Public Heeling: What Boundaries Do You Cross?

[freestyle75]

Hi everyone!

Since I started heeling a few years back, I became more bold with time, partly also because I read blogs and forums like these. Still, there are boundaries that I thought I wouldn't cross when I started, even when I am just looking back to the beginning of 2012.

The beginnings in 2009: I started out with a a medium block heel ankle boot, designed from Christian Dior for men. Interestingly enough, the heels of these boots make a very recognizable "tock tock" sound, similar to women's heels, whenever you walk in them. When I first walked with these in public, I noticed that only few people will actually look at you. I even wear these boots to work, and nobody cares. The *only* reaction where someone actually asked me about the boots was when I was shopping at a fashion store and the gay sales assistant was literally blown away by the boots and wanted to know exactly where I got them.

Christian Dior men's heels

But I digress... so... first boots: Men's heels, block heel, 4.5 cm (1.8 in).

Going higher: I became bolder and asked my cobbler to make a pair of boots for me, still with a block heel, with 7.5 cm (approx. 3 in). I was astonished how well I could walk in them - after all not that surprising, considering that they were custom built for me.

Custom built heeled boots

I became interested in how high I could go.

A few months later, I bought Rick Owens men's heels with 9.5 cm (3.75 in) and still was doing fine. Similar to the Dior-boots, nobody cared.

Rick Owens men's heeled boots

Up to this point, I had only bought heels made for men. I had previously told myself not to buy footwear sold in the women's department, as I would cross a line that I didn't want to cross.

First women's boots: Still... my question "how high can I go" hadn't really been answered till I found the "Anabela" boot from Alexander Wang. I looked at the picture of the boots and just had to have them.

I got a brown pair during a sale at a huge discount. Apart from the fact that these boots run small, the heel has a whopping 14.5cm (5.7in), which puts this boot at the top of my collection in terms of heel height. Despite the 3 cm (1.2 in) platform, the boots are very difficult to walk in. When I searched online for blog writers, I found that the few girls that had bought this boot also struggled in walking in them properly. Up to the current day, these boots have stayed mostly in their box, due to the fact that I cannot walk in them properly.

Alexander Wang impossible-to-walk-in-boots

I had found the height which would be too high, but at the same time I had also crossed the line - I had bought the first pair of women's boots. I found that even designer boots for women were often cheaper than the men's designer heels I had bought. So I looked for more boots that were styled similar to the men's style: Always with a chunky block heel, but sometimes still with a very high heel, e.g. the ones from Costume National.

Costume National boots

New heel types: Things changed when I saw a picture of Charles Guislan sitting on a wall with wedges (presumably Rick Owens). I wanted those wedges too! -- During a London visit, I bought the Rick Owens wedges, in a knee-high style, as the ankle boots were sold out. I found that I wouldn't really wear this style, because it was knee-high, so I looked for another pair and settled with wedges from Ann Demeulemeester. Later I bought additional ones from Jil Sander, which are still among my favorite boots.

left: Ann Demeulemeester wedges, right: Jil Sander

I had moved from low block heels, to high block heels, to high wedges - all at ankle height. Wearing these in public was quite easy, as my trousers covered most of the heel anyway.

Knee highs: Things changed during a London visit, when I visited the world's largest shoe store (at least that's what they claim at Harrods). I spotted a pair of AF Vandervorst knee high boots with a medium heel that I instantly fell in love with. With these boots, I also started wearing "jeggings", so I could fit my trousers more easily into my boots.

Suddenly I was wearing knee high heeled boots - and I had expected some reactions from people, but I didn't get very much. Maybe because people think it's an equestrian boot, I don't know.

AF Vandervorst boots

Up to this point, I had broken most of the self-imposed barriers. How feminine do I want my footwear to be? The last frontier (at least for me) were stiletto heels. Again, I had spotted a picture of a guy wearing stiletto pumps (pumps!) in a blog, and I was surprised how good this looked. Should I get stilettos? No. This would go to far, right? Or would it?

Stiletto: I spotted two pairs of boots with a stiletto heel that were marked down quite heavily - and bought them. When I brought one of these (with a leather sole) to my cobbler to get a protective Vibram rubber sole attached, he looked at the boots and said "that's too narrow", pointing at the heel (that's the left pair in the picture). He has seen most of my other boots and was totally ok with it, but at this point, I realized that I might have crossed a boundary that I shouldn't have crossed. I have bought these boots just two weeks ago, but haven't worn them yet.

left: Graffiti boots, right: Buffalo

Now to the initial question of my post:

For those of you that also wear their heels in public:

Have you seen this kind of "development" in yourself as well? Have you gone higher and higher, or moved from a more block-ish heel to a stiletto one? What type of shoe would you consider off-limits and would not wear in public?

How would you describe your general outfit when wearing heels? All male or mix of female + male items?

[mlroseplant]

I've only been wearing heels publicly for half a year, but yeah, my tendency is to go to a stiletto. I'm not at all there yet, as I don't think I look good in stilettos. I have bought some thinner heels recently, but nothing that you could call a stiletto. Other than shoes, I don't have a desire to wear anything "feminine." I do have a desire to look good, though. ^^

[SleekHeels]

If I made such a transition it was really very rapid, progressing from discrete, closed style wedge boots through to wedge sandals or courts with stiletto heels in just a few outings, just as a way of building confidence. Now I feel I don't have any boundaries in terms of heels being "too feminine" to wear, if I like a style I'll try to find a way to wear it. I just find myself wanting to back off from looking like I'm trying to "pass" as a woman rather than a guy comfortable with expressing femininity.

