Advice for "1st Timers"

[Gige]

This post is a spin-off of comments made on another thread that I thought might make a good topic of discussion on its own. As I did not want this to get buried somewhere very far down on the thread for which it was intended, I decided to just create a new topic. 

I have been giving much thought to the idea of what advice I/we could offer to any man who wants to venture out in public while wearing heels but lacks the confidence to do so. Almost all of the advice I have read here has been solid and offers a great step-by-step guide on how to do so. As far as I know, no one has giving advice to a “first-timer” along the lines of “Get the highest stilettos and shortest leather skirt you can find, go to a biker bar…” I agree that starting small and gradually working towards bigger steps as one becomes more confident is an excellent strategy. The term that has been often mentioned is “confidence,” and I agree that such is essential to a man wearing heels in public. The term “confidence,” however, may have a different meaning to everyone and thus, how such is defined may be open for some degree of debate. I would not disagree with the notion that having confidence is of critical importance, but I recognize that how long it takes for any of us to reach the point of where such exists is dependent on the individual. 

That which has recently dawned upon me is that there are certain facts/truths that any man who wants to (or actually does wear) heels out in public has to accept.  I would argue that in order to build confidence, one must be seen in heels while in public but yet, being seen in heels while out in public is that which we fear. This fear, in turn, prevents an individual from heading out in a pair of heels, which, in turn, prevents the building of confidence needed to overcome the fear of heading out in public while wearing a pair of heels. As just over-explained here, this can be a vicious circle and breaking it may be easy for some, take bit of time for others (like me) or cannot be broken by the rest. I think the key to breaking this cycle begins with the recognition no matter where “we” go, what “we” do, or how hard “we” try to cover our heels, someone will always notice what we are wearing on our feet. Accepting this reality/fact is, as I see it, truly the first step to heading out in public in a pair of heels. If one accepts the fact that they WILL been seen in heels by someone somewhere, and such is the key to building confidence, then “the rest” will eventually come. In time, being seen in heels in public will not be an issue to the wear of such to the point where one may wear heels that other forms of footwear. There have been instances where I have been out in public while wearing heels that have been 90% covered by long pants/jeans and yet, someone notices by directing a compliment to me on what I am wearing. Given what I have learned, I do not know if I would have handled those “early days” differently. Speaking from my own experience, however, now, there is nothing more exhilarating and a confidence builder than being  seen in a pair of heels, regardless of if the heels are fully exposed or not.  It speaks so much of confidence to go out in public to do one’s whatever, and not give a single care to who sees me or what they think about what I am wearing.

[Shyheels]

It’s quite a juggling act. Confidence comes with experience - but getting that experience requires an initial dose of confidence. Finding that is the hard part. And yes people will notice that you are in heels, or tall boots, or both, but not all will notice. A surprising percentage ent notice a thing. And if those who do notice few will have anything to say.

Stilettos will obviously carry more connotations than chunky heels which can, to a degree, be ambiguous.

It will also help if you are open enough to establish what is your natural style in heels and go with that. Positive feelings will build confidence. Don’t turn wearing heels into a numbers game - the higher and more precarious the better. Remember it is a fashion choice - so choose what you like and want without reference to anyone else. 

[pebblesf]

First may I say that Gige's quick progression amazes me, he has accomplished more in about a year than I have in ten years.  And, like you both have said, making progress is a "vicious cycle" indeed.  My Mom used to tell me:  "you are your own worst enemy...."  I think many of us are under the impression (false one) that the rest of the world is waiting outside our door for us to venture out in heels so they can point, laugh, criticize.  While it is true people will notice, but no where to the extent we fear they will.  Most are too busy to notice our footwear.  And for the most part, those that notice will say nothing (another double edge sword for me anyway).  I guess we make the false assumption that most others will notice our heels quickly only because we notice the shoes others are wearing.  

On the other hand, stumbling around in tall heels we can't handle will get us noticed.  As Cali put it, you "have to read the room".   Venturing out in a short skirt and fishnets will probably get you noticed also.  Having negative experiences like this can be a big set back.  This is why it is best to start with heels that are somewhat modest.  We are nervous enough venturing out in the beginning, so this just increases the chances of stumbling or tripping, which why it is important to start out in heels that are not hard to walk in.  Once comfortable/confident walking in modest heels publicly, then we can start to increase heel size and consider some slimmer heels.  

The only other idea I have is to venture out with a girl or guy pal that is supportive.  "Confidence in numbers".   I'm always looking for "heel buds" to hang out with.  I would be lying if I claimed I never get nervous when out in public these days, but it is infrequent for sure.  

