What age did you seriously start wearing heels?

[VirginHeels]

Just a question that has popped into my brain recently. What age did you seriously start to wear heels? I’m not just talking about the once or twice a year thing. I’m talking about seriously on a daily or weekly basis?

Id love to do so, however my job and lack of a social life prevents me.

Thanks in advance.

[Shyheels]

Well, let's just say I waited a long time - too long - to buy my first pair of heels. I was well into middle age before I dared to give it a try - even just wearing them at home. I felt guilty about wanting to try wearing high heels; I mean, what if I liked it? 

You mention job and social life as the things that are holding you back. But you don't need to wear them out and about if it makes you feel uncomfortable. Sure, quite a few of the guys on here do  - and cut quite a dash. But it doesn't mean you have to. You can buy yourself a pair of heels tomorrow and wear them to your heart's content at home or in private or in whatever way or place works best for you. It's not a contest to see who can push the envelope the farthest.

As for me I own a couple pairs of stiletto boots, but I don't wear them out and about, but instead at home while I am working. I do this in part because I am not well practiced in wearing them, in part because of where and how I live they would only get ruined, and partly because my natural style runs to knee and OTK boots with chunky heels, rather than stilettos. I bought some stilettos because they are the Ultima Thule of heels and (for guys) taboo breaking and I like wearing them, but when I am getting dressed the chunky heeled boots call out to me more often (which is why I am not well practiced in stilettos)  I sm comfortable wearing feminine knee of OTK boots (with and without heels) out and about, but that's me.

The point is it is not a competition. Wearing heels it doesn't need to be about towering stilettos or cutting a dash in public. It's about freedom of choice and your own personal style. The world doesn't make it easy for a guy to wear heels, but you don't have to wear them in public if you don't want to. Wear them at home. It's better to do that than never to try at all.      

 

 

[Cali]

I acquisitioned my first wife’s shooties (shoe-bootie) one day in the late 70’s because my dress shoes didn’t look good with the suit I had on. I was in my early 20’s. They became my dress shoes until I wore them out in the late 90’s. Great leather shoes with a 2.5 inch heel. Then in about 2008 I needed water shoes for a trip to Hawaii. They ran out of men’s in my size. So, I tried the women’s size 10 and the men’s size 10. To my surprise the women’s size ten fit better than the men’s size 10. 

In 2011, I researched shoes that fit my feet and it turned out to be women’s. Haven't bought a pair of men's shoes since then. I started with 1.5 to 2.5 inch booties. Today I only wear women’s shoes. Mostly 4 inch heels everywhere including board meetings.

[mlroseplant]

Although I've had a fascination with heels since childhood, I did not actually start wearing heels for real until age 44, in 2012. I started with clogs before that, but the first time I wore shoes with an obviously elevated heel was in May of 2012. They were also clogs, but with about a three inch heel. I stuck with clogs for quite a long time before I tried some other styles, and today I will wear just about anything that I find attractive.

[pebblesf]

I would say that my "fascination" with boots and heels began when I was just a little kid.  I have often wondered if this "fascination" is something I learned, or was I hardwired this way.  Unfortunately, I waited until my late 40s-50s to actually allow myself to admit that I wanted to wear high heel boots and get some....  It has taken me many years since then to develop the courage and confidence to wear them in most any setting these days without the usual self imposed negative feelings.    Thanks to all my friends here for your help.  Don

[Shyheels]

2 hours ago, pebblesf said:

I would say that my "fascination" with boots and heels began when I was just a little kid.  I have often wondered if this "fascination" is something I learned, or was I hardwired this way.  Unfortunately, I waited until my late 40s-50s to actually allow myself to admit that I wanted to wear high heel boots and get some....  It has taken me many years since then to develop the courage and confidence to wear them in most any setting these days without the usual self imposed negative feelings.    Thanks to all my friends here for your help.  Don

Like you, my desire to wear boots goes back to childhood - in my case fancying a pair of white go-go boots like this girl in my seventh grade class wore to school about three days a week. And resenting the fact that for me they were forbidden. I don’t remember if they had heels or not - most go-go boots didn’t, I don’t think. I just remember liking the hippie-chic styling and wishing I could wear those too.

How and when heels came into the equation, I’m not sure. Even now they are not the be all and end all, but rather a jaunty touch to knee and OTK boots. It’s the overall effect I like, not just the heel.

