My first proper outing but....

[Pointer7]

.... I wore flats, opaque nylons and black jogging bottoms... All black so no one noticed so not really heels!

it felt really good, it was late at night and I was still a bit nervous but the longer I was out the more I didnt care, I had to walk to get my car so thought what the heck lets try it! It was an hour long walk and I'd only ever walked around my estate before but this was through the city centre so I'm happy

Maybe try a supermarket late at night next! 

 

[Steve63130]

It gets easier every time. The demons are in our heads. Most people don't notice and those who do, don't care. Teenage girls in a group will giggle. That's mostly it.

Steve

[SF]

Flats are no big deal, I have worn gals flats since I was a teen and that (unfortunately) was a long time ago.  Try some heels, you won't regret it.  Like Mr Steve says, it does get easier every time...   Have fun...  sf

[mlroseplant]

3 hours ago, Steve63130 said:

It gets easier every time. The demons are in our heads. Most people don't notice and those who do, don't care. Teenage girls in a group will giggle. That's mostly it.

Steve

[mlroseplant]

Teenaged girls in groups may giggle, teenaged boys in groups may heckle. Teenaged girls individually will tell you you're really cool, and might even ask for advice.

Old ladies may eye you with suspicion at first, but then later tell you that they used to rock high heels in their younger days. They secretly admire you. Old men? They just think you're odd, and either accept you, or they don't. This has been my experience.

I have my shy moments, don't get me wrong, but usually I can wear my heels every day with pride, and I have guys like Steve and SF to thank for that. Good luck!

[ShockQueen]

The main thing, and I'm sure others have said this, is confidence.  If you wear your shoes like nothing new and just go about like nothing is out of the ordinary, less people will notice.  If you act and walk nervous, then it draws attention to your feet, and can defeat the purpose.  Walk with a smile and your head held high!  Go for it!

[Pumps]

6 hours ago, Steve63130 said:

It gets easier every time. The demons are in our heads. Most people don't notice and those who do, don't care. Teenage girls in a group will giggle. That's mostly it.

Steve

No sure I agree with that. People notice and people care, but very few of them will do it to your face and rarely you a hard time. I wear both pumps and boots a lot and while people DO notice, I rarely get any response. I think most people think it's a bit embarrasing, that a man would go around in heels, so you need to not care what people think and that's easier said than done.

[Pointer7]

That all makes sense... I was gradually walking a bit more relaxed and not worrying about walking past people and who knows maybe one day I might try a small heel! Thanks for all the replies 

[Thighbootguy]

3 minutes ago, Pointer7 said:

. I was gradually walking a bit more relaxed and not worrying about walking past people

Don't worry  about people noticing your wearing heels especially boot worn over jeans... THEY DO NOTICE...they just don't care. If you're spending all your time worrying about being seen wearing heels, stay home.  If you are constantly worried about hiding your heels when your walking, you won't enjoy yourself at all and a heeled outing won't be any fun. The worry is all in your head (really) and people really don't care what you have on your feet. 

This advice assumes that you are not one of those people that exists just to have something to worry about and if you weren't worried about being seen in heels you would find something else to worry about.

Life is short... Enjoy your heels.

[pebblesf]

Great work buddy!  You are doing it right by starting off slowly, wear your flats to the food store or mall for some short outings, increasing your time out each time.  It won't be long before you forget about the shoes you are wearing, then you can gradually move on to higher heels.  Try not to concentrate on possible reactions, trust me I know this is much easier said then done. Remember confidence is key, "never let em see you sweat".  Most guys have a secret desire to wear heels, they just don't have your courage!