[mlroseplant]

At this point in my heeling career, I have a more subtle struggle when it comes to confidence. Now that it is winter, I basically don't have any confidence issues at all. Long pants and heavy coats cover up a multitude of sins. In the summer, however, short shorts and open toed mules expose your every fault. I went through a period a decade ago when I never wore shorts at all, because I felt I would get too much attention. I can't really blame myself, because I think even a cis-woman wearing shorts and very high heels would attract attention, perhaps unwanted.

To address Pebbles's point, I did a lot of walking during those first years in what we would consider modest heels. I don't think I necessarily went about it in a very efficient way, because I think I still looked awkward, having no coach or advisor to say, "You look like a clown*." What it did, though, is allowed me to find my feet, literally, and learn how to navigate the real world in heels without fear of actually falling down. I never would have thought, for instance, that stopping at a crosswalk after walking at a pretty good clip for several minutes, would be hard. Maybe it isn't for some people, but I found that coming to a sudden stop after walking was difficult to do gracefully, as I was struggling to keep my balance standing perfectly still.

* Come to think of it my wife did, but was unwilling to offer any constructive criticism.

[Shyheels]

Undoubtedly having some supportive and, better still a high heel aficionado who can offer useful tips, hints and critique as well as enthusiasm would be wonderful. And a bit of a unicorn, I’m afraid.

My heels, the ones I wear regularly, tend to be modest ones - 3 to 3.5 inch chunky heels in ankle, knee and OTK boots. I’m not so concerned about my ability to walk well in them, at that height and chunky heels to boot, it’s not hard, but would welcome fashion advice about what to wear with my boots - what style/shade of jeans, or style/colour of jumper, coat or shirt, with which pair of boots. I’m never confident of being well put together - and there is virtually no fashion advice columns for men who aspire to wear tall feminine-style boots 

[CAT]

Nervous and fear 12-15 years ago. 
Now, I don’t give a f**k

I can count on 1 hand how many negative comments I have heard in all my years.  
to Pebblesf point, other people are so wrapped up in there phones and staring straight ahead they don’t even notice.  When someone makes eye contact DO NOT LOOK AWAY OR DOWN. Look straight back at them with a nod or a hello.  I have engaged in heel and or outfit conversations as well as conversations that have nothing to do with the heels skirt or dress I am wearing.  I will say from experience that 6” stilettos fishnets and a leather miniskirt will get you noticed and it certainly has gotten me noticed.   I am headed to the Tampa airport and back to Chicago in about an hour and I am wearing a brown sweater dress and patchwork/color block brown and black stiletto knee high boots.  you only live once and I waited to late in life to dress the way I always wanted to.   I’m not hear for a long time I’m hear for a good time 
 

 

[pebblesf]

9 minutes ago, CAT said:

Nervous and fear 12-15 years ago. 
Now, I don’t give a f**k

I can count on 1 hand how many negative comments I have heard in all my years.  
to Pebblesf point, other people are so wrapped up in there phones and staring straight ahead they don’t even notice.  When someone makes eye contact DO NOT LOOK AWAY OR DOWN. Look straight back at them with a nod or a hello.  I have engaged in heel and or outfit conversations as well as conversations that have nothing to do with the heels skirt or dress I am wearing.  I will say from experience that 6” stilettos fishnets and a leather miniskirt will get you noticed and it certainly has gotten me noticed.   I am headed to the Tampa airport and back to Chicago in about an hour and I am wearing a brown sweater dress and patchwork/color block brown and black stiletto knee high boots.  you only live once and I waited to late in life to dress the way I always wanted to.   I’m not hear for a long time I’m hear for a good time 
 

 

Great advice for sure:  never shy away from others when they look at you.  No matter what, "never let them see you sweat".   I am so happy to be close to the "I don't give a f@@k" stage also.  Keep in mind that the men and women that might criticize the loudest are usually the most frustrated because they don't have the guts or build to pull off great outfits like CAT does.  CAT has gone to great lengths to take good care of himself, and grooms appropriately, so definitely deserves all the enjoyment of wearing those outfits publicly....

3 hours ago, mlroseplant said:

At this point in my heeling career, I have a more subtle struggle when it comes to confidence. Now that it is winter, I basically don't have any confidence issues at all. Long pants and heavy coats cover up a multitude of sins. In the summer, however, short shorts and open toed mules expose your every fault. I went through a period a decade ago when I never wore shorts at all, because I felt I would get too much attention. I can't really blame myself, because I think even a cis-woman wearing shorts and very high heels would attract attention, perhaps unwanted.

To address Pebbles's point, I did a lot of walking during those first years in what we would consider modest heels. I don't think I necessarily went about it in a very efficient way, because I think I still looked awkward, having no coach or advisor to say, "You look like a clown*." What it did, though, is allowed me to find my feet, literally, and learn how to navigate the real world in heels without fear of actually falling down. I never would have thought, for instance, that stopping at a crosswalk after walking at a pretty good clip for several minutes, would be hard. Maybe it isn't for some people, but I found that coming to a sudden stop after walking was difficult to do gracefully, as I was struggling to keep my balance standing perfectly still.