[Steve63130]

Although you've come a long way in pushing your envelope, Freestyle, you have restricted yourself to boots. So even though you've gone to higher and thinner heels, you haven't gone to pumps, sandals, clogs, loafers, or other styles. Many of us here have, some in private, some in public. I have gone public with all of these styles but I've not crossed the boundary to wear stiletto heels. I think stockier guys like me just don't look good in stilettos. That's just my opinion, but I don't feel comfortable if I don't feel I look good. So I'll leave them for the skinny guys, like Radiodave, for example. He looks great in stilettos. We're all somewhere on the spectrum of progression from masculine to feminine characteristics in our footwear. There is no doubt some reserve to what is worn in public. I am sure a lot of guys tend to wear footwear that is more toward the masculine out in public and less so in private. But even in our wardrobes, some of us have a wide variety of styles and others have a narrow slice, like you focus on just boots. Anyway, you posted an interesting topic. Thank you. Steve

[dbert]

Strangely if anything I've gone the opposite way to you. The first heels I really wore in public were much more similar to your final pairs of ankle boots. More recently I have actually gone up a step in your evolution to wedge boots that I can pretty much wear without anyone noticing at all.

[niknhose]

The only boundary that I have yet to cross is color. My heels vary from blocks to wedge to stileto to cones and most of my heels are black. I have recently purchased a couple pairs that are colored. A pair of red patent pumps and a pair of purple/pink platform heels. I also make no attempts to hide my shoes either. I wear my pant legs rolled up to my ankles so my shoes are in full view. Nikki

[Histiletto]

Hey freestyle75, I enjoyed reading your systematic approach to finding the type of heels and height that you can be comfortable with. The comments that have come after are also food for thought. Wearing heels should not be seen as a gender display, but we have been programmed to think in these terms. If we have desires to wear particular styles then it is our right to make those choices for ourselves and other people are going to learn they have the same rights, too. The idea that someone else knows my desires better than I, is a violation of individual agency. We are all unique beings of the human race with our own set of opinions, desires, talents, and perceptions. People may be able to come close to similar understandings, but others still can't totally know another person's data processing system for it is only that person's and others have developed their own, just because we are individuals. A child will follow a system until they don't agree with their perceived reward or outcome and only they know the point of friction or fiction to them. So it is with grown-ups. When something doesn't fit right then there must be something wrong. Is it the concept or the way it is being applied? As a guy, I like to wear stilettos. Does this mean I have feminine tendencies or is the attitude toward my desire ill-conceived? What about the women who choose not to wear heels? Are they exhibiting their masculine side? These type of personal choices are the responsibility of each individual to decide, not by their parents, siblings, neighbors, acquaintances, associates, or the efforts of some social groups. Now the parents have the opportunity to present and introduce wardrobes to their children, but the decisions for what they desire to wear can't legitimately come from anyone else. I like tapered block heels that look like they are the beginning shape of spikes when they are less than 5cm high. Any higher heels, I prefer spikes and stilettos. I have hardly ever invisioned any other type of heels to be in my choices. When I have considered the more massive heels like those worn in the 70's, they remind me of the usual cartoon high heeled characters, like Minnie Mouse. Those type of heels seem to increase the size of the wearer's feet to outlandish proportions for the body they support. Add to this look the use of platforms and the wearer's feet look like small high cliffed islands, each supporting one palm tree. They might as well have worn 5 gallon buckets for footwear. I realize I'm exaggerating this look quite a bit, but this is how I perceive and feel when viewing most other heels that aren't spikes or stilettos. Everyone has their own opinions and desires as to how they piece life together. To those that enjoy the blocks, wedges, blades, and etc., I support their choices and I'm happy that they are wearing the styles they feel good with. In arriving to stilettos, there was hardly any transition from a child's Mary Janes. Once I saw the thin spike heel pumps, they became my utimate quest in footwear. Then came the stilettos, which later became synomymous with spikes and people began to refer to both as stilettos. In wearing these type of heels, it has been mentioned that the wearer needs to be somewhat trim. I tend to be a bit heavier than most stiletto wearers are perceived, but that helps me to stray active and reduce the obese potentials.

[ilikekicks]

Now to the initial question of my post:

For those of you that also wear their heels in public:

Have you seen this kind of "development" in yourself as well? Have you gone higher and higher, or moved from a more block-ish heel to a stiletto one?

No. I went from sneakers/work boots into Stilettos. I was NEVER into shoes in mensware at all.

What type of shoe would you consider off-limits and would not wear in public?

' Pleasers ' or stripper shoes. There are many reasons for such. Basically ANY high platforms or something that screams to most around me ( usually men ) ' Im cheap '. Such goes for almost all the things I wear outside of my former work clothing.

