Streetheeling strategies: "normal man with secret heels" vs "dressed up as woman"

[heelma]

I have been street heeling this year now many times already, even though with long breaks where I really didn't feel like it. As so many here, I always went out worrying: what others may think; will I get laughed at; what if I ran into someone who knows me; what if someone takes pictures or cell phone movies and posts these somewhere?

I posted my strategy as of so far here a couple of times already. So far, I wanted to look like a man, and I wanted to look the least suspicious and as normal and boring as possible. So, I wore men's cloths (and I had a set that I only would wear while heeling), extremely long boot cut jeans (38" inseam vs my normal 34") to cover the heels. That worked very good for me, as I posted here already. This way, I would not draw any attention to myself at all, and people would really need to look very carefully to see that I wear heels. As an estimate, 80% of all people didn't pay attention at all b/c they were too busy with their own stuff, 15% looked because they heard heel noises but didn't notice then when they looked, and the remaining 5% saw my heels. Out of those, I can count with 1 hand, maybe 2 hands now the negative reactions I actually got, and none was really very bad. (Please don't take these % numbers too seriously, I might have guessed similar but not the same in other threads in the past.)

So, this actually works pretty well.

Now, I got a bit more adventurous lately. I bought dark grey, long, wide leg women's business pants (thanks Happy Feat - those LB Lafayette pants are great!) and a grey jacket from TJ Maxx. That one doesn't fit right, unfortunately. It's a bit tight, and the sleeves are a bit too short. Maybe I'll need to check at Burlington Coat Factory. I wear a black t-shirt underneath. Now that it's Halloween time, I got a simple wig, and I bet you can easily tell that it's a wig when I wear it. It has black hair that goes just to the shoulder, and it also covers everything else of my hair, my ears, etc. In addition, I wear the biggest sunglasses I could find at Walmart; I had those actually already for the man's outfit as well. I stopped with this outfit at this point. I didn't put any make-up, etc on and won't do so in the future either. I thought that people will realize that I'm a guy if they look anyway, make-up or not; and it's too messy and too much work to put on and remove... time that I don't have. At the end, it's about heeling, not about imitating a woman as best as possible.

Ok, so I went out twice like this already. Before anybody asks: it in a bigger city north of NYC, in the business/shopping district. The first time was only for 15 min, as a test. I wore platform slingbacks from Payless, the picture is here: http://www.hhplace.org/discuss/attachments/everybody/3791d1223177314-perpetual_payless_shoesource_thread-065160_1_600x600.jpg I looked at myself when walking by some windows that kind of acted as mirrors. Hips on up ... ok, not that great, of course, but that was not really intended either. With respect to my face, I think that if people look closely enough, they can definitely see I am a guy, but with that wig and those glasses, there is no way that anyone can easily identify that it's me. And that was the whole purpose of going out in this outfit. However, hips down looked almost elegant.

Obviously, I expected to be laughed at, finger-pointed, etc etc. BUT, surprise, surprise: hardly anybody even looked. Most people were again too busy with their own stuff. A few looked up, even less turned their heads around, and no one was making fun of me. After such an encouraging first test experience, I went out again and walked for about 45 min (1.9 miles), this time with the attached Payless stilettos. Again, I really liked how the pants/shoe combo looked. This time, I really came across a lot of people, and it was almost unbelievable how few of them actually noticed. My explanation is that many people have their heads somewhere else and only see me from the corner of their eyes and identify the figure they see as a regular business woman.

Both of these heeling outfits have in common that they look as normal as possible. Obviously, the women's outfit cannot really look normal, but there are some easy improvements possible as well (mainly the jacket, or maybe a better wig). But my conclusion so far is that if one looks as normal as possible, either as a boring man with long pants (and heels that are hardly noticible) or as a not overly sexily (as a contrast to drag queens who overdo it) but rather business-like dressed woman like so many others out there, you won't raise attention of enough people to get laughed at.

The way I understand some of you here, you guys also dress up with women's pants and heels but regular men's clothes hips on up? How much attention does that raise, particularly with a skirt? My guess is that that is more striking as it is very easily recognizable as something that doesn't match all of the other everyday figures in the street?

