"How Can You Wear Those Heels?"

Discussion of fashion elements and looks that are traditionally considered somewhat "femme" but are presented in a masculine context. This is NOT about transvestism or crossdressing.
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JeffB1959
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"How Can You Wear Those Heels?"

Post by JeffB1959 »

While I was out and about on Saturday, I had a woman walk up to me and ask how I could stand in the four inch heels I was wearing. In all the years I've been publicly wearing women's clothing (close to twenty and counting), that's THE one question I've been asked most, especially by women who look perplexed, even awed at my accomplishment, as if what I did defied the laws of physics. My answer to her consisted of just one word: "Practice".

Being asked that question always makes me chuckle because it seems so silly to me. That leads me to suspect women believe men are inherently incapable of standing, much less walking in high heels, in THEIR shoes, and when they see men like me pulling off that feat, they have trouble accepting that reality. For me, it's no impossible task, I've been wearing heels since I was thirteen when I wore a pair of my mother's shoes to satisfy my curiosity over how she could walk in them. Once I discovered it wasn't all that hard (after some practice), it became great fun, and I've been strutting around in heels like in the picture below ever since.

Perhaps women who pose that question think men lack some genetic ability to master the feat of wearing heels, the simple truth isn't earth shattering: it's not that hard. Really. If women can do it, so can men. Plain and simple. That's the answer.
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Mouse
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Re: "How Can You Wear Those Heels?"

Post by Mouse »

I concur, wear a fantastic skirt and some heels, people will notice the heels first and comment on them, way before getting to the skirt. I was on a platform in full latex, skirt and all, and the question asked was "how can you walk in those heels?" I used the same response as you "practice" and like you have been absorbed in trying feels from a small boy.
Image
I still admire women who can walk well in heels and wonder why more women do not get good at them. I know having heels on your feet, makes running away harder, I feel that when I am in tough areas. But for getting attention, heels do that in spades.

I once had a long conversation with a couple of women in Tesco's who were marveling at my heels and me walking in them. One woman came out with the line, "I could never wear a pair of heels like that, it would kill my husband!!!" I responded that she should try a pair and I was sure that he would lover her for it.
Last edited by Uncle Al on Mon Mar 30, 2026 7:42 pm, edited 1 time in total.
Reason: changed commit to comment
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kingfish
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Re: "How Can You Wear Those Heels?"

Post by kingfish »

20220310_124920_1.jpg
I've gotten that same question and produced pretty much the same answer.
I'd also say that it's doable by them too, and then describe how I got to being able to wear them all day without pain.
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JohnH
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Re: "How Can You Wear Those Heels?"

Post by JohnH »

Here, I'm almost 74 years of age, and I wear 75 mm (3 inch) heels. Very few women of my age wear heels that high. So, yes, men CAN wear heels.
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JeffB1959
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Re: "How Can You Wear Those Heels?"

Post by JeffB1959 »

kingfish: That photo looks terrific!

JohnH: Bravo to you!
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Kirbstone
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Re: "How Can You Wear Those Heels?"

Post by Kirbstone »

Jeff,
I expect that with your actual height and four inches added, the lady's comments would have probably been directed at your navel !

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Susie
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Re: "How Can You Wear Those Heels?"

Post by Susie »

JeffB1959 wrote: Mon Mar 30, 2026 10:55 am
Being asked that question always makes me chuckle because it seems so silly to me. That leads me to suspect women believe men are inherently incapable of standing, much less walking in high heels, in THEIR shoes, and when they see men like me pulling off that feat, they have trouble a
Women are more likely to be in awe and jealous of your ability to wear heels confidently - I know I was of Mouse!
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GerdG
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Re: "How Can You Wear Those Heels?"

Post by GerdG »

I prefer sneakers!
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CamperGuy
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Re: "How Can You Wear Those Heels?"

Post by CamperGuy »

A few years ago, I could never have imagined being interested in heels. I used to wear tights under shorts all the time and that seemed to be a completely different style territory.

But trying and falling in love with mini skirts has changed all that. I most often wear skirts with plimsoles / trainers but then fancied trying them with women's flat shoes. I love the look of T-strap / mary jane shoes (although some of these come in fairly chunky designs which I don't like), plus ankle-strap flats, so I bought a couple of pairs and loved them, having worn them in public a few times. But then when looking for more T-strap shoes I came across some with a 2-inch block heel, and became interested in the idea of trying heels. I bought a pair and love them. I've worn them out a few times (I'm wearing them as I type this).

I also really wanted a set of brown T-strap shoes, in more of a classic 1940s look. I found some really nice brogue style ones. I was a bit worried as they had a 3" heel, but when they arrived and I tried them I was over the moon.

They look fantastic and I think they look great on me with a mini skirt and black tights - they make your legs look longer and slimmer. The extra height looks good, although I can definitely feel it and it will take a bit more getting used to. The 2" heels now feel almost flat by comparison.

So, I am a convert, although I am not sure I would go as far as stiletto heels or sandals. I like that classic 1940s look and a block (although not too chunky) heel.

Looking forward to finding more occasions where I can wear the heels out (I am still careful about being seen by friends and family).

Camperguy.
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JeffB1959
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Re: "How Can You Wear Those Heels?"

Post by JeffB1959 »

Kirbstone: HA! Good one! Actually, at six foot two plus four inchers, I kinda am scraping the sky! :lol:

Susie: To be honest, I hardly expect women to be awed or jealous of me. That's something I truly don't expect.
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Mouse
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Re: "How Can You Wear Those Heels?"

Post by Mouse »

Susie wrote: Mon Apr 20, 2026 6:41 pm Women are more likely to be in awe and jealous of your ability to wear heels confidently - I know I was of Mouse!
Susie, Thank you. The thing I try to be with heels is confident.
GerdG wrote: Tue Apr 21, 2026 4:46 am I prefer sneakers!
Good choice for getting about.
CamperGuy wrote: Tue Apr 21, 2026 6:10 am A few years ago, I could never have imagined being interested in heels........
As soon as I started wearing skirts in public, my brain immediately went to freeing up what I put on my feet. Skirts offer so much more choice as to what to wear on your feet. Problem is, once you start looking at boots and shoes designed for women, you find endless choice and heels come into the picture. It did not help that I have loved women in heels all of my life, so getting heels of my own has been brilliant.
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MrSoapsud
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Re: "How Can You Wear Those Heels?"

Post by MrSoapsud »

JeffB1959 wrote: Tue Apr 21, 2026 8:13 am Kirbstone: HA! Good one! Actually, at six foot two plus four inchers, I kinda am scraping the sky! :lol:
I went to a "drag night" recently (interesting experience) and I believe the performer was about 7 foot tall in their heels!
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