I wear heels around the guys ( friends ). They really dont mind but when the ' stripper shoes ' types come out, their attitudes and reactions always change to VERY negative. So I dont go out in public with such attire on. I have before and may again, but its far from a regular thing. I dont want to be bothered and Im not looking for any attention. My comfort zone is mostly being left alone, thus I dont really TRY to wear something that sends a screaming message to those around me or within eyesight.

How would you describe your general outfit when wearing heels? All male or mix of female + male items?

Mixture of both, more andro then anything else. Mens pants dont fit me all that well, neither do their shoes ( I have narrow feet ).

[Heel-Lover]

I've been wearing heels publicly for 10 years. My heels had evolved in the first 2-3 years as others have, as I gold bolder my heels got higher and skinnier. I like the look of heels and ankles and legs so I tried skirts and skirt suits for work etc many many years ago. That worked well for me and I became quite comfortable with that look. Nowadays most of my heels are stilettos, very high and are 'pretty' shoes - not 'stripper' shoes. My heels are delicate, trendier and are mostly pumps/ peeptoes or slingback styles. A handbag then became an accessory. The handbag was a really hard transition, I found it harder to work than the step into wearing heels in public! I needed a handbag because the tailoring I had on suiting etc just doesn't accomodate carrying stuff in pockets The handbag is the hardest transitional step I have made. - it was one I recall as the most uncomfortable. Probably because you use your hanbag so much, you handle it all the time and it was quite awkward. I am comfortable with handbags now - and I really enjoy the coordination possibilities they add to an outfit. I have also evolved into colours in my shoes, whites, blues, greens, reds, orange, pinks, leopard, yellow, creme, suedes, glitter, shoe ornaments, neon green ... the list just goes on and on and I have different uppers from patent, to croc, std leathers, suedes, brogues, cut-outs etc....I enjoy wearing a simple outfit and 'popping out' a pair of bold statement shoes. Over the next 2-3 years of wearing skirts the styles changed. I became comfortable enough to wear high hemlines and different styles from a-lines to pencil skirts. In the last 12 months I have worn dresses, initially as an experiment but being astounded at the convenience and simple style of a dress I am hooked. I have bought 10 dresses this year. I have found there is little difference in wearing a jacket over a dress than wearing a jacket over a skirt and top...and the dress is simply easier, comfier and stylier. What wouldn't I wear? Fishnets, leather skirts/ jackets - the sort of attire that says 'Trashy' or 'Drag' or 'Hooker'. How do I see my style? I would say a crazy mix of male/female. I am a bloke wearing womens styling. I make no attempt to hide that I am a guy... 95% of people I meet actually get it. Cheers Heel-Lover

[JeffB]

Well, regarding my personal heeling development, like freestyle75, I began with two inch, block heeled loafers which I had been most comfortable with in the beginning of my journey. From there, I graduated to block heeled ankle boots, I found that I liked boots like those a lot and wore them often. As my evolution continued, I found myself curious about pumps and thinner heels, so I moved on to those styles, as I did, going from two inches to three and then four, I discovered that spiked heels were seriously cool and I didn't want to wear anything else. Block heels are a distant memory for me today. I was particularly enamored by plain black pumps, the first time I wore a pair, it was literally love at first sight and they became my favorite shoe style. In fact, seventy-five percent of the shoes in my collection are black pumps which can worn with practically anything and everything, be it casual or dressy, and I'm always in the market for more.

It took awhile to warm back up to boots after my love affair with pumps began, I started with ankle boots from Payless in the early 2000's, then moved up to my first pair of knee high boots around 2005 or so and found them to be attractive. Today, I have two pairs of knee highs, one from Payless I've had since 2008, the others, a pair of four inch Pleasers I bought a year or so later, both of which I wear frequently in the fall and winter. Now we come to thigh high boots which I was introduced to here at HHPlace by thighbootguy. Reading his many adventures and outings in thigh highs intrigued me greatly as I thought he looked good in the boots he wore in photos he displayed. So, I decided to take the plunge and bought a pair of my own, in a word----WOW!! The first time I pulled them on, I was overwhelmed by how sleek and alluring the boots were, and in an instant, I understood TBG's love affair for thigh highs.

Next, we come to clothing. Originally, I wore men's clothing with my heels, thinking that was the only way to go, and I was perfectly content with that. However, over time, I came to realize that it wasn't enough to wear just anything with my shoes, I needed to look as stylish as possible as I wanted my clothes to look as nice as my footwear, but I came to acknowledge that men's clothes weren't nice enough to suit my needs, so I gravitated to the women's side of the store for what I wanted, starting with tops and jeans, followed by that first experiment with skirts in the fall of 2008. The first time I wore a skirt in public was such an incredible rush, I was sold on them instantly and I've been wearing them regularly ever since, everything from 17 inch minis to floor length maxis and everything inbetween. Finally, my first foray in a dress in 2011, once again, I experienced a rush that led me realize how much fun it is to wear them.

The final part of the equation are handbags. Not too long ago, I was content to stuff everything in my pockets when I went on outings, something that looked wholly unattractive, given the bulges and all, but as I gravitated more and more towards wearing skirts and finding myself annoyed with their inherently small pockets, I arrived at the conclusion that I needed to carry a bag to put my stuff in. My first choice was the gender neutral Buxton Bag I bought at a drug store, and, at the time, that was good enough for me, but then, I started gravitating towards more feminine looking bags, in other words, purses. Since I was regularly wearing skirts and heels, to agonize over being seen with a purse was patently ridiculous, so I started buying and using them on my trips, even when in jeans, I carry a handbag which has become as natural to me as the clothes and shoes. In fact, I wouldn't be caught dead on a jaunt without a purse.

