are the boots. Tried to find it on Amazon, but it's no longer for sale.

I hear ya buddy....  Your relationship comes first, so don't post anything that will cause trouble for you...

7 hours ago, Tech said:

1 massive life lesson I learned. "The only person who gives a crap about what you are wearing when you are not at work is you!"

Some guys get it right and look great, most get it wrong and look dreadful, and people will notice, laugh and move on with their lives, and still not care.

If you're keeping this a secret from your wife, you need to change that, and fast! Otherwise you going to end up a single guy, over some poxy footwear.

Seen guys make the wrong choice soooo many times, its sad. But have also seen guys make the right choice, and work things out.

But dont make it "A thing". If you make it "A thing" and "I have something to tell you" then your making footwear into a huge problem that it isnt.

Most womens biggest fear seems to be "First the heels, then the skirt, then something else, then the sex change...

Sounds right to me....

1 hour ago, mlroseplant said:

My wife threatens to send me to Thailand, where they can do these sorts of things much cheaper, on a regular basis. I am quite sure that she's at least 80% joking.

 

 

Geez, I got ridiculed for wearing my frye campus boots over my jeans while shoveling the driveway!  Surprised I was able to go out shopping like this....

[hiddenheels]

14 hours ago, Tech said:

1 massive life lesson I learned. "The only person who gives a crap about what you are wearing when you are not at work is you!"

Some guys get it right and look great, most get it wrong and look dreadful, and people will notice, laugh and move on with their lives, and still not care.

That's what I'm finding out. However, I really do try to make my outfits look coordinated and professional. I do some research, and then experiment until I get something I'm happy with. Might not be to everyone's tastes, but I think it's OK.

 

14 hours ago, Tech said:

If you're keeping this a secret from your wife, you need to change that, and fast! Otherwise you going to end up a single guy, over some poxy footwear.

Seen guys make the wrong choice soooo many times, its sad. But have also seen guys make the right choice, and work things out.

But dont make it "A thing". If you make it "A thing" and "I have something to tell you" then your making footwear into a huge problem that it isnt.

Most womens biggest fear seems to be "First the heels, then the skirt, then something else, then the sex change...

While I agree with you in theory, I do not in practice. We've had that chat, she knows about the shoes, seen them, but doesn't want to deal with them or see them again. We've discussed it to death years ago, then things blew up, and had to keep it out-of-sight-out-of-mind. Over the years the issue has resurfaced multiple times, and has always ended up blowing up in my face. This is not something that will happen with her, so there is no way to "work things out".

[Cali]

16 hours ago, hiddenheels said:

Have had my wife accidentally come across some of my posts on the internet, discussing heel wearing, and she freaked out. So security is high... Unfortunately. I really wish I could share more.

Maybe its time to change your username and passwords.

[Bubba136]

11 hours ago, mlroseplant said:

My wife threatens to send me to Thailand, where they can do these sorts of things much cheaper, on a regular basis. I am quite sure that she's at least 80% joking.

Keep checking the credit cards to see if she bought you ticket.

[hiddenheels]

5 hours ago, Cali said:

Maybe its time to change your username and passwords.

You don't need any usernames/passwords to read these posts, or to come across an image of your partner on the internet.

[mlroseplant]

15 hours ago, Cali said:

Maybe its time to change your username and passwords.

 

9 hours ago, hiddenheels said:

You don't need any usernames/passwords to read these posts, or to come across an image of your partner on the internet.

Not only that, the consequences of keeping secrets like that can be quite severe. My wife would get very upset if she didn't know the code to my phone or the password to my email. However, she never looks at these things, and I don't look at hers. But we could if we wanted. I would hand her my phone for inspection at any time, even if there is the potential that it might be temporarily embarrassing.

[pebblesf]

17 hours ago, hiddenheels said:

That's what I'm finding out. However, I really do try to make my outfits look coordinated and professional. I do some research, and then experiment until I get something I'm happy with. Might not be to everyone's tastes, but I think it's OK.

