Skip to main content

High Heels for Men

  • Author:
  • Updated date:

High heeled shoes or stilettos are one of the most powerful symbols of feminine fashion. If you men want to explore the sensation of looking like a woman and I think every man should, then finding a pair of high heels is an absolute must.

And you’re living in the right times for it. Mens high heels are becoming more and more available in shoe shops. You no longer have to search through women’s shoe shops looking for something that you might be able to squeeze into. Modern fashion has everything and you can now more easily buy high heels for men in larger sizes. There are online stores that specialize in mens high heels and there are crossdressing shops where you can order high heels for men and transvestite shoes anonymously. So get into those stilettos boys and start feeling like a woman.

Image by Annie Mole at

Image by Annie Mole at

Why high heels for men?

I have a bit of a shoe fetish myself but I think that’s somehow programmed into the female mind at birth. There’s no doubt that high heels look very aesthetic even by themselves. But they also shape the legs and feet into a more graceful position and make the legs look longer overall. So high heels are not really about being taller (although I do really like that part). They’re more about a beautiful silhouette and nicer body proportions. Check out my articles mens tights and mens pantyhose for a nice complement to high heels.

High heels for men are a great way for you to look feminine but they'll also make you feel like a woman. It is much harder to walk in them and you’ll instantly feel less agile and more vulnerable. I love vulnerability in a man. It is such a beautiful thing to see. Perhaps it’s because it’s so rare and secret that makes it so special.

Shoe Sizes

I’m sure you don’t need to be told how important it is to get the right shoe size and fit. The only way to know if a shoe fits is to walk in it for a while. That’s no different with high heels for men. But don’t expect too much. Because high heels are just not known for their comfort even if they fit perfectly (welcome to feminine fashon) and mens high heels wont be any different there.

What you need to watch out for is the difference between men’s and women’s size charts. When shopping for mens high heels, you need to make sure you know which size chart that particular store is using. When ordering online, this isn’t always obvious. Crossdressing stores for example, will probably use men’s sizes for their women’s shoes but other online shops will probably use women’s sizes. When in doubt drop them a message to make sure.

The other trap that you might fall into is the different size charts across different countries. With 21st century internet shopping, it’s quite common to order from an online shop that’s located in another country. For example, UK sizes are nothing like European sizes. But most online stores give you several charts and the option to convert between them.

See also my articles:

Walk in Her Shoes.

Men Wearing High Heels


Joanncd on June 27, 2013:

I wear high heels all the time at home, but only out if I am away from where I live. I have been gifted with great legs (thanks Mum) and my SO has no objections to me dressing up for dinner, provided I take care of the wine requirements.

maggie Detreich on June 25, 2013:

Life is full of amazing exhilarating moments if only we give ourselves permission to open our minds to these new experiences. It's more about attitude then about culture. Changing your culture will seldom change your attitude but changing your attitude will often change the culture that surrounds you.

Michael from Rocky Mountains on June 19, 2013:

Exhilarating is the feeling that swept over me the first time I slipped into a pair of high heels. They were red patent leather with a 3" heel that were quite easy to walk in and felt very comfortable. I tried some higher heels but found them hard to walk in and would need time for my legs to adapt. Since then I've discovered wedges and strappy high heels and now own about 25 pairs of women's shoes. My GF enjoys it when I wear the strappy heels and now insists on painting my toes and wearing sheer toe nylons whether they be pantyhose, thigh highs or stockings with garters. We have gone to the drag bar in high heels many times amd love checking out the clearance shoe racks at Nordstoms, Macys, JCP, sears, etc and of course Payless shoes. I'm hooked on the look and feel of high heels. Michelle

maggie Detreich on December 13, 2012:

"Just curious but are high heels uncomfortable to wear or just walk in and are they all like that and also do all corsets constrict breathing or just some."

I think you just have to be aware of your restrictions in heels and make the necessary adjustments in your walking. They take a lot of getting used to especially if you wear them for long periods of time. I have some pretty comfortable heels with about 2 1/2" heels but still by the end of the day there are times I find myself working in my stocking feet. Personally though I am willing to trade a bit of discomfort for the look and the way they make me feel, bottom line I feel a bit frumpy working in flats. You can be comfortable in sneakers or stylish in heels.

Scroll to Continue

Lucy83 (author) on December 11, 2012:

"Just curious but are high heels uncomfortable to wear or just walk in and are they all like that and also do all corsets constrict breathing or just some."

High heels are always uncomfortable to walk in. Sure some are better than others but they never are as good as flat shoes. I'm not a corset wearer so I'm not an expert but certainly the breathing restriction depends on how tight you bind it.

samowhamo on December 09, 2012:

Just curious but are high heels uncomfortable to wear or just walk in and are they all like that and also do all corsets constrict breathing or just some.

maggie Detreich on October 04, 2012:

My first pair of heels were bought at an Adult Book Store in Las Vegas Nevada. I paid about $30 for them at the time and they had a 6" heel. At the time I only had the courage to wear them around the apartment when noone else was around and they hurt like hell.

