So very thoroughly confused!

[hiddenheels]

Alright, I'm completely confused. Can't make heads or tails of my thoughts. Haven't slept well for the past few days. For the past two decades I have worn heels exclusively at home, with very very infrequent outings, at night. In the last year I started wearing them out more, have bought a few boot-cut jeans to hide the heels, have become more comfortable with myself, and being outside in heels. The jeans cover most of it anyway, and thus far I have not received any comments. Have been to a few stores, and coffee shops, usually  quite self conscious, sometimes am able to relax and just enjoy things. Never been interested in more than heels.

Then on Saturday I find some black pantyhose in my stash of jeans, don't remember how it got there, but thought I would try it on with one of my black knee-boots. Ended up thinking that a skirt would complete the look. So Sunday I stop by a second-hand store, quickly grab two mini-skirts that look good and will probably fit. Monday I had a few hours at home, and the first thing I do is try things on, black pantyhose, 4-5" stiletto black knee-boots, and a grey mini-skirt that went down to mid-thy. Now, this is probably the first time I try on skirts, and never considered it, never was curious about it, but the look and feeling was amazing. I have no ideas how to match the top with the bottom, meaning, what shirt or sweater I need to complete the look because I don't want to "pass", I have stubble and am not going to put on makeup or wear a wig (no disrespect, but that's not my thing). But I don't know how to complete the outfit, well, because I have never thought what I would wear if I wore a skirt. After some brief trial-and-error I figure the jacket completes the look quite well, and thus the shirt is largely irrelevant. And look in the mirror.

What I saw confused the heck out of me. It was comfortable, I felt comfortable, but at the same time super-weird. That was the most unusual look I have seen on me, and I couldn't place it at all. WTF was I doing?

Given my pattern with heeling outside, never obviously showing the heels, the logical thing at this point for me would have been to enjoy the experience at home, in private. But no. I had this indescribable urge to be outside. It was overwhelming. It was dark outside, late evening. I got into the car, and went to a place that I infrequent for heeling, a small park in a residential neighbourhood. Park, and without any major self-talk, get out of the car and start walking. The entire walk took about 15 minutes total, beside some houses and roads. Some cars passed, I met no other person walking. Parts of the trip was under heavy lighting, beside some condos. I didn't meet anyone, nor talk to anyone. Skirt was mostly visible. Boots completely uncovered. I felt "normal", didn't care that my legs showed.

I frequently get the fight-or-flight response, trying to stop my heart from jumping out. After a while that goes away, and I become calmer. If I'm able to relax more, I end up usually happy/thrilled with the experience. This time I was rather calm the entire time, no panicking, no low or high emotions. Was focusing on just walking. Would say it was more like a state of "what is just happening, I can't comprehend this"?

In short. The experience was fantastic. I loved it. But my mind hasn't stopped reeling since that night. I can barely sleep. I have all sorts of mixed up feelings. Why did I do that? I'm not ashamed, but it was completely out of character. What the heck do I want with this. What was I thinking? Where is this going? Is this something new that I will eventually want to explain to my wife? Why can't I be "normal" (according to society)?

 

[I'm not comfortable sharing images, this is as good as it'll get]

Edited February 21, 2020 by hiddenheels

[Cali]

The sensations you got from the pantyhose over powered your trepidations about being seen. Aka Forbidden Fruit Syndrome.  Since you have to fine time to wear your heels, the addition of pantyhose just overwhelmed you.

Yes, skirts are very comfortable. Wore a faux leather one for 16 hours on Halloween and completely enjoyed it. It was very comfortable although a little different driving because it was a tight skirt.  As to what top to wear with it...the coat looks good with the skirt, keeping it monochrome, but your shirt/top distracts from the overall image, IMHO. As to how to process this, that's really a personal thing that everybody processes this differently.  

Edited February 21, 2020 by Cali

[pebblesf]

I would say that your varied emotions are completely normal.  Wearing a skirt, hose and completely exposed boots is a big step from wearing your boots covered with jeans.  You are having an internal struggle with the societal pressures we all have to deal with.  You look great as a guy in a skirt/boots, you should be able to enjoy the benefits of taking care of your body so you can look so good in this outfit.  You will eventually find out that many women think you look great as well, don't let you mind play these horrible games with you....Read about CAT's adventures, or W6ish also.  