 

While I agree with you in theory, I do not in practice. We've had that chat, she knows about the shoes, seen them, but doesn't want to deal with them or see them again. We've discussed it to death years ago, then things blew up, and had to keep it out-of-sight-out-of-mind. Over the years the issue has resurfaced multiple times, and has always ended up blowing up in my face. This is not something that will happen with her, so there is no way to "work things out".

My situation is similar hiddenheels...  My better half knows about my boots, but it is rarely discussed....Only in the heat of an argument.  My biggest regret is not wearing boots the night I met him, then he would known and could have made a decision whether or not to talk to me....  While I accept most of the responsibility for our issues, I think he could be a little more "accepting".  I too feel that our issues will probably never be "worked out", but know that my love of boots will never go away and can not be denied.  So, I would say that tech's advice is spot on, it is best to be up front on the first date...

Sure, some guys can pull off heels better than others, I wouldn't attempt to wear a skirt or hose.  The important thing is how you feel about how you look in your favorite heels/outfits, that is what counts buddy...  Take care...D

[p1ng74]

On 12/17/2020 at 10:55 PM, Tech said:

If you're keeping this a secret from your wife, you need to change that, and fast! Otherwise you going to end up a single guy, over some poxy footwear.

Seen guys make the wrong choice soooo many times, its sad. But have also seen guys make the right choice, and work things out.

But dont make it "A thing". If you make it "A thing" and "I have something to tell you" then your making footwear into a huge problem that it isnt.

Most womens biggest fear seems to be "First the heels, then the skirt, then something else, then the sex change...

 

3 hours ago, mlroseplant said:

 

Not only that, the consequences of keeping secrets like that can be quite severe. My wife would get very upset if she didn't know the code to my phone or the password to my email. However, she never looks at these things, and I don't look at hers. But we could if we wanted. I would hand her my phone for inspection at any time, even if there is the potential that it might be temporarily embarrassing.

Yeah, the internet is a horrible place to keep a secret.  But it is a great place for exchange of obscure interests.  

It might be a fine line, but I think there is a significant distinction between the two.  I figure the more I make high heels another one of my obscure interests, the less it becomes a big deal that damages relationships.  I participate in numerous online forums of various topics, and they are so boring to my wife that she would never take the time to read it.  Heck, we have been married for 13 years and she still finds my own public, personal blog to be too boring too read.  When we want to know each other, we spend time with each other, not snoop on each other on the internet.  

Edited December 19, 2020 by p1ng74

[Tech]

On 12/17/2020 at 1:12 AM, hiddenheels said:

Maybe I should drink a bunch of water before heading out in the car, maybe that'll give me another urgent reason to get out of the car when I get to my destination.

Would you do this with any other footwear?

This is where your turning it into "a thing". Your making something ordinary, albeit unusual, into something weird. If this wa s apair of trainers, you wouldnt think twice about it.

On 12/18/2020 at 11:12 AM, mlroseplant said:

My wife threatens to send me to Thailand, where they can do these sorts of things much cheaper, on a regular basis. I am quite sure that she's at least 80% joking.

You be surprised how much truth is often buried in a joke to test a reaction! She might well be waiting for you to to "come clean" by bringing it up repeatedly.

On 12/18/2020 at 7:54 PM, hiddenheels said:

That's what I'm finding out. However, I really do try to make my outfits look coordinated and professional. I do some research, and then experiment until I get something I'm happy with. Might not be to everyone's tastes, but I think it's OK.

Show us... Share a pic from the neck down...