I guess at the time I confused femininity with dressing like a hooker. Today I am a bit more practical. My highest heels are about 4" and most of the time I prefer about a 2 to 2 1/2" heel. I am blessed as I work in a beauty salon where my co-workers are a bit more open and supportive then people would be in a lot of businesses and the majority of the time I do wear heels to work. I guess I just figure that if they can live with my long multicolored layered hair they can just learn to accept my heels.

Normally you will find me in ultra tight ankle length jeans, hose, 2 inch heels or so and a black smock, pretty much the attire of most everyone working there and aside from a few compliments on my appearance from a few of the older ladies everyone treats me much the same as they would anyone.

70's cat on April 01, 2012:

I'm a guy, and I wear 70's chunky heels(2-3 inch). It has nothing about being womanish. In the 70's if you want to kick it pimpin' style, that is how we dressed. I might wear wedge heels, but not spiked heels like the women wear, only the ones made for men. And put them with some funky bells.

Blacksheep557 from NewZealand on November 27, 2011:

If the wearer of heels has practiced, and has good flexiblty, there is little reason why one connot walk distances almost as far as when wearing flats. It is important that the shoes fit well. My preference is a heeled hiking boot with a 4 1/4" block heel (about 1" x1") The furthest I have walked with out a break is 8 Kilomtres. wearing flats my legs would also feel tired, so no greater discomfort wearing heels. Generaly I would walk about 4 Kilomtres at a time. I have never over heard any negative comments, and few people even glance to the ground to see my shoes.

There are many ways that men can wear heels, with the trousers covering the whole heel, trousers covering part of the heel , or cuffs turned up about 100mm (4") showing much of the boot or shoe. each to their own and comfort levels in my opinion. thanks ofr te Hub Lucy

robert-hathaway on November 10, 2011:


jd on September 14, 2011:

So much talk about freedom in the USA, and about protecting freedom in other countries. Yet so many people today seem to have a desire to oppress a personal choice freedom. And even those that seem to defend this personal choice seemed to miss the mark. Case and point, while the historical origins of heels and references to women wearing men's clothes such as jeans are justified arguments. They do not expose the truth of what has really been going on over the past 50 years. The real truth is that sexually explicit material "porn" has been shaping the thoughts and ideas of each new generation. In pornographic films dating back to the early 70's, women are filmed wearing high heels while having sex. Magazines offer up photos of women completely exposing themselves yet still wearing those heels. When I was growing up, I really don't remember that many girls or grown women wearing the heels that I saw in pornography. As time moved on and and porn was able to link it self to rock then hip-hop/rap and finally POP music, we have seen the shoes of sex fiction move into fashion. That is why so many guys are quick to say it is homosexual, because of porn they equate high heels with someone getting f**ked by a man, or someone in heels giving a man a b***job. Their physiological programming can't handle the site of a man wearing heels. And the women have had the same brain washing. Women if you want to keep high heels for women only, then you are buying into the use of women as sex objects. A vicious cycle of sex, money and oppression of the freedom of choice.

Royce on August 11, 2011:

Great article Lucy!

@ MaraSophia- High heels were actually first worn by men in the parliament in England as early as the mid 1700's, but like alot of mens clothing women took them over and called them their own.

TimTurner from Phoenix, AZ on April 07, 2011:

I started a blog that features high heels in mens sizes :) It's

I have a friend who wears high heels and he always said it was hard to find sizes lol

Why not? Seems to be a growing niche fo sho!

Rustyrustynail on January 07, 2011:

I was worried about buying a pair of heels. Although I have loved female and in particular nylon underwear for years i had never really thought of shoes. Then I searched on Google and found that I could have shoes delivered to my local shoe shop. But which size? I am 10 1/2, and most seemed to be sold in 10 or 11. I looked on ebay but not much help nor choice there. Then I suddenly decided to search the local charity shops and found a pair that looked about right. I did not dare try them on in the shop. The only cost £1, so there was no risk. As soon as I got home I tried them on and - they were a perfect fit. About 2 1/2 inches, they are not as difficult as I though they would be.

I was really surprised at how feminine they made me feel. And i became conscious of how i placed my feet. It is easy now to see when my feet look gauche and awkward, and easy to move them so that they look "right". Don't know if I shall buy any more, but we shall see!!!!!!

Assassin Fred on January 07, 2011:

Ive never braved the streets enfemme yet, maybe someday. But for most men, add two sizes to your mens shoes size, that you have your female shoe size (for the most part).