Best of all, I now feel more open to more femine style heels, such as those pointy toe stilettos from Payless. Those are otherwise hard to hide, even with long pants. And I always thought that by looking at myself in the mirror with boring guys' clothes but hidden heels, this didn't look right. I know that many of you here think that heels should become part of normal mens' clothes. Though I certainly support this, I don't think that we are anywhere near that point yet. Particularly real girly-style heels just look awkward to me when a man wears them. When I go heeling, I want to impersonate a female outfit that I may find sexy. Even though I am happily married to a heel-loving wife (who doesn't know that I am heeling myself sometimes), I still tend to impersonate a female, which could even be her in her business outfit. Hopefully this doesn't sound too awkward now either ... but I guess there are many folks here who go out heeling for a similar reason. If so, please have the courage and try this out (if you don't do so already). I wonder what your experience will be.

I hope I can take a picture of myself in this female outfit at some point ... will be neutralized enough though that nobody can identify me.

[Dawn HH]

Heelma:-) Either way you dress, look in a mirror before you leave the house and if you are satisfied that you look the way you want to, then go out and have fun doing so. Only you know what look you are trying to achieve to blend in. Let us know what you find when out. Cheers--- Dawn HH

[HappyFeat]

As you know, I have been doing a lot of heeling recently, including experimenting with my look, where I go and how I act while heeling. The one thing I have learned is that like anything worth doing, heeling, for me at least is an evolutionary and learning experience. You mentioned that you like the LB trousers. I discovered those while heeling one day when the store manager asked if I had ever been fitted for their jeans. Frankly, up until that point I had never had what I would call outstanding customer service in any store that catered to women primarily. Sure, I would go into a shoe store, ask to try something and get it, but never had I been treated as a real customer. Since I was wearing heels that day, when I tried the pants I was stunned at how good I looked and how wonderfully their went with heels. I had gone out in a skirt a few times and worn women's bottoms before, but these were perfect for my body and looked fantastic with my heels. It only seemed logical, at least to me, that if I am going to wear heels out, I ought to wear pants that were made to wear with heels. I now own at least a dozen pair of women's jeans and pants and even have some that I wear with men's shoes simply because I like them. Though I have been going out in heels for years, it was only in the last few weeks that I have somehow, evolved beyond any apprehension at all. Always before I thought about some of the same things you had mentioned- what if people laugh, what if there is a scene, what if I run into somebody I don't want to see me, etc. Well, I still try to avoid things running into people I see, but nothing else seems to bother me. Keep in mind cell phones take crappy pictures and video. As you posted most people don't care. After experience taught me that if I go out in even very obvious heels and carry myself deliberately and confidently, a few comments or giggles aren't going to ruin my choice of how I dress. Today, after about 6 months of going out 3 or 4 times a week in heels per week I am as calm and natural as I would be in sneakers. The other lesson I learned is that it really doesn't necessarily pay to try to hide your heels or wear subtle heels. I have been noticed as many times in 2 inch loafers as I have been wearing red peep-toe pumps. At least for me, I figure that if I am going out in heels I might as well go for it and do it how I want to. Since I have developed the confidence to be myself, heels and other traditionally female articles only help me express my liberation. I think the most important thing is do what and how much YOU are comfortable with. Some guys like only inconspicuous boots, and that if fine. Some guys like to go full drag and that is fine. The most of us fall somewhere in between. But it is all what YOU are comfortable with on any given day. Also, it is easy for some people to say that you shouldn't care what people think. Of course you are going to care what people think when first starting out especially when figuring out your comfort level. If my experience is any guide, which it may or may not be, the more comfortable you become, no matter if its all guy clothes and heels, or sequenced dress with full makeup, you will care less and less about narrow minded, knuckle dragging giggles form people who have no concept of personal expression, self-actualizing, personal growth. One thing we all share in common is the desire to be ourselves and dress how we choose. Dawn HH gives the best advice- if you look in the mirror like (and are comfortable) with what you see, then just go out and have fun!

[Dr. Shoe]

Well I've done both...