[LuvsStiletto]

I remember the first time that I went out wearing 4” stiletto heels, vs. the 4” chunky/block heels that I had been wearing out, up to that point. The only real “difference”, was that of which was in my own mind. I was wearing lengthy boot cut jeans, which covered much of the tall, thin heel, however, whenever I walked past a shop window, I could see that a portion of the stiletto heel was still very much visible. In other words, the jeans helped cover them to an extent, but the combination of movement, the high heel “clicking sound” on the pavement, and the obviously pointed toes, clearly gave it away, that I was wearing stilettos. Despite all of that, aside from a few individuals quickly glancing at my choice of footwear, then carrying on, with whatever they were doing, it was basically a non-event. I find most people truly don’t care what type of shoes a stranger is wearing. At least for me, once I got over the “hurdle” imposed in my own mind, the experience itself is definitely exhilarating, but also somewhat disappointing, in that, the reactions you expect from passers by, often don’t match the expectations you set before you head out. It’s a good thing, in a way, but it also “robs” you of some of the “attention” you may or not have been expecting. When you experience enough of these instances, you begin to realize that most of society is more concerned with what they have going on, at the moment, than with some random guy they’ve never met, who happens to be wearing heels. Go at your own pace, but realize it’s only footwear. To those of us, who love heels, it’s obviously more, but most people who may notice, simply have too much else going on in their routines, to afford it much more, than that passing “glance”. Good luck!

[pebblesf]

34 minutes ago, LuvsStiletto said:

I remember the first time that I went out wearing 4” stiletto heels, vs. the 4” chunky/block heels that I had been wearing out, up to that point. The only real “difference”, was that of which was in my own mind. I was wearing lengthy boot cut jeans, which covered much of the tall, thin heel, however, whenever I walked past a shop window, I could see that a portion of the stiletto heel was still very much visible. In other words, the jeans helped cover them to an extent, but the combination of movement, the high heel “clicking sound” on the pavement, and the obviously pointed toes, clearly gave it away, that I was wearing stilettos. Despite all of that, aside from a few individuals quickly glancing at my choice of footwear, then carrying on, with whatever they were doing, it was basically a non-event. I find most people truly don’t care what type of shoes a stranger is wearing. At least for me, once I got over the “hurdle” imposed in my own mind, the experience itself is definitely exhilarating, but also somewhat disappointing, in that, the reactions you expect from passers by, often don’t match the expectations you set before you head out. It’s a good thing, in a way, but it also “robs” you of some of the “attention” you may or not have been expecting. When you experience enough of these instances, you begin to realize that most of society is more concerned with what they have going on, at the moment, than with some random guy they’ve never met, who happens to be wearing heels. Go at your own pace, but realize it’s only footwear. To those of us, who love heels, it’s obviously more, but most people who may notice, simply have too much else going on in their routines, to afford it much more, than that passing “glance”. Good luck!

So true buddy...

[mlroseplant]

I do find that things have changed in the last 10 years. I don't get nearly the attention I did when I first started wearing heels in public, even though my heels today are far more daring than they were back then. Before 2015, phones were out when I walked by! I'm very surprised I have never found myself on the internet somewhere. Today, I might get a few glances, I might even get a few grimaces, but nobody bothers to whip their phone out anymore.

[Cali]

I stopped for some my (coffee) beans for a month. I get a special blend I make.  The woman putting the beans in the bag asked if I wanted them blend and before I could answer, the one taking the money answered, "no, he the one that does it himself."   

I said "I thought you might know me by my heels" to which the she said, "heels?" and the woman getting the beans said "yeah, he always has nice heels on, what do you have on today?"

But the bug-eyed stare I got at Costco just before was classic. The older guy shopping with his wife couldn't keep his eyes off my heels, mouth ajar.  

[RonC]

8 hours ago, mlroseplant said:

Today, I might get a few glances, I might even get a few grimaces, but nobody bothers to whip their phone out anymore.

Do you think that might be due to the fact that, being in a smaller community, pretty much everyone already knows you, or knows about you, so it's no big deal to them any more?

[p1ng74]

I’ve worn heels in all sorts of strange, crowded places in different cities and never noticed anyone finding it a novelty worth snapping a photo for.  I do think we live in a time now where such things just aren’t that jarring.  

[Cali]

Times change, in 2004 we where in New Orleans and my niece had a vivid red hair color.  People would stop us and want to take a picture. Now hair color is so common no one cares to take a picture