Rikkie Lee from Ontario, Canada on December 23, 2010:

If the truth be known Lucy ... the things I do are so very different than the things I'd love to do with respect to presentation and clothes. My wife just won't allow my girl side to be totally visible in public. How I wish it weren't so, but it's fact!

So my public outings are mostly on the sly. An ex-girlfriend told me something that made sense about secrets.

Lucy83 (author) on December 22, 2010:

Now the truth is out Rikkie. You're a seasonal conformist trapped in an awesomely dressed body ;)

I actually don't like noisy heels though I still - and how people often seem to think I'm just trying to attract attention. Well try and walk quietly in them. Still it's a small price to pay.

Rikkie Lee from Ontario, Canada on December 22, 2010:

I love wearing heels in public, even when not dressed completely en femme ... going for more chunky heeled boots than stilettos for stability, comfort and seasonal conformity under boot-cut jeans or dress slacks. Just love the sound in a mall hallway ... mine and somebody elses, who usually would be a woman. I still feel somewhat uncomfortable and self-conscious because of the looks I occasionally get and because very few other males wear heels or heeled boots. The tallest I've worn in public are 4 inches.

Lucy83 (author) on September 20, 2010:

Lol Marasophia. Now there's a great argument for men to wear high heels!

MaraSophia on September 19, 2010:

Adopting an erect position for walking took human kind millions of years of evolutionary process. By walking on tiptoe because of using high heels wouldn´t women be taking a step ahead of men in that evolution process ? Men should start wearing high heels if they don´t want to fall behing women.

Lucy83 (author) on August 15, 2010:


Thanks for the great coment. I love the part with the monkeys. So true!

Histiletto on August 09, 2010:

I appreciate your acknowledgement concerning men wearing heels. The quality and look of heels has improved dramatically since society determined only women should wear them. It seems there is a social phobia about men and women having the same desire to wear the same high heels. However, women can do all the things men can, but men breaking into the realm of "femininity" are looked down upon as though having female taste and tendencies are bad qualities to possess. We've got to correct this attitude and thinking. Both are human beings with all of the same senses and abilities to learn and grow. Wearing high heels, whether stilettoed, blocked, or etc., should be just another choice of footwear for any person. The shoes themselves do not have a preference.

Have you heard what monkeys do when they are forced to stay in a barrel for quite a while. They will keep new monkeys from leaving also. It society's monkeys that continue to stereotype people into certain roles which keeps others from being the people they are.

The unfamiliarity of men wearing high heels causes people to react negatively, because of our social attitude. The same type of reaction happened when women started working out of the home and had to dress in men's clothes to do their job. Now it's commonplace for women to be in what use to be the men's business area. This has been a good development for everyone over all, because women have shown they have the ability to choose their skills in bettering our world. They are free to express themselves in so many way. Their wardrobe is only one of the evidences for their freedom to choose according to who they are.

Having the freedom of choice helps women to be who they are. Why doesn't society let the men that are willing to choose have the versatility of freedom? So they add wearing stiletto heels or other clothing adornments now determined to be for women to their wardrobe. Isn't life for living and not living someone elses determination of life. Happy heeling, people!

Lucy83 (author) on June 12, 2010:

Thanks Schnaubler.

Well it's not my site, I just post articles here. Maybe I'll start my own site some day.

I know the high heels are so not suitable for long walks which I also love to do. It's also not healthy to wear them all the time. I suppose that makes it more special when you do.

schnaubler on June 12, 2010:

Wehell I gotta comment this too...High heels are...a must for me. I do not only feel 'sexed up' wearing some, they also seem to raise my personality. Yeah you're right, it has something to do with the way you generally move...seems like there's no way's different and feels much better!

The only thing about 'em which is a bit frustrating is the fact that you can't wear 'em all of the time (which I would love to). When you go for a walk in the forest it's certainly not a first choice...and I love nature so much ;-) But if you're out for a short trip, no matter if you go shopping 'round the corner, drive in your car or go by bike...I'll wear them! Took some time to have the 'balls' to do that, now it's a common big deal.

'You're just as pretty as you feel' (sang Grace Slick long ago). What a nice song, keep your heart open...and let go!!

Btw, I'm not that addicted to pointed shoes which keep hurting my toes too my advice for all of you Ladies'n'Ladyboys, go for rounded pumps or peep-toe stilettos!

Very glad to have found your site Lucy, you're such an inspiration!!



Keith on June 09, 2010:

I have a fetish for stillettos.the more i see 4inch or 6inch heels the more i want to wear them.the feeling of wearing them is just amazing.

simon on May 09, 2010:

i would like people that wear high heels to stop using words like "fetish" + "feminine" as it does nothing for the person apart from bolstering up stereotypes that the general public have for men that wear high heels.

each to there own is say

dinkan53 from India on April 19, 2010:

By wearing high heeled shoes quite often, you will get something free for you whole life "back ache"

Related Articles