Unhiding my heels

[mlroseplant]

22 hours ago, pebblesf said:

Good for you buddy, sounds like great times indeed.  

I worry that I have the "turtle thing" and might be guilty of "clumping around" in my boots.  I'm afraid of watching a video of myself, for fear it will discourage me.  But I do realize that the truth can hurt/discourage, but is needed to make long term improvements.  

I can remember the first time I ever saw myself in a full length mirror wearing heels. I was in my early 20s, and I was so horrified by what I saw that I never put on another pair of heels for 15 years. However, times have changed, and now I can look at something and say, "OK, that doesn't look that great. Why? How do I fix this?" I'm not spending time and money to go to a modeling school or some sort of coach like that, so I have to figure it out by myself. Do not be afraid, my friend. You may find out that you don't look nearly as bad as you thought. And if you do, you can fix it!

14 hours ago, Pierre1961 said:

So better not to watch. It’s already difficult enough. No need to have bad  images in our mind. For improvement only good exemples are inspiring 

I agree that you shouldn't spend a lot of time watching people do something badly, but it can be useful. Sometimes, I just need to answer the question, "Why does this person look awkward?" And then not do that!

[pebblesf]

4 minutes ago, mlroseplant said:

I can remember the first time I ever saw myself in a full length mirror wearing heels. I was in my early 20s, and I was so horrified by what I saw that I never put on another pair of heels for 15 years. However, times have changed, and now I can look at something and say, "OK, that doesn't look that great. Why? How do I fix this?" I'm not spending time and money to go to a modeling school or some sort of coach like that, so I have to figure it out by myself. Do not be afraid, my friend. You may find out that you don't look nearly as bad as you thought. And if you do, you can fix it!

I agree that you shouldn't spend a lot of time watching people do something badly, but it can be useful. Sometimes, I just need to answer the question, "Why does this person look awkward?" And then not do that!

Thanks buddy!

[Pierre1961]

You’re right 

But if we make comparisons with sports training:

-watch people who are doing well again and again. Understand why , inspire 

-train and watch yourself, point out what’s wrong , improve 

-if necessary watch someone who is making the same mistakes as you. It can help to understand what’s wrong with you 

Only for this purpose 

[Shyheels]

When I saw myself in heels in a full length mirror - five inch chocolate brown stiletto knee boots with skinny jeans - I was more intrigued than anything else. Yes, startling, but that was what intrigued me. My legs are fit and slender and if one was to see only the bottom half of that image, and therefor nothing that was conclusively male, one would not think anything of it at all. The assumption, because if the heels, would be that it was a woman wearing skinny jeans and stiletto boots. No big deal.

it was only when taking into consideration the top half of the image that it seemed startling. My conclusion from that was that in an absolute sense I do not look bad in stiletto knee boots - it is just the jarring of expectations that sets up an unease and makes one think it doesn’t look right, or looks bad. 
 

it’s all in the mind

[pebblesf]

7 minutes ago, Shyheels said:

When I saw myself in heels in a full length mirror - five inch chocolate brown stiletto knee boots with skinny jeans - I was more intrigued than anything else. Yes, startling, but that was what intrigued me. My legs are fit and slender and if one was to see only the bottom half of that image, and therefor nothing that was conclusively male, one would not think anything of it at all. The assumption, because if the heels, would be that it was a woman wearing skinny jeans and stiletto boots. No big deal.

it was only when taking into consideration the top half of the image that it seemed startling. My conclusion from that was that in an absolute sense I do not look bad in stiletto knee boots - it is just the jarring of expectations that sets up an unease and makes one think it doesn’t look right, or looks bad. 
 

it’s all in the mind

Hmm, well this hits home for sure.  I think I look pretty darn good when I look in the mirror from the waste down.  I'm not impressed when I look at the whole picture though.  

[hiddenheels]

On 9/2/2022 at 3:57 AM, pebblesf said:

Hmm, well this hits home for sure.  I think I look pretty darn good when I look in the mirror from the waste down.  I'm not impressed when I look at the whole picture though.  

Definitely agree. Our mirror is such that if I'm wearing heels, I'm too tall to get my entire reflection in the mirror, my head is outside the mirror, and things usually look good waist-down, but am still not completely comfortable with the entire image. Society's image of what a man/woman should be is deeply ingrained in us I assume.

It has gotten much better over time, and I'm much more comfortable. Look at images online of what women wear, and try to copy those styles that I like, with a modification that above-the-waist it's my normal cloths, below-the-waist it's usually something from the other side of the store.

[hiddenheels]

Wow, time is flying! Haven't posted here in what seems like forever. Have been making good progress, and have received some good feedback. For heels, I've gotten a few skinny torn jeans which I think look awesome, so been wearing them (have them in blue, black and white). I really like this look:

 

Ripped jeans with pumps. So been experimenting with that. Blue jeans, yellow matte 5" pumps. Most recently I've settled onto something like the above image, black jeans, black pumps, white shirt, and a black jacket (it's cold outside!). Once wore this outfit with my 4" pumps, and some guy complimented me, and started asking questions ("how far do you live", "come here often", etc); the conversation didn't last long as I didn't feel comfortable.

Recently I felt adventurous. 4" pumps were easy to wear, but have another with 5" heels, matte black, so I thought what the heck, and went with those. Parked by a mall, shopped around, went to the other side of the mall to a coffee shop, did some work, then more shopping, total 2 hours? Standing in line at the coffee shop, this lady comes up to me telling me how I "rock" those heels, and she couldn't do it. The compliment felt good, was really appreciated.

