Man On High Heels

I don’t know why, but there is something about a man wearing high heels that really ticks me. And if his heels are on a pair of thigh high boots then I’m sold!

I have a very good female friend who has this story to tell:

“Luckily I have a boyfriend who likes to wear both tall boots and high heels. He does so both in private and in public, but it hasn’t always been like that. At first he only wore his high heels indoors in private. And it took quite a long time before he dared taking his first steps outside.

Man wearing high heeled thigh high boots

It is sad but it seems true; what we fear the most is how those closest to us will react. Friends and family, neighbours and community. The first time he put on a pair of high heels was when we had a vacation abroad. It was a pair of booties with 8 cm. (a little more than 3 inches), block heels safely tucked away under a pair of long legged pants. I think the sound alone when his heels hit the ground scared him. But guess what – nobody raised an eyebrow. And I believe the keyword here was confidence. He tried his best to appear confident when walking.

Why am I telling you this story? I’m doing it because I believe there are men out there who would love to wear their high heels out in public. And hopefully this article can encourage some of you to take your first steps out the front door.

When we got home, I was afraid that he would pack away his heels, (or tall boots), and go back to only wearing them around the house. So we had a talk about it, and he continued wearing high heels. At first when driving back and forth to work, including stopping for gasoline.
Also, I would insist that he wore high heels when we went shopping for groceries. At first we chose malls that were at a distance from where we lived, and gradually worked our way closer to home. By now the keywords were; confidence and natural. By wearing high heels as often as possible it became a more natural feeling for him when walking down the street or into a mall in his high heels.

Man wearing high heeled thigh high boots

Today, putting on a pair of high heeled boots is as natural to him as putting on a pair of sneakers. Now it is more a questing about which pair of boots matches the outfit best.

Of course there are also times where high heels isn’t an option for him. For instance at work related activities, because of the office dress code and also for not wanting to put clients in an awkward position. We both know that not all people are comfortable with seeing a man wearing high heels and try to respect that in some circumstances. And there are also some parts of town that it simply wouldn’t be wise for a man to walk around in high heels. I know – that is so sad. But I believe the only thing that helps is if more men start wearing high heels in public and not make a fuzz about it.”

For those of you that landed on this article and who are not used to seeing a man wearing high heeled thigh high boots – I have a request:
Don’t judge, harass or jump to conclusions. Be open minded and let people wear whatever they want. After all – it’s a pair of very nice looking thigh high boots. Luckily for me, it’s my friends boyfriend who are wearing them!

10 Comments
  1. Well, I think he nailed it. This is what I would say as, being comfortable in your own skin. I, myself, have worn high heeled boots, but only in the house. I do, however, wear 3, maybe 4 inch heels in public. As I wear mainly over the knee boots, and higher, my wife is always on the lookout for stares. I’ve gotten to the point where I just don’t care anymore. The one thing that annoys her, though, is when someone tries to snap a photo. Ah well, such is life. Rock on.

  2. Hi I loved your comments regarding men wearing stiletto boots.I have tried on knee high boots with a five inch stiletto heel..black is my favourite colour. But for a long time now I’ve always wanted to try a pair of otk boots myself but not had the courage to go and purchase some. Preferably a platform design so they have a tall stiletto is my favourite. Your guy is lucky to have a partner which is very open and ok with a man to wear what makes him happy.

  3. I am 60 yrs old, but very slim and now live in Southern Spain and the Spanish are a lot more tolerant with what a person is wearing than the English. Over here I wear OTK leather boots with a 3″ block heels on the outside of my tight skinny jeans and nobody bothers. You should wear what you want and not what other people think you should wear. I love not following the “norm”. I am sure a lot of women find a man in high boots appealing.

  4. Wear you boots and heels with confidence and pride. You only live once, and you should not be going through life restricted by others opinion on what you wear on your feet.

    1. Rock on indeed & wear whatever feels right.

      I wouldn’t go for “heels” myself but I’d like some “ordinary” knee-high boots … if there were just any available in my size. For now, my Dublin River boots have to do.

      The LTS Roxi biker boot from “longtallsally.com” came close. Warm winter lining, very nice. I’m just not too keen on the metal “bling” … if they’d been plain black I would probably have bought a pair already. 😉

      I sense a change in the air though. Think we will see mainstream knee boots for guys within the next five years or so.

    1. You might be right about that. Having a supporting partner is probably a good help. But at the same time – It’s just footwear. Even though I consider myself a boot fetishist, I can’t understand why people can’t dress the way they want without getting odd looks or comments. If you are a guy and want to wear a dress or skirt, then you should do so. (Or at least feel that you are free to do so!).

      1. I do own a few pair of leather knee high boots with 3 cm heels. As to the support of a partner, I have experienced both extremes.

  5. Let me see. Where do I start. Well, Isabella, and I thought I was the only one with a boot fetish. At least, one that would admit it. And, yes, why do people get all winky about it. It IS only boots for goodness sake. Although…How about posting more pictures of men sporting their outfits, or soliciting requests? What thinketh the dames? Would they enjoy it? It has occurred to me that it is going to take the older gents, you know, the ones that are comfortable in their own skin, to show the way for the young dudes and dudettes. What thinketh ye,all? Hm?

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