[Histiletto]

I'm sorry that the social programming has caused so many guys to think wearing what they have come to like is detrimental or at least hurtful to the others they may cause to notice. Females, by social decree are suppose to be the weaker sex, but they seem to be able to wear whatever they like with out any notion they are harming others (which they aren't). So why are men so afraid of being seen doing what they want to do? Are they afraid of hurting the ones that say they love them. Wouldn't those same people be happier knowing their loved ones are happy with who they are, rather than learning later it was all an act just to win their favor. When are men going to learn how to be responsible for who they are and not what others tell what and how to be? If we have to put on a show to be accepted by those who say they love us, what do they have love for? Your compliance with their expectation. Unconditional love is a foreign concept to most people, because we have been taught love has to do with letting others control us. Parents have the responsibility to show and teach their children how to enjoy/deal with living and make the best of their lives by choosing the right paths. Once the children are mature enough to make their own decisions, that part of the parent's obligation is complete. However, society continues trying to make our personal decisions for us. This has never been part of the stewardship of society. They don't and can't know the feelings and desires of every individual. The way things have been set up is like a "one size fits all" kind of thing. Each person has their own set of talents and tastes, which means there are so many different personalities, one size can't fit more than the groups of people that are satisfied to let others run their lives and that are scared when others seem to disrupt the way things are by following unauthorized or uncondoned paths or stereotypes. As for men wearing footwear labeled for women, this is one of the ways society has created to control what they consider appropriate, which can be changed when enough men wear their choice of heels openly and regularly. The market wouldn't be able to grow fast enough for the immediate demand.         

[HappyinHeels]

Pointer7,

All great advice you have received here. Whether it's the flats you are wearing today or the pumps you will be wearing tomorrow they should be worn and celebrated with the confidence that comes when you make the world meet you on your terms. Reread what HiStiletto says about society making choices for us. Now imagine that for a moment: nameless and random strangers making choices for you... a free person. Adults making your decisions for you ostensibly ended once you reached the age of maturity yet many men allow their fashion choices to be made by people that have no vested interest in them. When it is analyzed very closely it is a pair of shoes. By themselves they do not convey a political statement, nor a declaration sexual preference, or even a statement of availability. Unless you want them to. That's the human touch. The touch is mastered when it is expressed with the confidence that keeps your head high, your heels in stride, and your eyes level as you greet the world on YOUR terms. Keep this in mind and you'll be a natural in no time at all. HappyinHeels 

[Histiletto]

It is really frustrating to realize that we, as men and even women, have been taught to fear the wrath of society should we wear items we find pleasing to our tastes that others wouldn't necessarily choose for us. Does anybody see this is another way of causing people to live under the conditions of servitude, enslavement, and/or bullying to others? The other day I watched "A Bug's Life from Walt Disney DVD. It showed how a larger population of ants were being terrorized by a group of grasshoppers. As long as the ant were scared and stored an amount of winter food for the terrorist, the ants wouldn't have to fear being harmed. However, the grasshoppers knew that if the ants began to not fear them and didn't supply their winter storage, there weren't enough grasshoppers to overpower the number of ants. So, it is with us as people. Society has ingrained a fear in us to follow its bidding on matter that it really has no jurisdiction. Namely, our personal agency to make our own decisions according to the tastes, interests, and perspectives that comes from who we are as individuals. Just because others don't want me to wear stileto heels, doesn't mean my desire to is less valid or important to be fulfilled. They probably have some desires that I wouldn't go for, but that doesn't mean I can or should stop them either. Trying to take away any part of one's personal agency goes against the natural order of things and causes that individual to be less open to receiving or giving depending on the circumstance. When we feel such restrictions, the unfulfillment tends to occupy a part of our thought process with means we my not be able to give a full measure of attention or concern to the all matters before us. Many a youthful or mature dream/desire have been stifled into secrecy or dwindled away because of societal influences, only to later revive as an obsession. Could this be a part of the reason mental health problems have become more exposed in peoples lives as they grow older?

[Drew80]

I think the human brain is made to accept only a few reality at a time. What we find normal now might be considered stupid later and what is stupid now might be normal. It is also normal to seek for people with the same value as us, this is why "society" work as the value of the mass is therofore used. In some way we created a small society here to seek acceptance. I dont think no one but us is stopping us from wearing heels right now. I do am afraid of social judgement, but each time we go outside we get judge from what we wear, what we say, what we do. We / I decided to put more importance on the judgement made on the fact that I wear heels more than the other. Never forget that less than 20 years ago we were harrassing the gay people for no reason because that was the norm.

[Drew80]

And some people are just simple stupid and stubborn. Some still think the earth is flat, that the woman place is in the kitchen only, that gay is a disease and so many more stupid shit.