[crotchboots-m]

if you need to keep it a secret,then stay home and parade in front of the mirror. if you dont care who sees you,then do it wherever. you dont need a secret plan or outfit...bah,humbug

[heelma]

if you need to keep it a secret,then stay home and parade in front of the mirror. if you dont care who sees you,then do it wherever. you dont need a secret plan or outfit...bah,humbug

Feel free to step out in heels as bold as you like. I won't.

[roniheels]

Feel free to step out in heels as bold as you like. I won't.

And that is fine. The key, like many others have said, is that you are comfortable with whatever you wear. It really doesn't matter what combinations of clothing and high heels you wear, as long as you enjoy wearing them and are comfortable wearing them. Yours is one of many experiences and preferences enjoyed by the many members at this site. Good luck on your future heeling.

[heelma]

And that is fine. The key, like many others have said, is that you are comfortable with whatever you wear. It really doesn't matter what combinations of clothing and high heels you wear, as long as you enjoy wearing them and are comfortable wearing them. Yours is one of many experiences and preferences enjoyed by the many members at this site. Good luck on your future heeling.

Exactly! I really thought that at least each of us who is around here for a while knows that each individual's situation is different, with respect why they like to heel and how openly/bold they want to do it.

[heelma]

Ok, I finally managed to take some pics of myself while being out. Unfortunately, the quality is kind of lousy, as it's from my cell phone.

I took this first set of pictures at a Payless store, where I also tried on some shoes (that unfortunately didn't fit). And why does Payless put their garbage can right in front of a big mirror at the end of the aisles?

Interestingly, I didn't get any comments while being in the store, though there were many customers in there. The store personnel just said "hello" very friendly. I am positive that people notice if they look more than just 3 sec at me, but nobody seemed to care.

I wore the Fullerton pumps from Payless (http://payless.com/Catalog/ProductDetail.aspx?&TLC=Womens&SLC=WomensDesigners&BLC=WomensDesignersLelaRose&Width=Regular&ItemCode=61536&LotNumber=064326&Type=Adult&Popularity=74&DescriptiveColor=Green ; picture is here: http://www.hhplace.org/discuss/attachments/everybody/4013d1224557261t-perpetual_payless_shoesource_thread-064326_1_300x300.jpg ) under long jeans from Avenue. For the top, I finally found a black wool jacket at target that has long enough sleeves. In addition, I wore a wig with long blond hair and a small purse from Walmart.

Sorry again for the picture quality. The heels are bit hard to see in these pictures; in the second one, I pulled up the jeans in order to show them better. Also, I would have preferred to have a picture of my entire outfit, rather than one of the bottom and one of the top.

[heelma]

After being done with Payless, I wanted to have some fun with walking platform booties from Pleaser. I still LOVE wearing platforms, though other stilettos are a lot of fun, too. The shoes are the "Indulge-560" style, black patent, 5 1/4" heel and 1 1/4" platform. In these pictures, taken in a mirror in a strip mall, I wear the otherwise same outfit as at the Payless store, just those platform booties. I am showing three pics of mine here, in order to give an idea how the outfit looks. Obviously, I am bending my knees in the one picture just to show the heels better for this picture.

[Bubba136]

What a bizar looking outfit. I totally don't like your look....Sorry!

[CassieJ]

Hard to see in the cell phone pics. Love the platforms!

[secondtake20]

What a bizar looking outfit. I totally don't like your look....Sorry!

Sorry Heelma, I have to agree with Bubba, from what I could see from the pictures it wasn't a good look. Sorry!!

[heelma]

Thanks for your comments. I know that this was not intended to look perfect. As I said, it's more about wearing heels under camouflage. I don't care if it looks good, sexy or whatever. My mission is to a) wear heels while being comfortable and I do feel more comfortable when wearing this stuff than guys' clothes with heels, prevent others from recognizing me, c) stay as cost-efficient, not to say "cheap" as possible and d) being able to "switch" from my completely normal self to such an outfit and back in the shortest possible time (which takes about 10 min for me). Sure, that wool jacket looks better with a black skirt, which I also did already. And when I wore a skirt, I did get "sexy" comments from strangers, though they were probably more likely meant to make fun of me than real. But with a similar outfit as this one, some workers on the street once said "Step back, Miss!" to me. With respect to the wig, it was the highest quality wig I could find before Helloween. I also like it because it's long and helps covering things up. Further, I don't want to mess around with make-up, as people who want to will still see I am a guy and it takes way too much effort to do it. Lastly, I know that the sunglasses look completely off, but again, this is part of my strategy to protect my identity, and this remains my top-most priority. Similarly, the gloves hide my "guy hands". So, this is all about wearing heels and looking more like a woman than like a guy with the least effort, the least expenses and the highest identity protection. I don't think that anyone who knows me could identify me based on these pictures, though I deleted parts of my face here as additional protection. Oh .... and I know that those platforms are not normal street-wear, of course. That's more for my own fun.