For now, I would choose your outings very carefully....A negative experience usually results in a large emotional set back...  Congratulations to you, be proud of being to brave....I am surely envious..

 

 

 

[maninboots]

Not sure where you found this sudden urge from but stick with it, you look fantastic, I’ve never worn a skirt in public but I do like to show my knee high boots off over my skinny jeans which I suppose is half way there, after seeing your picture i may have to do a bit more experimenting, well done and thanks for some inspiration 

[hiddenheels]

6 hours ago, pebblesf said:

I would say that your varied emotions are completely normal.  Wearing a skirt, hose and completely exposed boots is a big step from wearing your boots covered with jeans.  You are having an internal struggle with the societal pressures we all have to deal with.  You look great as a guy in a skirt/boots, you should be able to enjoy the benefits of taking care of your body so you can look so good in this outfit.  You will eventually find out that many women think you look great as well, don't let you mind play these horrible games with you....Read about CAT's adventures, or W6ish also.  

For now, I would choose your outings very carefully....A negative experience usually results in a large emotional set back...  Congratulations to you, be proud of being to brave....I am surely envious..

Thanks for the words of encouragement. I was hoping I was making good progress with this internal struggle. I was finding my way and getting used to wearing heels with jeans, and venturing out whenever possible. I was falling into a routine, with cloths and feelings, and all that. Now this threw a monkey-wrench into the whole thing... Now I'm feeling like I'm starting from scratch with everything.

One thing for sure, it certainly makes the jeans look tame in comparison.

 

34 minutes ago, maninboots said:

Not sure where you found this sudden urge from but stick with it, you look fantastic, I’ve never worn a skirt in public but I do like to show my knee high boots off over my skinny jeans which I suppose is half way there, after seeing your picture i may have to do a bit more experimenting, well done and thanks for some inspiration 

Thanks to you too for the encouragement. I have now calmed down a bit, and am starting to process what the heck is going on. Will have to get some more skirts to experiment with, as this is completely new territory for me and I have no real clue what I'm doing. Fortunately these things are ~$5 at second hand stores, which make it perfect for experimenting.

 

12 hours ago, Cali said:

The sensations you got from the pantyhose over powered your trepidations about being seen. Aka Forbidden Fruit Syndrome.  Since you have to fine time to wear your heels, the addition of pantyhose just overwhelmed you.

Yes, skirts are very comfortable. Wore a faux leather one for 16 hours on Halloween and completely enjoyed it. It was very comfortable although a little different driving because it was a tight skirt.  As to what top to wear with it...the coat looks good with the skirt, keeping it monochrome, but your shirt/top distracts from the overall image, IMHO. As to how to process this, that's really a personal thing that everybody processes this differently.  

For top, what would you suggest? I am honestly clueless with how to proceed. I tried different colours but nothing really worked in my eyes. Any advice would be appreciated.

 

Thanks!

Edited February 21, 2020 by hiddenheels

[RonC]

You looked great in that outfit.  You have progressed fantastically in satisfying your desire to wear heels.  I wish I had the nerve to try a skirt and heels in public, even if no one really saw me.  I did don a skirt, hose and heels and visit drive-thrus a few times, but never had the nerve to get out of the car.  Go at your own pace to whatever is next!

[hiddenheels]

Haven't ventured outside in any outfit since that time, but did manage to buy some more skirts at a second-hand store, specifically was looking for denim skirt, as I really like that look. I've experimented around at home, and have found that the look is simply awesome. I love it. I feel comfortable in them, both physically, and increasingly emotionally. That first experience was completely overwhelming, and I'm still reading, researching, etc, on how this works, what styles look good, etc.

Any style tips would be super welcome.

[bailey]

Thrift stores are a great place to find those hidden gems for next to nothing. Denim skirts are a great option. Just like denim jeans, they are casual, and tend to work with a number of colors, patterns and textures. Once paired with hosiery they will go with many styles of heels, whether it be wedges, stiletto, or block heel designs. Not to mention boots of all styles. This is an example of one my denim skirts.

Edited February 24, 2020 by bailey

[RonC]

I always liked the look of a denim skirt with a pair of dressy heels.  The kind of incongruous look I've always enjoyed - wearing heels with casual styled clothing.