What wouldn't I wear? Mules for starters, I've never liked them as I consider such shoes to be woefully impractical. I'm no fan of sandals, peep-toes or platforms, what's more, I NEVER wear any heel height over five inches as I do a lot of walking on my outings and need to be comfortable. In closing, I am no longer just a "heeler", I've evolved into what I consider as being a full-blown "freestyler", a man who openly and proudly wears women's clothes and shoes in public as a man. Let me emphasize those last three words----AS A MAN. I have no interest whatsoever in donning wigs, makeup or fake breasts, all I want to do is wear the clothes and shoes, like Heel-Lover, I don't hide what I do, I'm right out there for all the world to see, boldly and confidently.

[freestyle75]

Thanks everyone for your answers!

Even now that I've been wearing heels for three years now, I guess Histiletto is right when pointing out that it is one's right to wear what I want to wear, with no exceptions.

Then again, all of those men that are on this part of forum are biased when it comes to the question if you can cross a line that you "should not" cross. For every strange kind of hobby or likes, there is an online forum. It may sound negative, but I don't mean it that way. Quite contrary: I am happy that there is a place where one can discuss things like these, as I have no one to talk about me wearing heels. Nevertheless, I often wonder whether I would have gone that far without the internet (and the pics of the fashion shows from Paris and London that I saw, which made me wonder why I couldn't wear something like this, too).

The one thing that seems to be common is that some wouldn't wear "stripper" shoes in public. Again, quite an interesting observation: While I was browsing one of the high-end online fashion boutiques, I found some boots by Yves Saint Laurent, which look similar to the stripper ones by Pleasers. Price difference: ~ 1,500 USD (if you are buying full retail). So one couldn't say that it's a "cheap" look if you are walking around in those YSL boots, although it's a "cheap look" if you don't know that they are YSL

@Steve63130: Yes, I mostly have boots. I didn't mention two sandals I bought during summer. One pair from Tommy Hilfiger, which I haven't worn at all, another from Fendi (this is my pair), which I have worn maybe one or two times. I don't know how to put it, but boots are still more "masculine" for me compared to sandals or pumps. After seeing the guy with the stiletto pumps in the blog, I bought pumps from Steve Madden, which a) fit too tight, looked a little silly (at least in my opinion). Apart from these, I do have some styles that are similar to a loafer. Personally, I find that boots provide the best foothold (don't know whether that's the correct translation), meaning that they are much easier to walk in with high heels than compared to pumps, at least that was my experience with the not-so-well-fitting Steve Madden's.

My posting would have become too long if I mentioned every try-and-error I've made along the way

@Niknhose: Hmm... color. That's also something where I am still very conservative. Black, brown, light brown... apart from the red soles of my Louboutins, I don't have any other colored shoe. Also when it comes to materials, I just have real leather or suede. I am currently considering a pair of patent leather (ankle) stiletto boots - at the same time I am asking myself where I would wear them (not very often), so I am still waiting for the sale to start. Either I get them at a discount, or I don't buy them...

Regarding pants: I have jeans with different lengths, so I cover about half of the heel height. Sometimes I am still unsure how much should be covered and how much should still be visible...

@Heel-Lover: I have a few handbags too, although many of them are the "messenger" bag type where you have a diagonal strap running across your shoulder/waist. I've seen one bag by Proenza Schouler that I really like, which I haven't bought so far because it is really expensive. Apart from the tailoring, I just think that it doesn't look good if you have stuffed pockets... keys, smartphone, wallet... this all needs to go somewhere.

Dresses: I haven't bought any dresses, but have sewn a longer top on my own which was based on a dress design. I often combine the longer top with skinny jeggings and knee-high boots.

@JeffB: I also consider myself a "freestyler", although I often find that I still think too much about what others will think of me. That's why I restrict myself to things that other men probably wouldn't touch, but which aren't too feminine for my taste.

[NewfieGuyInHeels]

I've always said that I would never wear my heels on full display. Now I find myself wearin flat knee and thigh high boots over jeans on a regular basis, and I'm now looking at wedge boots to do the same. I have my eye on a couple so if I get them during the Boxing Day sales ill post pics.

[mlroseplant]

I've already crossed some boundaries that I didn't think I'd cross, and one of them is wearing some 5 inch heels with a pretty thin heel (but certainly not a stiletto). A month ago, I could not have imagined wearing such shoes out. It would be very difficult for an ordinary person off the street to find these very masculine, but maybe I'm going a little nuts right now, since I've gotten either no reaction or positive reaction so far to my choice of footwear. For right now, I really can't imagine wearing high heeled sandals. I prefer going barefoot in the summer. Maybe that's why people don't say much about my heels. I'm already an oddity with the bare feet. Maybe they just figure, "Hey, that's just James." My line that will never be crossed? Wearing short shorts with Candie's type mules. Would love to do it. Ain't never gonna happen. Ever. I don't want people to look at me at say, "Ewwwwww!" LOL

[ilikekicks]

Thanks everyone for your answers!