[Bootking]

Go for it in any way that you think best. Whether some of the other posters here like your way of dress or not, the only one that has to like it is you! Just continue doing what you enjoy doing!!

[Dawn HH]

Maybe if we could see you in the skirt, the look might be a bit different and more desirable for some here. Cheers--- Dawn HH

[Bubba136]

Go for it in any way that you think best. Whether some of the other posters here like your way of dress or not, the only one that has to like it is you! Just continue doing what you enjoy doing!!

I totally agree with Bootking. The aspect that keeps popping up in front of me is that on one hand you are totally freaked out at the prospect that someone will recognize you and your "cover" will be blown. On the other hand you dress in a manner that can't help but attract attention to you and the way you're dressed. In my opinion, if the fear of being recognized is paramount, wearing a pair of boots with heels under your jeans, with cuffs long enough to hide all of the heel except, perhaps, ½" or so, dressed as a man, would be a lot less conspicuous than appearing in public dressed the way you are in your picture.

Now, that's just my opinion....but, like Bootking, it's your opinion that counts:thumbsup:....

[heelma]

I totally agree with Bootking. The aspect that keeps popping up in front of me is that on one hand you are totally freaked out at the prospect that someone will recognize you and your "cover" will be blown. On the other hand you dress in a manner that can't help but attract attention to you and the way you're dressed. In my opinion, if the fear of being recognized is paramount, wearing a pair of boots with heels under your jeans, with cuffs long enough to hide all of the heel except, perhaps, ½" or so, dressed as a man, would be a lot less conspicuous than appearing in public dressed the way you are in your picture.

Now, that's just my opinion....but, like Bootking, it's your opinion that counts:thumbsup:....

Interesting that this misunderstanding about being recognized, etc., keeps sticking around here. I don't care if I raised any strangers' attention, in the way you suggested in your response here. That's fine, and I really don't care at all. What I do want to avoid is that if someone who knows me were around there (which is probably not the case anyway), sees me and recognizes me immediately, and I don't think that's possible, even he takes a picture.

That being said ... after having done both, secret heeling with men's clothes and going out like shown in the pictures, I largely don't see a difference between people's behavior with the one or the other. What I did see though was that if I wore stilettos or noisy heels with a guy's outfit, that some guys looked and laughed. With this one, I may get more comments, but there are many positive ones as well, which was much more rare in the other case. Think about this: you see someone just from the corner of your eyes, see woman's clothes, long blond hair and hear the sound of stilettos. Do you look up? I know, everyone here would say yes, but for another reason Many, many people don't, particularly girls. But if it's a stiletto sound in conjunction with a guy's figure, then most people think that "something is wrong".

One more comment about the jacket: most girls' coats and jackets have way too short sleeves for me, so I was looking around forever to find something that sort of fits me, that I like and that doesn't cost too much. Interesting that it's so much easier with jeans, pants and skirts.

[Dawn HH]

Heelma:-) If you are satisfied with the results of your experimentations on the way you want to dress when going out in public, then that is what you should do no matter what other people say or do. That method would not be for me, but if you like it, by all means, continue to do so. After all, it is yourself that you want to satisfy, not anyone else. That is what counts, right? Cheers--- Dawn HH

[secondtake20]

Heelma I wasn't trying to be rude or hurt your feelings, I wanted to give you a very honest answer. If you were happy with the out come, then I am very happy for you. You are the main person that you have to please and forget everyone else. The way I saw the pictures, looked like you stuck out like a sore thumb. I know how I felt back in 07 going to a costume party dressed as a woman and going in the store with 2 real women (FYI - I was very passable). I was more nervous then, than I was going out with my first planned heeling outting dressed in normal guy mode or out with my friend to dinner in 3 inch heels. Again, Sorry I was just being honest. Which gets me in trouble lots of times.