[chesterx]

On 2/23/2020 at 8:25 PM, bailey said:

 

I soooo want to try that look...

[mlroseplant]

I don't know how I feel about skirts and such, these 8 years later, now that I wear heels all the time without too much self consciousness. I think I could probably look good in a skirt, maybe rather better than some others, but I just don't really have any desire to, and creating one sort of artificially by going out and buying a skirt at a thrift store just so's I could try it out seems to me to be .  .  . rather foolish. It would create way more complication in my life than there is already. I get enough of a thrill with wearing shorter shorts, and for some reason this is more acceptable to the wife than wearing any kind of a skirt would ever be.

[SkirtDude]

I love showing off my booties, and an A-line of sensible length is great to do so. This is my 'tartan' 21 inch. I think your skirt looks great as well, OP! 

Edited February 25, 2020 by SkirtDude

[hiddenheels]

On 2/23/2020 at 6:25 PM, bailey said:

Thrift stores are a great place to find those hidden gems for next to nothing. Denim skirts are a great option. Just like denim jeans, they are casual, and tend to work with a number of colors, patterns and textures. Once paired with hosiery they will go with many styles of heels, whether it be wedges, stiletto, or block heel designs. Not to mention boots of all styles. This is an example of one my denim skirts.

This looks great, never thought about wedges, but the look works!

 

7 hours ago, mlroseplant said:

I don't know how I feel about skirts and such, these 8 years later, now that I wear heels all the time without too much self consciousness. I think I could probably look good in a skirt, maybe rather better than some others, but I just don't really have any desire to, and creating one sort of artificially by going out and buying a skirt at a thrift store just so's I could try it out seems to me to be .  .  . rather foolish. It would create way more complication in my life than there is already. I get enough of a thrill with wearing shorter shorts, and for some reason this is more acceptable to the wife than wearing any kind of a skirt would ever be.

Hey, I completely know where you're coming from. I don't know if/how I could broach this subject with my wife, I really don't want any conflict especially over this. But until a week or two ago, I never thought about skirts either, did nothing for me, until I tried them... One step at a time.

 

1 hour ago, SkirtDude said:

I love showing off my booties, and an A-line of sensible length is great to do so. This is my 'tartan' 21 inch. I think your skirt looks great as well, OP! 

That is awesome, love that plaid skirt look! I did order one of these a few days ago, will take forever to get here though, can't wait. Having said that, went to another second-hand store yesterday and did manage to snag a skirt similar to yours, but in blue (instead of black). It's small, but for $5 I couldn't resist. Will have to move (re-sew) some of the buttons after which it'll fit great. The one I bought it was too long, goes down to my knees, so I will also need to take a pair of scissors to it. In my mind, it'll look great, just need a few hours to experiment with it, which will not happen in the near future.

 

------------

Sunday night managed to go out again! It was already dark outside, in a residential neighbourhood, a few cars passed by, but nothing else happened. Similar outfit to the above, but a "safer" chunky heel 4" ankle boots with a new-to-me denim skirt. Parked, and without another thought managed to get out of the car, adjust myself and start walking. The walk was about 20 minutes, and felt completely natural, wasn't nervous, and was able to just enjoy the quiet and the walk. Interestingly enough, with the heels and skirt "out in your face" (as opposed to hiding it under my jeans), for whatever reason, I actually felt more comfortable. "It's there, can't hide it, so might as well enjoy it." Not sure I would have the courage yet to go somewhere with a lot of people though... At least a few more trips out at night are most likely required.

[p1ng74]

I find skirts to be very comfortable pieces of clothing.  I think men who are afraid to try them might be missing out, though men wearing skirts seems to be less weird than men wearing heels, given that I have seen more of the former than the latter in public.  Not only are skirts comfortable, but they are stylistically more versatile.  Personally, I think of shorts as being extremely casual, down there with sweat pants, and there are many fine establishments that would agree with me and not let you in wearing shorts.  Kilts and skirts, on the other hand, have a variety of established associations that include formal wear.  I have a personal goal this summer to wear kilts in lieu of shorts when it gets too hot and uncomfortable for pants.  We'll see how that goes.  