The one thing that seems to be common is that some wouldn't wear "stripper" shoes in public. Again, quite an interesting observation: While I was browsing one of the high-end online fashion boutiques, I found some boots by Yves Saint Laurent, which look similar to the stripper ones by Pleasers. Price difference: ~ 1,500 USD (if you are buying full retail). So one couldn't say that it's a "cheap" look if you are walking around in those YSL boots, although it's a "cheap look" if you don't know that they are YSL

The only people whom would know those are YSL would be people whom follow clothing. They could have red soles and be made by CL and most people would still look and say ' those look like pole dancers shoes '. Thus its not a pocketbook ' cheap '.

When I went to buy car parts, the guy behind the counter said ' can I help you miss? '. It doesnt mean Im female, just how I looked at the time.

The perception of 2inch or taller platforms usually goes to Porn, Strippers, Streetwalkers.. It doesnt matter the cost or whom makes them, people will judge the person wearing them without even saying ' hello '.

[Guest]

today I wore my black boots (the ones in the avatar pic, dont remember the name of 'em @ the moment) & I love them, but I REALLY need to get some insert soles so my feet can be more comfortable-there about 3 inches, the max I can wear these days now.

[hh4evr1]

I used to wear block heels only in public but have also worn stilettos. My boots and shoes had always been black now I like other colours.

[Guest]

today I bought some support pads for the ball of the feet (the upper part next to the toes) so I think that this should fix the problem I was having yesterday while wearing the boots in my avatar (they are from NOT RATED) in any case I'll give them a try to see if thats the right kind of support needed for my feet while wearing these boots.

[JeffB]

today I bought some support pads for the ball of the feet (the upper part next to the toes) so I think that this should fix the problem I was having yesterday while wearing the boots in my avatar (they are from NOT RATED) in any case I'll give them a try to see if thats the right kind of support needed for my feet while wearing these boots.

I have them in all my boots and they do work. A worthwhile investment.

[HappyinHeels]

freestyle75, What a nice visual array you have given us of your progression from the earliest lower heels to the later higher heels. I think what caught my attention more though are the even more impressive prices you have been paying for your boots. You are certainly fortunate enough to have the kind of job to allow you to buy such high-end footwear. Now the burning question I have is have you ever had an urge to go visit the La Piazza shoe store near Dusseldorf? THey are known for platfrom sandals but the qulaity is magnificnt and the prices are quite high as well. By the way I think black is a cool color, we all like it here, and it is natural starting point in footwear. Thanks again for the wonderful photo selection. HappyinHeels

[ilikekicks]

Thanks everyone for your answers!

Even now that I've been wearing heels for three years now, I guess Histiletto is right when pointing out that it is one's right to wear what I want to wear, with no exceptions.

Very true. You also have a right NOT to wear something you dont want. It goes both ways and thats the glory of real liberty. The theme of ' The only thing stopping a guy from going out in a pair of heels is them not putting the shoes on ' is very true.

Then again, all of those men that are on this part of forum are biased when it comes to the question if you can cross a line that you "should not" cross.

My approach is a bit different.

MANY of the men whom post on this site speak of their girlfriends/wives and others in their lives not appreciating them going out in heels or their wearing of them. Maybe if it was ' toned down ' a bit.

An example : If a guy were to wear a pair of classic pumps -vs- pleaser hookers..

As men, we might like seeing women in those hookers and think nothing of it. Women have a stigmatism and always judge each other. They are CONSTANTLY sizing up their ' competition '. We have heard from several women on this site that they dont want men in heels for many different reasons. One even stated they believe if men were to get into the market, it might change the whole ' heels ' concepts ( Competition! ).

Wives and girlfriends might not care for hookers/strippers/porn or things that make women look like nothing more then a sex object.. whats usually on their feet? Monster platformed pleaser shoes..

Now we are their boyfriends, husbands, regular friends.. does anyone REALLY think a woman would want to be seen with a man in such attire? Really?

If people think Im wrong, just look at what our wives tend to wear or go out into a mall or something and take a visual que/tally.

Thus, when Im going to go out, I try to wear what I want SO LONG as the bridge I dont cross is the one that might upset her ( wife ) .

Im fortunate enough to have a wife that goes out and BUYS me shoes, let alone doesnt mind me wearing them at all.. BUT! I wish to keep things within reason. Respect goes quite a ways.

For every strange kind of hobby or likes, there is an online forum. It may sound negative, but I don't mean it that way. Quite contrary: I am happy that there is a place where one can discuss things like these, as I have no one to talk about me wearing heels. Nevertheless, I often wonder whether I would have gone that far without the internet (and the pics of the fashion shows from Paris and London that I saw, which made me wonder why I couldn't wear something like this, too).

Ive never really given this much thought. I came here as a flat footer outside of halloweens.

The one thing that seems to be common is that some wouldn't wear "stripper" shoes in public. Again, quite an interesting observation: While I was browsing one of the high-end online fashion boutiques, I found some boots by Yves Saint Laurent, which look similar to the stripper ones by Pleasers. Price difference: ~ 1,500 USD (if you are buying full retail). So one couldn't say that it's a "cheap" look if you are walking around in those YSL boots, although it's a "cheap look" if you don't know that they are YSL

A lot of people wouldnt know what ' YSL ' is ( nor Pleaser for that matter ). If its not in the local Walmart or a sporting goods store, they couldnt care less.