* Come to think of it my wife did, but was unwilling to offer any constructive criticism.

I hear ya for sure brother!  I too wish that someone would offer me constructive criticism about the way I walk/carry myself in boots, but perhaps I don't want to know.  Perhaps a video, so I could judge myself.  Better yet, go to some sort of training course for walking in heels!   I do know my limits though.  I have chicken legs, so probably can not pull off hose or tights very well.  But, I do like the way I look in snug levis/some womens' jeans with my boots.  Just a plain older guy in great boots and jeans I guess.  

I was thrilled the other day while wearing my new "Hunter gloss black tall refined rain boots" over my levis while in the mall.  A somewhat younger man who was running one of the concessions went out of his way to come out of his concession to compliment my Hunters and tell me I looked great.   I thanked him profusely.  

[Shyheels]

1 hour ago, CAT said:

Nervous and fear 12-15 years ago. 
Now, I don’t give a f**k

I can count on 1 hand how many negative comments I have heard in all my years.  
to Pebblesf point, other people are so wrapped up in there phones and staring straight ahead they don’t even notice.  When someone makes eye contact DO NOT LOOK AWAY OR DOWN. Look straight back at them with a nod or a hello.  I have engaged in heel and or outfit conversations as well as conversations that have nothing to do with the heels skirt or dress I am wearing.  I will say from experience that 6” stilettos fishnets and a leather miniskirt will get you noticed and it certainly has gotten me noticed.   I am headed to the Tampa airport and back to Chicago in about an hour and I am wearing a brown sweater dress and patchwork/color block brown and black stiletto knee high boots.  you only live once and I waited to late in life to dress the way I always wanted to.   I’m not hear for a long time I’m hear for a good time 
 

 

Yes you do a very good job of putting things together. With my ensemble of boots, jeans and jumper there is little room for your style of creativity. I could never do the leather miniskirt - although I admit that the other day I noticed an ad for a leather midi pencil skirt, calf length, that did pique my interest, something I could at least imagine with my OTK black suede boots

[Cali]

I remember over a decade ago when I switched to only women's shoes and got my first booties with 2 inch heels. The hardest thing was getting use to the click.

BUT

I'm in the too "old-to-care" group, buy and wear what I want. I just got a cheetah vest, so soft, and already wore it to a company holiday party with my 3.5 inch thin-heeled knee highs. Both the vest and heels got random compliments. I also like wearing short-shorts and sitettos knee highs in the summer, just for the mind blowing effects of it.

 

5 minutes ago, Shyheels said:

Yes you do a very good job of putting things together. With my ensemble of boots, jeans and jumper there is little room for your style of creativity. I could never do the leather miniskirt - although I admit that the other day I noticed an ad for a leather midi pencil skirt, calf length, that did pique my interest, something I could at least imagine with my OTK black suede boots

I like my pleather skirt with knee highs. LOL

[bluejay]

Shyheels, I have a fauxe leather mini skirt, and I do wear it with fishnet hose, with pumps in the warmer months and knee boots in the  colder months. I have gotten a few compliments wearing those ensembles. I like to dress and wear what I like, with leather and fishnets, those are favorites of mine!!!!!!

Happy Heeling,

bluejay

[mlroseplant]

We have some weather in my locale, I was supposed to work today (yes, on Saturday), but the whole job is shut down. I needed to move my car off of the street, and I slipped into the heels that were closest, walked outside, and nearly fell on my backside. Freezing rain is so much fun! Walked back inside, got my flat boots to move my car, and still am fortunate to have remained upright. Advice to first timers: Do not walk on ice in heels. In fact, do not walk on ice unless it's absolutely necessary!

[Gige]

1 hour ago, mlroseplant said:

We have some weather in my locale, I was supposed to work today (yes, on Saturday), but the whole job is shut down. I needed to move my car off of the street, and I slipped into the heels that were closest, walked outside, and nearly fell on my backside. Freezing rain is so much fun! Walked back inside, got my flat boots to move my car, and still am fortunate to have remained upright. Advice to first timers: Do not walk on ice in heels. In fact, do not walk on ice unless it's absolutely necessary!

Oh, I see you get to have all the "fun" weather! 🥶

[Shyheels]

I wore my chunky heeled ankle boots (3.5” heels) for a half miles walk down the towpath yesterday to get rid of some rubbish. It wasn’t muddy just uneven and I had to walk carefully. I was certainly noticed, and fair enough - nobody wears heels on the towpath.