And all that is not even related to footwear.  But on top of being cooler for hot weather, skirts offer more opportunity to show off your footwear, so there is additional interest for heel wearers as well.  

I might be wrong on this, but I try not to overthink the process of pairing a skirt with the rest of the outfit, and treat it like any other bottom, whether it be pants or shorts.  Match the color, style, etc. - I don't think there is anything that inherently "doesn't work" with skirts, just like how it doesn't seem like there is anything that inherently doesn't work with jeans.  I try not to think too much of it as a skirt, but a bottom to be paired, and roll with it.  

 

 

Edited February 25, 2020 by p1ng74

[Peter1]

Well done @hiddenheels for your last outings, you look so great in this outfit!

it’s impressive how fast you make progress in your heels journey! I completely understand your thought, but as your are becoming confident by wearing your heels in public with jeans, it seems normal that you want to expand your comfort zone.

There is nothing wrong wearing a skirt with some nice boots, life is too short as some said !
Thanks fo sharing your experience, that will help a lot of us becoming bolder!

 

 

Edited February 25, 2020 by Peter1

[hiddenheels]

3 hours ago, p1ng74 said:

I might be wrong on this, but I try not to overthink the process of pairing a skirt with the rest of the outfit, and treat it like any other bottom, whether it be pants or shorts.  Match the color, style, etc. - I don't think there is anything that inherently "doesn't work" with skirts, just like how it doesn't seem like there is anything that inherently doesn't work with jeans.  I try not to think too much of it as a skirt, but a bottom to be paired, and roll with it. 

You are assuming I have a sense of style... I don't think I do, at least not without extensive trial-and-error, after which I think I can put together an outfit that I think looks good. But I've done this "I think it looks good" with traditional male cloths, and my wife completely disagrees with me. So it's hard. And I don't want to shave my legs, so am not sure what to do there either: go unshaved, or try to hide it, but then how?

Tips would be appreciated.

3 hours ago, Peter1 said:

Well done @hiddenheels for your last outings, you look so great in this outfit!

it’s impressive how fast you make progress in your heels journey! I completely understand your thought, but as your are becoming confident by wearing your heels in public with jeans, it seems normal that you want to expand your comfort zone.

There is nothing wrong wearing a skirt with some nice boots, life is too short as some said !
Thanks fo sharing your experience, that will help a lot of us becoming bolder!

Thank you for the encouragement, no one is more surprised about this than I am. 20 years of hiding and feelings of disgrace... and now as I try to accept and embrace it, instead of pushing it away, in 6 months I'm going out in a skirt with the heels fully visible (albeit at night). Very exciting!

[p1ng74]

1 hour ago, hiddenheels said:

You are assuming I have a sense of style... I don't think I do, at least not without extensive trial-and-error, after which I think I can put together an outfit that I think looks good. But I've done this "I think it looks good" with traditional male cloths, and my wife completely disagrees with me. So it's hard. And I don't want to shave my legs, so am not sure what to do there either: go unshaved, or try to hide it, but then how?

Tips would be appreciated.

Aesthetics can be subjective, and finding what “looks good” and being able to justify it with others is something that takes a bit of time and effort, at least for me.  This extends beyond just taking time to put together an outfit - there is much to be learned looking at what designers and designing, what people are wearing, and deciding why it looks good or doesn’t.  And then there is the personal expression component, taking time to put together what it is you really are trying to say with your clothes.  

As for shaving, I realize a lot of people here so it, but I also have to ask:  Has anyone ever given men grief for not shaving their legs while wearing shorts?  Why should a skirt be any different?  The same amount of legs are being shown...

[SkirtDude]

13 hours ago, hiddenheels said:

This looks great, never thought about wedges, but the look works!

 

Hey, I completely know where you're coming from. I don't know if/how I could broach this subject with my wife, I really don't want any conflict especially over this. But until a week or two ago, I never thought about skirts either, did nothing for me, until I tried them... One step at a time.

 

That is awesome, love that plaid skirt look! I did order one of these a few days ago, will take forever to get here though, can't wait. Having said that, went to another second-hand store yesterday and did manage to snag a skirt similar to yours, but in blue (instead of black). It's small, but for $5 I couldn't resist. Will have to move (re-sew) some of the buttons after which it'll fit great. The one I bought it was too long, goes down to my knees, so I will also need to take a pair of scissors to it. In my mind, it'll look great, just need a few hours to experiment with it, which will not happen in the near future.