I would believe 99% of the people seeing that pricetag would laugh their ass off and say ' Theres a lot of others things I would spend 1500$ on before a pair of boots! '.

It wouldnt matter if its YSL, King Kong or SantaClaus on the nametag of the product. Cheap looking is ' Cheap looking '.

One of the reasons I usually wear either my wedge booties or a ' classic pump ' is because people whom wear heels all have a pair of ' classic pumps ' of some kind. No fancy lace or dangling items. A normal sole and not a jack-stand platform.. Its something that has been and can still be appreciated.

If someone is crying about their footware and not being accepted as a ' guy in heels ', it might not be the fact they are male.

[Curt]

So what you're saying, every brand make pornstar heels. How high does a platform have to be to be defined as a stripper shoe. I have a pair of knee boots with concealed platforms of 1.5" and 3.5" heels, but looking at them, you can tell right away they are platforms. I. Also have a pair of pumps with 1.5" plats with 4.5" chunky heels, I think they look very hooker-ish. But I love wearing thgem, even to formal events. I don't have any boundaries when out and about. In into high fashion and its commonplace to dress the way the designer intended it to be. A few canadian designers are breaking down boundaries in terms of what they would like to see people wear. I say people because there is no difference in gender in the collections they bring out. Fluevog brought out a few heels for men, but aren't very sultry like the womens ones, and they actully enjoy selling womens shoes to men. Most of their women's shoes could pass as unisex in the high fashion circles. Rad Hourani is a canadian designer that has male and female models strutting down the catwalk in the same 6" heels, leather leggings, and long fitted coats. They look awesome, but too expensive for my budget. What I'm getting at is, if designers had made clothes that everyone could afford, them there would be no boundries.

[freestyle75]

Hi everyone,

first of all: Merry Christmas!

Interesting that my YSL / stripper example received so much attention. I think ilikekicks way of looking at it is a very good one. Apart from not wanting to upset your wife/girlfriend, I guess if we really want to get people to accept men who wear heels, neither the YSL (at least the type shown) nor the Pleaser-boots are a very good choice. By the way: I have not bought the YSL boots

@HappyinHeels: About the prices...

When it comes to regular "office" (work) shoes: 10 years ago, when I had to buy men's shoes, I would go to my local shoe store - which carried a German brand most men wear in the office - and bought a pair at around 200-250 USD. At that time, this price was quite high for me, so when a pair literally fell apart after just one year of wearing it, I took it to my cobbler to ask him whether he could repair it. Despite having a leather sole & upper with stitching all around, he told me that this pair could not be repaired and had been assembled in the cheapest way possible. He asked me whether I still wanted to try to get it repaired elsewhere or whether he could tear it apart and show me what he meant.

He disappeared shortly, tore the sole off the shoe and came back to the front counter to show me: There was a very thin leather sole, then there were several layers of CARDBOARD paper, and then there was another thin leather insole. The stitching was fake, most of the shoe had been glued together. This was when I got interested in how shoes are made, what the differences in materials are, etc.

I asked my cobbler which brands he could recommend, shoes that were actually still made in a way that you had great leather, a Goodyear construction and the possibiltiy to take them apart and get them resoled without discovering that you had bought cardboard paper shoes.

Since then, I've switched to shoes from other manufacturers - not designers - for my office shoewear that were recommended by my cobbler, who also creates shoes/boots by himself. Most of the pairs I own run between 500 - 650 USD and do have a good quality. Still, for me these kind of shoes are "work" shoes - they get frequent wear, so I am not willing to invest in custom made shoes, which also don't last longer. Every shoe gets creases at some point, and will look aged even with a completely new sole/heel.

When it comes to heels: Apart from the Dior heeled boots, which are ok for the office, I don't wear any heeled shoes/boots in the office. This is a line I will never cross, as I know what is expected. So for me, all shoes with heels are a kind of a hobby, with me being a sort of a collector. I earn well, but I also know that I've spent way too much on shoes lately. Well, not only shoes, but fashion items in general. Especially in the last few weeks, I've gotten so many emails from really expensive stores that give you 30% to 70% off, sometimes even with a private sale before anyone else gets the discount. I've developed into a "shopoholic" lately, which is not a good thing. One of my resolutions for 2013 is to spend less on fashion. Something only a guy does: I've put together an Excel-spreadsheet that shows every purchase (not only shoes, but also other fashion items). I am currently at 62 pairs of shoes (actually a bit more, but I've only listed things since late 2009), at an average price of 505 USD, at an average of 15% off.

I have browsed regular shoe stores, but often don't find what I am looking for. Each and every model that I own has been something that we call in German an "aha Kauf" (aha buy). You walk by a store, see a pair and go "wow, these are beautiful/cool/unique, I got to have them". I've even "hunted" down pairs that weren't available in my size across the globe (got them shipped from the US, UK, Italy, France, Spain, Belgium).