[heelma]

Heelma

I wasn't trying to be rude or hurt your feelings, I wanted to give you a very honest answer. If you were happy with the out come, then I am very happy for you. You are the main person that you have to please and forget everyone else. The way I saw the pictures, looked like you stuck out like a sore thumb. I know how I felt back in 07 going to a costume party dressed as a woman and going in the store with 2 real women (FYI - I was very passable). I was more nervous then, than I was going out with my first planned heeling outting dressed in normal guy mode or out with my friend to dinner in 3 inch heels.

Again, Sorry I was just being honest. Which gets me in trouble lots of times.

No worries - you didn't hurt any feelings. Overall, I think I don't stick out as much though, as you guys think based on these pictures. If workers on the street call me "Miss", it can't be that terrible.

That costume party comparison is a good one - that's pretty much how I look at my outfit to begin with I don't want to be perfect. I am not going to a competition. I don't want to enter something similar to you guys' "leg contest". And you guys can tell me whatever you like, this outfit is closer to outfits worn be other women on the street than what you see at "drag queens".

It's more like I go to a costume party and the other people have a hard time identifying who actually wears this costume. And in the meantime, I have my fun with it.

Street heeling is my only option; I cannot do and I do not want to do this anywhere else, and street heeling is much more fun than silently doing it at home anyway, which I also did earlier, of course.

The alternatives are either to openly wear heels with regularly guys' clothes, and this would stick out at least as much as this outfit; or do what I used to do before, which was hiding my heels under long men's jeans and otherwise wearing regular guys' clothes. This latter option shows my face openly without any disguise, reduces the options of heel types I can wear and only adds additional stress to me.

[secondtake20]

Heelma

Cool!!! Like I said from what I could see from the pictures, it looked a little rough. I am glad you are happy with the out come. I live in a semi rural area so I have to becareful of the type of shoes I wear out. I did run into a friend that I go to church with while wearing boots with a 2 & 1/2 inch heel and she said nothing or didn't notice.

As far as the costume party goes the two girls that I went with did a Great job doing my costume and makeover. I did not even recognize myself standing looking in the mirror. I was told by several who knew me as me that they did not know it was me. I know about the case of the nerves because they talked me into going into a large local chain grocery store with them to get stuff on the way to the party and boy was I scared walking in the store in fem and in 5inch heels.(FYI - No Pictures are available)

After reading more of what you have done and why, the more I understand the look. Everyone needs to be in their comfort zone. Next time if possable get some better / clearer pictures so I don't go "What The ???"

Keep on doing what makes you happy and don't care what anyone has to say, as long as it doesn't hurt anyone or yourself.

[heelma]

As far as the costume party goes the two girls that I went with did a Great job doing my costume and makeover. I did not even recognize myself standing looking in the mirror. I was told by several who knew me as me that they did not know it was me.

Great! Yes, I wish ... maybe at one point, though I cannot imagine when and how this may ever happen for me.

So unfortunately, I don't have the luxury that girls are doing my costume, and I don't have the time for it either. It has to be quick. I want to be able to quickly change from "regular" to "costume" and back, without spending 30+ min in front of a mirror to make it perfect, to apply make-up, etc. This all has to happen in a car seat within 10 min! Heeling is the main objective.

And then, as I wrote before - even IF I made this outfit look perfect, I would still be easily recognized as a guy by people who really care to look closely, which is far less than 10% of the people I run into on the streets. So, is it worth the effort? Clearly not. As in so many things in life, you can get to 95% of a target quickly, but if you want to reach 99% or more, you really have to spend a lot of time and energy on it. Same here.

Another thought: Think of the thread posted some time ago here about fears of being caught on security cameras, cell phone videos, etc. By hiding enough of what helps people identify me, I don't have to worry about that anymore. All they can see of me are some non-unique parts of my face (that's why I have those big sunglasses on). Let people take their cell phone videos, have their fun about it and post it wherever they like - nobody will guess that it's me. So, let them laugh at this stranger in a woman's costume: they don't laugh at me.