 

------------

Sunday night managed to go out again! It was already dark outside, in a residential neighbourhood, a few cars passed by, but nothing else happened. Similar outfit to the above, but a "safer" chunky heel 4" ankle boots with a new-to-me denim skirt. Parked, and without another thought managed to get out of the car, adjust myself and start walking. The walk was about 20 minutes, and felt completely natural, wasn't nervous, and was able to just enjoy the quiet and the walk. Interestingly enough, with the heels and skirt "out in your face" (as opposed to hiding it under my jeans), for whatever reason, I actually felt more comfortable. "It's there, can't hide it, so might as well enjoy it." Not sure I would have the courage yet to go somewhere with a lot of people though... At least a few more trips out at night are most likely required.

Glad you like it! Don't alter the knee length skirt, just go and wear it! It may even pass as a "kilt" to some  I found that going out at night, although comforting due to the lack of people, also made me feel I was creeping about a bit, so I decided to just bite the bullet, go to a grocery store and buy something, like some milk (I had ran out). You'll find few people will even react to your attire, and if any do, it's compliments! It takes balls for a guy to go outside the usual jeans or shorts look, there's a growing "genderfluid" trend of dress, with instagrammers like @joshohhgosh who frequently are skirted, or EJ Johnson. I wear regular guys shirts / tops, but a denim skirt instead of denim shorts. You have to show us your denim skirt look 

Edited February 26, 2020 by SkirtDude

[balletboot]

I went through this same thing I didnt post much on here about my confusion I just posted about my outing and how they went. 

I started like you (and many others I'm sure) years ago going out at night hoping no one would be around. And then one day I was driving somewhere in heels and I stopped at a store to get something and I kinda forgot I was wearing my heels. Withing the first 30 feet of walking into the store a younger woman complimented me on my heels. I was completely thrown off guard and I looked down and realized I was still wearing them. Told her thank you and quickly finished my shopping and left.

Later to realize how much it doesnt matter that I was wearing heels. After that I started doing all my shopping in heels. Within a few months I was wearing skirt and pantyhose with mens shirts and jackets. To me they are way more fun than pants, more comfortable and alot of the times better looking!

The only part that has been a problem for me is my girlfriend hates all of it. Which I've been struggling to get across to her that they are just clothes and why cant I enjoy them. She thinking I must be gay because of it, but those of us here know that isnt the case..

 

Good luck to you and keep trying to get out and about! It makes everyday things more exciting and enjoyable! 

[hiddenheels]

20 hours ago, SkirtDude said:

Glad you like it! Don't alter the knee length skirt, just go and wear it! It may even pass as a "kilt" to some  I found that going out at night, although comforting due to the lack of people, also made me feel I was creeping about a bit, so I decided to just bite the bullet, go to a grocery store and buy something, like some milk (I had ran out). You'll find few people will even react to your attire, and if any do, it's compliments! It takes balls for a guy to go outside the usual jeans or shorts look, there's a growing "genderfluid" trend of dress, with instagrammers like @joshohhgosh who frequently are skirted, or EJ Johnson. I wear regular guys shirts / tops, but a denim skirt instead of denim shorts. You have to show us your denim skirt look 

Thanks! I haven't had a chance to experiment at all with it, but I am really leaning towards shortening it, it's just too long for my taste. I will try to post a before/after picture.

Regarding going out at night, I have the same thoughts. Going out at night is safe, in that noone will probably see you, but at the same time the fact that (at the moment) I'm only comfortable going out at night makes me feel bad, as in I'm doing something bad. It'll take me a bit of time to get used to this idea, and find something I'm comfortable in, before I even think of venturing to a store or something. I'm glad to hear I'm not the only one going through these thoughts.

 

9 hours ago, balletboot said:

I went through this same thing I didnt post much on here about my confusion I just posted about my outing and how they went. 

I started like you (and many others I'm sure) years ago going out at night hoping no one would be around. And then one day I was driving somewhere in heels and I stopped at a store to get something and I kinda forgot I was wearing my heels. Withing the first 30 feet of walking into the store a younger woman complimented me on my heels. I was completely thrown off guard and I looked down and realized I was still wearing them. Told her thank you and quickly finished my shopping and left.

