Advice for a guy who is new to wearing heels

Every now and then, guys will reach out to me for advice on how to move forward with their own fascination with tights and / or heels.  

Here is a recent one.  I’ve made some small edits for spelling and clarity. In this dialogue, he’ll be referred to as AF. 

Being a guy in nylons and heels has been one of the most instructive things of my life. I’ve learned so much about my relationship to fear, the human condition, and the cost / benefit analysis of being authentic. 

I also know a ridiculous amount about the finer points of hosiery – you can check out my reviews of some of my favorite brands & styles here, if you are curious. 

One thing I’ve learned is how common it is for men to become curious about certain ladies things.  Dear reader, I assure you that you have at least one very “manly man” in your life who has a secret drawer of lacy little things and secrets he’ll take to his grave.

And what’s not to be curious about? Humans, at their best, are curious creatures. It’s why we travel and love foreign food restaurants. The feminine is fascinating. Ultimately, I think a guy being intrigued by something in his wife’s closet is about as remarkable as my fetish for chicken tikka masala or birria tacos. 

In the spirit of shedding some compassionate light on that, I share this dialogue: 

Anonymous Friend: Hey man, just wanna say you are an inspiration to me. I want to build my self to wear my high heels, leggings, and other stuff like that in public cause I find myself smiling and enjoying myself a lot more. If you’ve got any advice or tips for me I’d really appreciate it.

Paul Duane: Hi there, first of all, thank you for the compliment. Very gracious of you. As for advice – honestly…. I don’t advise it. lol.

I’m curious, what motivates you to want to do this?

AF:  I just have decided that clothing or shoes shouldn’t be gendered and they should be chosen by whoever wants to wear them. I’m a heterosexual man as well. I just want to feel open and free and stop letting myself get caught in what others think about gender conforming.  I find it stupid, as it limits fashion choices

PD: Ok thats the first layer of the onion. That’s what you tell your family to justify your decisions. 😉
But really. What’s up?

AF: Nothing’s up, and my family’s opinion on this don’t mean shit to me, as I don’t give a rat’s ass about what their ignorant Christian ass thinks about my Gender Non-conformist lifestyle.

PD: Sounds like you have a lot of emotion about this topic.

AF: No I just think it’s stupid for people to really care about what others wear on their body, regardless of gender. Grown ass people who worry about what others wear on they own body when there are worse things going on in society, is immature and idiotic.

PD: Ok. I’m prepared to give you my advice now. Ready?

AF:  👍

PD: In my experience – I have found it absolutely crucial, to have the mindset of allowing people to hate what I wear. Allowing people to disagree.  When I walk out the door in nylons & heels, I am acutely aware that I am breaking all kinds of societal norms and challenging many people’s ideas of “right” and “wrong”.  I have found that it’s extremely important to allow people to feel the way they do about it.   I must give them the grace that I hope they’ll give me.

That said – I invite you to have a lot of empathy for people who will think what you are doing is wrong / stupid / unattractive / etc etc etc.   Be okay with it.

AF:  Oh yeah, I’m okay with it. I just hope people will one wake up.

PD: You’ve gotta be okay with them not “waking up”.  There’s not a right or wrong answer here. You cannot have a stance of moral superiority about this.

AF:  Someone else told me you seemed conservative about this topic, which it sounds like you are, but they said, just to send you a message still.

PD: That’s so interesting. Conservative in what way?

AF:  Idk what way, they just told me you seemed against the whole thing even though you wear nylons and heels, which would be sort of hypocritical imo- but I understand everyone has a different view of something like this.   I don’t mean it in a bad way, I just thought it was weird that this person who I talked to on Facebook, was telling me about you, and said you seemed conservative about this topic, lol.

PD: LOL I do have a nuanced point of view, for sure.  For instance:

I absolutely disagree with the idea of removing gender designations from things. Some want to say these are “non-gendered heels” rather than “women’s heels”.  I think that’s misguided.  For example,  Let’s say I invite you to lunch, and I tell you we are going for ‘tortilla based food’.

You may ask WTF I am talking about, and then soon realize I’m talking about Mexican food.

If I were to respond, “I’d really prefer that we just refer to it as ‘tortilla based food’.  Tacos are non-national”, and at some point, you might start to observe that I’m really uncomfortable with the word “Mexican”.  What might you conclude about me?

AF:  Oh, I don’t care as I’m a person who understands everyone and everything has its own opinions or way of seeing things differently, which is what makes all unique or different in our own way

PD: Back to my question…. if I was weird about the word “Mexican”, what might you assume about me?

AF:  Idk that you might be prejudice towards the word Mexican or Mexican people but idk as I’m not really good with these things, lol

PD: Exactly.

Do you listen to Madonna much?

AF:  No as that’s not really the type of music I find enjoyable as I grew up around rap such as drill/trap Biggie, Nipsey Hussle, etc.

PD:  Ok, all good. I want you to listen to the first 30 seconds of this song:

"Girls can wear jeans and cut their hair short, Wear shirts and boots 'cause it's okay to be a boy But for a boy to look like a girl is degrading 'Cause you think that being a girl is degrading But secretly you'd love to know what it's like wouldn't you... What it feels like for a girl"

AF:  Ok

PD:  I love wearing women’s heels and women’s hosiery. I love it for a dozen reasons.

AF:  Yeah, same, but I just enjoy the heels.

PD:  So…. in a nutshell – my advice is:

  1. Be okay with people NOT being okay with you. Don’t be mad at them.
  2. Be okay with them being women’s things. Own it. It’s okay to borrow stuff from the women’s department sometimes. If that’s hard for you….. then yes, there’s something deeper going on here that you could look at.

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