[Chorlini]

For me it started in the 90's. If only because my feet were just too big for what was available in retail in the 80's. And when I gained the ability to live and more importantly travel by myself as a student in the 90's (we got free public transport as students in the Netherlands back then) I was finally able to go to fetish shops in Amsterdam that had shoes in sizes bigger then EU41. They were also all 12 to 14cm high, but what did I know at the time, so that was what I got used too with practice.

[Gige]

I think trying to define "seriously" is, for me, somewhat tricky. For most of my life, I wore heels "in secret" and thus, did so only when the opportunity presented itself. I would not do so if it was only for 30 minutes or an hour because it was not worth the effort. So, my wearing of heels was sporadic and the frequency of such varied. During this time period, I would only wear heels indoors and venturing out was under the cover darkness late in the evening. Fast forward to November 2023 when I started wearing heels in public. Now, the situation is reversed - I mostly wear heels out in public and will only do so at home during my work day.  So, I guess it might be fair to say that for me, it has been since the aforementioned date that I have been "serious" about wearing heels although I have always done so. It is worth noting that my wearing heels "in secret" was not as developed as it is now for obvious reasons. By developed, I mean that in the sense of having a wide variety of choices and matching outfits. 

18 hours ago, Chorlini said:

For me it started in the 90's. If only because my feet were just too big for what was available in retail in the 80's. And when I gained the ability to live and more importantly travel by myself as a student in the 90's (we got free public transport as students in the Netherlands back then) I was finally able to go to fetish shops in Amsterdam that had shoes in sizes bigger then EU41. They were also all 12 to 14cm high, but what did I know at the time, so that was what I got used too with practice.

Do you shop at Shoebidoo in Utrecht? I have bought several pairs from them but delivery is expensive. I would love nothing more than to arrive at Schiphol, get out my OV-Chipkaart, and get on the NS out there. 

On 9/4/2024 at 10:59 AM, pebblesf said:

I would say that my "fascination" with boots and heels began when I was just a little kid.  I have often wondered if this "fascination" is something I learned, or was I hardwired this way.  Unfortunately, I waited until my late 40s-50s to actually allow myself to admit that I wanted to wear high heel boots and get some....  It has taken me many years since then to develop the courage and confidence to wear them in most any setting these days without the usual self imposed negative feelings.    Thanks to all my friends here for your help.  Don

I have come to believe that when it comes to wearing heels in public, we are our worst enemies. It is so easy to think that when "we" step out in public in a pair of heels, the eyes of the world instantly focus on us and what we are wearing. I am sure that every one of us has felt this way - I know I have. In reality, I do not think a vast majority of people notice or care. The "only solution" to this problem is to get out there and do it. In less than a year, I have gone from being incredibly nervous to not giving a (expletive starting with F) what anyone else thinks about it. Always remember the words of Dr. Seuss: "Those who mind don't matter and those who matter don't mind." 

[pebblesf]

1 hour ago, Gige said:

I think trying to define "seriously" is, for me, somewhat tricky. For most of my life, I wore heels "in secret" and thus, did so only when the opportunity presented itself. I would not do so if it was only for 30 minutes or an hour because it was not worth the effort. So, my wearing of heels was sporadic and the frequency of such varied. During this time period, I would only wear heels indoors and venturing out was under the cover darkness late in the evening. Fast forward to November 2023 when I started wearing heels in public. Now, the situation is reversed - I mostly wear heels out in public and will only do so at home during my work day.  So, I guess it might be fair to say that for me, it has been since the aforementioned date that I have been "serious" about wearing heels although I have always done so. It is worth noting that my wearing heels "in secret" was not as developed as it is now for obvious reasons. By developed, I mean that in the sense of having a wide variety of choices and matching outfits. 

Do you shop at Shoebidoo in Utrecht? I have bought several pairs from them but delivery is expensive. I would love nothing more than to arrive at Schiphol, get out my OV-Chipkaart, and get on the NS out there. 

I have come to believe that when it comes to wearing heels in public, we are our worst enemies. It is so easy to think that when "we" step out in public in a pair of heels, the eyes of the world instantly focus on us and what we are wearing. I am sure that every one of us has felt this way - I know I have. In reality, I do not think a vast majority of people notice or care. The "only solution" to this problem is to get out there and do it. In less than a year, I have gone from being incredibly nervous to not giving a (expletive starting with F) what anyone else thinks about it. Always remember the words of Dr. Seuss: "Those who mind don't matter and those who matter don't mind." 

Well said