Later to realize how much it doesnt matter that I was wearing heels. After that I started doing all my shopping in heels. Within a few months I was wearing skirt and pantyhose with mens shirts and jackets. To me they are way more fun than pants, more comfortable and alot of the times better looking!

The only part that has been a problem for me is my girlfriend hates all of it. Which I've been struggling to get across to her that they are just clothes and why cant I enjoy them. She thinking I must be gay because of it, but those of us here know that isnt the case..

 

Good luck to you and keep trying to get out and about! It makes everyday things more exciting and enjoyable! 

Thank you for sharing that! Means a lot.

I have so far been really careful about where/when I wear my things, but sometimes I also tend to forget what I'm wearing, and have almost had a few such incidents like you.

Would you mind sharing some details about your confusion, or internal struggle? The last few months have been really hard sometimes due to this struggle. Ups and downs. I'm OK right now, but there are times when it's a lot of anger. Thanks!

[jeremy1986]

Coming in late to this thread, but can only say that I totally feel your confusion.... while I am not at the same place as you, I share that same confusion, not to mention the pressure from my SO and within my own head, that its something "wrong" and I should be 'cured' and be 'normal' 

Wishing you well, @hiddenheels mate! Stay healthy and safe - and keep us posted! 

[hiddenheels]

I'm expending my energy by shopping. Went to a second-hand store a few days ago and bought another two skirts, one which fits really nicely as is, and another which I'm taking some scissors to, I have something planned for that. :)

 

Today, wasn't planning on buying anything, but happened to have 30 minutes to kill at a mall while I waited for someone. Walked around, and found a store that looked like it was going bankrupt (it wasn't), but they had a massive section of super-cheap stuff. I ended up buying three brand new skirts, a denim mini-skirt that looks like it's torn for like 5$, a white mini-skirt and a beige one for 2-for-5$. All fit perfectly. Also found a pair of heels, they look sort of like running shoes, but have a stiletto heel and the front is pointy. I think it looks amazing. I have no idea how, but ended up paying ~22$ for the entire collection! All brand new stuff, lots of variety. Will have to go back when I have a bit more time. Will try to post pictures when possible.

[jeremy1986]

On 2/28/2020 at 5:26 AM, hiddenheels said:

I'm expending my energy by shopping. Went to a second-hand store a few days ago and bought another two skirts, one which fits really nicely as is, and another which I'm taking some scissors to, I have something planned for that.

 

Today, wasn't planning on buying anything, but happened to have 30 minutes to kill at a mall while I waited for someone. Walked around, and found a store that looked like it was going bankrupt (it wasn't), but they had a massive section of super-cheap stuff. I ended up buying three brand new skirts, a denim mini-skirt that looks like it's torn for like 5$, a white mini-skirt and a beige one for 2-for-5$. All fit perfectly. Also found a pair of heels, they look sort of like running shoes, but have a stiletto heel and the front is pointy. I think it looks amazing. I have no idea how, but ended up paying ~22$ for the entire collection! All brand new stuff, lots of variety. Will have to go back when I have a bit more time. Will try to post pictures when possible.

Sounds like the confusion is clearing up

Enjoy the new items!

Edited March 1, 2020 by jeremy1986

[SkirtDude]

On 2/28/2020 at 3:26 AM, hiddenheels said:

I'm expending my energy by shopping. Went to a second-hand store a few days ago and bought another two skirts, one which fits really nicely as is, and another which I'm taking some scissors to, I have something planned for that. :)

 

Today, wasn't planning on buying anything, but happened to have 30 minutes to kill at a mall while I waited for someone. Walked around, and found a store that looked like it was going bankrupt (it wasn't), but they had a massive section of super-cheap stuff. I ended up buying three brand new skirts, a denim mini-skirt that looks like it's torn for like 5$, a white mini-skirt and a beige one for 2-for-5$. All fit perfectly. Also found a pair of heels, they look sort of like running shoes, but have a stiletto heel and the front is pointy. I think it looks amazing. I have no idea how, but ended up paying ~22$ for the entire collection! All brand new stuff, lots of variety. Will have to go back when I have a bit more time. Will try to post pictures when possible.