That's what I also like: When you meet me on the street and ask me about the stuff I wear, most of the items come with a story. The sales-clerk that was so confused by a guy buying shoes, that she accidentally put a wrong sized shoe in the box (which I discovered back in the hotel and had to drive back to the store); the pair that I saw in London (not my size), which I hunted down in a small boutique in Belgium; the coat that I had searched for for weeks both off- and online, but couldn't find it anywhere, till I finally got a hint in a forum that a small Italian boutique would currently sell that brand at 50% off ... they had one piece of that exact coat still available in my size.

It may sound crazy, but this makes fashion special for me. It's not something that I got "somewhere" that I don't have any relation to. It's something that comes with a story, that is personal to me, something I really like. Sometimes the item reminds me of a shopping spree with a good friend or a great vacation.

About La Piazza: No, I haven't been there so far. I have looked at their website, but I am not sure whether I like the footwear they offer. At least from what I've seen on their website, there wasn't a pair that I would have liked in my collection. Sorry!

@Pumpcat: I actually held Rad Hourani's signature boots (with the square toe box) in my hand at a small boutique in London - unfortunately they weren't available in my size. When I walked through the shoe department at Harrods later that day, I discovered a similar (women's) boot by Acne (still available here). Luckily they still had them in my size, so I got them right away :-)

Regarding Fluevog: I've seen them online, but have read mixed reviews on the quality of Fluevogs. Besides, I am not sure about the sizing. Do you own any Fluevogs? What do you think of their quality?

[ilikekicks]

Hi everyone,

first of all: Merry Christmas!

Interesting that my YSL / stripper example received so much attention. I think ilikekicks way of looking at it is a very good one. Apart from not wanting to upset your wife/girlfriend, I guess if we really want to get people to accept men who wear heels, neither the YSL (at least the type shown) nor the Pleaser-boots are a very good choice. By the way: I have not bought the YSL boots

I have a very small idea of what Im looking at. Most guys would just brush it off as a 40$ pair of boots you could buy at a local department store/mall.

I have browsed regular shoe stores, but often don't find what I am looking for. Each and every model that I own has been something that we call in German an "aha Kauf" (aha buy). You walk by a store, see a pair and go "wow, these are beautiful/cool/unique, I got to have them". I've even "hunted" down pairs that weren't available in my size across the globe (got them shipped from the US, UK, Italy, France, Spain, Belgium).

I happened into the same ' aha kauf! ' with my favorite pair of ankle boots. I just saw them and had to have them. I havent done any global hunting, but if something comes up that I really do like, I will hunt things down.

That's what I also like: When you meet me on the street and ask me about the stuff I wear, most of the items come with a story. The sales-clerk that was so confused by a guy buying shoes, that she accidentally put a wrong sized shoe in the box (which I discovered back in the hotel and had to drive back to the store); the pair that I saw in London (not my size), which I hunted down in a small boutique in Belgium; the coat that I had searched for for weeks both off- and online, but couldn't find it anywhere, till I finally got a hint in a forum that a small Italian boutique would currently sell that brand at 50% off ... they had one piece of that exact coat still available in my size.

It may sound crazy, but this makes fashion special for me. It's not something that I got "somewhere" that I don't have any relation to. It's something that comes with a story, that is personal to me, something I really like. Sometimes the item reminds me of a shopping spree with a good friend or a great vacation.

Uniqueness. You like having a Uniqueness about what you wear and how you wear it. Thats admirable.

Be well!

-Ilk

[Puffer]

...

I had found the height which would be too high, but at the same time I had also crossed the line - I had bought the first pair of women's boots. I found that even designer boots for women were often cheaper than the men's designer heels I had bought. So I looked for more boots that were styled similar to the men's style: Always with a chunky block heel, but sometimes still with a very high heel, e.g. the ones from Costume National.

Costume National boots

...

At the risk of sounding patronising, freestyle75, may I commend you on a very clear, literate and interesting account of your progression - and very well illustrated too! (I think you should give lessons to those who aspire to posting on this board and elsewhere.)

I like many of your boots, although not really keen on those with significant platforms. The Costume National boots (above) look great - how high are the heels/platforms, please? I've never heard of them and imagine they are quite expensive.

...

I like tapered block heels that look like they are the beginning shape of spikes when they are less than 5cm high. Any higher heels, I prefer spikes and stilettos. I have hardly ever invisioned any other type of heels to be in my choices. When I have considered the more massive heels like those worn in the 70's, they remind me of the usual cartoon high heeled characters, like Minnie Mouse. Those type of heels seem to increase the size of the wearer's feet to outlandish proportions for the body they support. Add to this look the use of platforms and the wearer's feet look like small high cliffed islands, each supporting one palm tree. They might as well have worn 5 gallon buckets for footwear. I realize I'm exaggerating this look quite a bit, but this is how I perceive and feel when viewing most other heels that aren't spikes or stilettos. Everyone has their own opinions and desires as to how they piece life together. To those that enjoy the blocks, wedges, blades, and etc., I support their choices and I'm happy that they are wearing the styles they feel good with.

In arriving to stilettos, there was hardly any transition from a child's Mary Janes. Once I saw the thin spike heel pumps, they became my utimate quest in footwear. Then came the stilettos, which later became synomymous with spikes and people began to refer to both as stilettos. In wearing these type of heels, it has been mentioned that the wearer needs to be somewhat trim. I tend to be a bit heavier than most stiletto wearers are perceived, but that helps me to stray active and reduce the obese potentials.