It's so easily done! Whilst waiting for a new skirt to arrive (much longer pencil for work), I stumbled into a thrift shop, and ended up with a blouse and three skirts! 2 of which fit, so not bad. The blouse fits like a glove. Looking forward to seeing pics! Next skirt is a new skater skirt, a first for me amongst pencils and A-lines 

[hiddenheels]

10 hours ago, SkirtDude said:

It's so easily done! Whilst waiting for a new skirt to arrive (much longer pencil for work), I stumbled into a thrift shop, and ended up with a blouse and three skirts! 2 of which fit, so not bad. The blouse fits like a glove. Looking forward to seeing pics! Next skirt is a new skater skirt, a first for me amongst pencils and A-lines 

Haha, agreed that it "just happened"! For a price that low, I couldn't resist.

 

12 hours ago, jeremy1986 said:

Sounds like the confusion is clearing up

Enjoy the new items!

Thanks for pointing that out to me, it does seem like the confusion is clearing up, yes... How I could broach this to my wife, I have no idea. Even the heels cause a lot of fuss and stress, I can't even imagine the reactions if I keep pushing it with her. Sigh...

[jeremy1986]

On 3/2/2020 at 2:44 AM, hiddenheels said:

Thanks for pointing that out to me, it does seem like the confusion is clearing up, yes... How I could broach this to my wife, I have no idea. Even the heels cause a lot of fuss and stress, I can't even imagine the reactions if I keep pushing it with her. Sigh...

I hear ya, mate. I still don't know how I did it myself, with heels. if it means a lot to you, you will have no choice but to breech it with her and work it through. 

[hiddenheels]

Have been trying to wear one of the skirts out in daylight, but even when I had the chance, I didn't have the courage. Feelings of being a failure come back... Not just a failure to wear what I want, but thoughts of "why am I doing this to myself"... If life were a rollercoaster, at the moment I'm headed down...

[mlroseplant]

15 hours ago, hiddenheels said:

Have been trying to wear one of the skirts out in daylight, but even when I had the chance, I didn't have the courage. Feelings of being a failure come back... Not just a failure to wear what I want, but thoughts of "why am I doing this to myself"... If life were a rollercoaster, at the moment I'm headed down...

Eh, don't be too hard on yourself. It takes a lot of mental energy to present oneself in a different way. Sometimes that mental energy just isn't there. It's not a failure, it's simply another day in the life.

[RonC]

20 hours ago, hiddenheels said:

Have been trying to wear one of the skirts out in daylight, but even when I had the chance, I didn't have the courage. Feelings of being a failure come back... Not just a failure to wear what I want, but thoughts of "why am I doing this to myself"... If life were a rollercoaster, at the moment I'm headed down...

Don't feel like a failure - that simply does not apply.  It's not easy to go outside the norm.  Take your time with this.  It will happen when you are ready!

[hiddenheels]

Thank you everyone for the encouragement.

SUCCESS! Was going to go to a coffee shop yesterday morning, wearing a light-brown mini skirt with dark brown ~2" heeled chunky boots, and a dark brown jacket, but just couldn't get myself to do it. So I tried again this morning. Same getup as yesterday, was going to go to a coffee shop, but again couldn't get myself to do it. I figured I'll hop into Walmart for some quick things, but sat in the car trying to calm myself. Finally ended up driving to the same store I was last week, where I bought a bunch of skirts for next to nothing, thinking I'll go through their collection systematically in detail and see if I missed anything good. By this time I was finally able to calm myself, so got out of the car, milled about for a few minutes, and headed into the store. The mall was still quiet, it was just opening up. Went into the store, went to the clearance section and spent a good 30 minutes looking at their skirts. I picked out ~10, went to the fitting room to try them on, and ended up buying 5 of them, for ~$16. So, spent about an hour total out and about in daylight in something which was clearly a skirt. Was quite freeing! No one commented or really gave it a second glance. Once I got going, the stress left me and I was quite enjoying it. They are very comfortable! And it was good to be able to be myself...

I did take a photo, but apologize, I am really uncomfortable sharing photos.

Edited March 5, 2020 by hiddenheels