I agree with you, Histiletto, about 'Minnie Mouse' shoes (high thick heels and/or chunky platforms) and how unflattering they are. Leaving aside male wearing, I also agree with you that stilettos are a the preferred style for sheer elegance, although slightly tapered block or cuban heels look good too, on either sex. You imply that 'spike' and 'stiletto' heels are not the same, although both are usually referred to as stilettos (and spike heels are not really recognised as such in the UK). What is the difference between them, please, in your view?

[Curt]

I think spike heels are unique to having steel tips. I like plastic or rubber tips. But spike and stilleto heels are very similar. I cross another boundry! I walked all day in ugly boots, I mean ugg boots, with my pants tucked in them. Toronto is a good city for heeling. I saw three guys with pants tucked into knee boots within 10 minutes. That's my next challenge, to wear high heel boots with the pants tucked in them.

[mlroseplant]

Haha, I was faced with that very same thought today while buying my very first pair of heeled boots. I tried on 3 different pairs of knee high boots thinking that I'd really like to wear them on the outside of jeans, but then thinking, "Nah, I ain't ready for that yet." I really love that look on women, though. I ultimately wound up purchasing ankle boots. I am very happy with my purchase.

[Curt]

I like ankle boots too, because my legs are too damn skinny to wear knee boots over jeans. I might look like kate moss at her skinniest! My next thing to do is to wear pumps with the heels totally exposed.

[freestyle75]

Hi Puffer,

first: thanks for the commendation! :-)

I like many of your boots, although not really keen on those with significant platforms. The Costume National boots (above) look great - how high are the heels/platforms, please? I've never heard of them and imagine they are quite expensive.

Funny... if I could only keep two pairs of boots and had to throw away everything else, I would keep the Costume National ones that you chose + the Jil Sander wedges.

To answer your question:

The heel is approx. 5 inches, the platform about an inch.

Costume National is an Italian brand, which literally means "national costume/dress" if translated directly. It was founded in 1986 and operates several clothing brands: Costume National, Costume National Homme (for men, really nice suits!), and C'N'C Costume national (added later, a cheaper, "younger" brand). They operate stores in Milano, Rome, Paris, New York, Fukuoka, Hong Kong and Tokio. Online you can find them either directly via their website (they have an online shop), or via Yoox.com (sometimes) and Saks.com (I've ordered the 2012 boots from there, the reviewer "Carpe Diem" is me, Fashionista was already taken). As you can see, if you are lucky, you can get them at a huge discount (from 760 USD down to 320 USD). I got the boots pictured above at 50% off for approx. 410 USD (310 Euro).

Interestingly, the Custome National high heel boots above run a little large (they are a 41, but feel like a 41 1/2), while this year's Costume National Boots run a little small (again 41, but a little tight at the instep). Nonetheless, I would always recommend this brand - the footwear is actually produced in Fossò near Venice, not in China :-)

Oh... btw... here's my latest addition:

A.F. Vandevorst (I already got two pairs with a lower heel from them)

This was a pair that I bought when I was feeling down:

I had seen a girl in the office with blue skinny jeans and dark brown boots and wanted to create the same look. I knew that the AF Vandevorst boots that I already had in light brown and black would be available in dark brown as well. So I wrote to the boutique in Belgium where I had bought the first two pairs and asked them when these would go on sale. The store answered back that this style never goes onto sale, so I could also order them right away. I placed my order at 3:15 p.m., and got an email 15 minutes later that the store had just sold the last pair in MY size in dark brown color at 3 p.m.

I was really sad that they had sold the last pair. I looked around in their online store and spotted the pair above, which I also liked, but which was too expensive for my taste. I thought to myself "I am going to buy you at some time in the future, but not at this price". Still looking for the brown boots, I searched the online shopping search engines polyvore.com and farfetch.com, and found the boots above at 30% off. Ordered them right away.

So... in the end I still don't have what I wanted initially, but found another pair that I liked very much... they still need to get protective Vibram soles on though, and my cobbler is on vacation till the 7th of January... :-(

Because of the heel and them being knee-high, I am not sure yet whether I am going to wear them outside of jeans or whether I first start wearing them under my jeans. They are the first knee-high boots that have such a high heel.

[Puffer]

Many thanks, freestyle75. Yes, I do like those boots a lot but I could not possibly justify paying 300+ euros for these or anything else, even if they were available in my size (Eu45/46). Oh well ... Your pictures are exceptionally clear. I'm no photographer but (having just got a digital camera for Christmas) am wondering how you get such a good result with highlights and contrast. My amateur efforts will, I hope, grace these pages in due course.

[Jens]

The last two months have seen me evolving from a closet heeler to wearing them in public, thanks to a line of wedges and block heels I found at Buffalo's. My favorite boots have a 14 cm (5.6") block heel with a 3 cm (2.2") platform. They're very comfortable, even for long walks. Only extremely uneven ground is a problem. And well, nobody's even given a look at them... I plan on wearing them all the time except to work (not yet!). Even after such a short time it's come to the point that heels feel more comfortable than flats... well part of it may be psychological No idea where this is going to lead, probably not to stiletto heels in public. Freestyle75, I absolutely love your style, especially the Costume National boots!