Wore the same outfit yesterday at a different mall, after about 3 hours I was tired, both of my errands, and my feet. Need to get my endurance up a bit. But I felt great, and still am feeling great!

It's so nice to be out and about, presenting myself how I feel comfortable. In guy cloths, I'm invisible. So these compliments are certainly noticed!

[Jkrenzer]

Great to here you're wearing, love to see you in them not some model though.

[mlroseplant]

Take it a little easy on him, it's February, and he's from Canada. I haven't been taking any pictures lately, either. Way too cold to be modeling skinny jeans, especially those with holes already in them! Give us a couple of months.

[hiddenheels]

Have serious issues posting photos of myself on the internet, so as much as I would like to share this, I cannot. If I can come up with a creative way of doing so, such that someone close to me would not recognize the photo of me, I will. In the meantime, I'm sorry.

-------------------

Had a chance to go to another mall today, was looking for something specific that is only in that mall. Anyway, was way too obsessed with my new pumps to not give it a go. Tried them on in the morning, and was sad to see that they did not fit too well, was a bit too small...? Thought feet expand during the day. I still wanted to try them out, they're so gorgeous. So drove to the mall, same skinny jeans, white top & black jacket. Got out of the car and started walking, no butterflies. Very quickly noticed that the pumps were oh so comfortable! In terms of comfort, they were beyond expectation. I was surprised. Is it because of the leather? I know the shoe must fit properly, but still.. I have other shoes that fit, but aren't this comfortable.

This mall has the same store as where I bought the black Steve Madden pumps I mentioned above. Went to the store, just to check it out. To my surprise, they had a bunch of "nude" versions! Same Vala, leather! And they had my size! I couldn't resist, bought that as well. Haven't unboxed it yet.

Did what I needed to do at the mall, then went to a coffee shop for lunch. The pumps are super-comfortable. I'm happy.

Also happy since there are no more butterflies. Love the look, skinny jeans & pumps. Maybe I'll work up to skinny jeans and boots in the near future!

[mlroseplant]

6 hours ago, hiddenheels said:

Have serious issues posting photos of myself on the internet, so as much as I would like to share this, I cannot. If I can come up with a creative way of doing so, such that someone close to me would not recognize the photo of me, I will. In the meantime, I'm sorry.

-------------------

Had a chance to go to another mall today, was looking for something specific that is only in that mall. Anyway, was way too obsessed with my new pumps to not give it a go. Tried them on in the morning, and was sad to see that they did not fit too well, was a bit too small...? Thought feet expand during the day. I still wanted to try them out, they're so gorgeous. So drove to the mall, same skinny jeans, white top & black jacket. Got out of the car and started walking, no butterflies. Very quickly noticed that the pumps were oh so comfortable! In terms of comfort, they were beyond expectation. I was surprised. Is it because of the leather? I know the shoe must fit properly, but still.. I have other shoes that fit, but aren't this comfortable.

This mall has the same store as where I bought the black Steve Madden pumps I mentioned above. Went to the store, just to check it out. To my surprise, they had a bunch of "nude" versions! Same Vala, leather! And they had my size! I couldn't resist, bought that as well. Haven't unboxed it yet.

Did what I needed to do at the mall, then went to a coffee shop for lunch. The pumps are super-comfortable. I'm happy.

Also happy since there are no more butterflies. Love the look, skinny jeans & pumps. Maybe I'll work up to skinny jeans and boots in the near future!

Three thoughts on my end: 1) I know it's contrary to what every single shoe advisor tells us, but I have always found that my feet are bigger in the morning. I have also found that my feet have shrunk half a size as I've gotten older. That is never supposed to happen, either.

2) I hate to be the bearer of bad news, but none a them Steve Madden pumps are leather. You'd have to go back at least 10 years to find SMs made of leather. They're made to a price point, after all. That's not to say they aren't a decent quality shoe, but they're not leather, as least not the pumps. Some of the sandals might still be leather, but I doubt it.

3) I know I'll catch a lot of flak for this, and that's fine, but I have never understood this "moving up to boots" business. It seems to me that boots are the easy ones to wear as a guy. It's the pumps and sandals, the more delicate footwear, that is a step up in boldness. Of course, some people actually like boots. Some people are very enthusiastic about boots. I happen to not be one of those people.

[Shyheels]

6 hours ago, hiddenheels said:

Have serious issues posting photos of myself on the internet, so as much as I would like to share this, I cannot. If I can come up with a creative way of doing so, such that someone close to me would not recognize the photo of me, I will. In the meantime, I'm sorry.

-------------------

Had a chance to go to another mall today, was looking for something specific that is only in that mall. Anyway, was way too obsessed with my new pumps to not give it a go. Tried them on in the morning, and was sad to see that they did not fit too well, was a bit too small...? Thought feet expand during the day. I still wanted to try them out, they're so gorgeous. So drove to the mall, same skinny jeans, white top & black jacket. Got out of the car and started walking, no butterflies. Very quickly noticed that the pumps were oh so comfortable! In terms of comfort, they were beyond expectation. I was surprised. Is it because of the leather? I know the shoe must fit properly, but still.. I have other shoes that fit, but aren't this comfortable.

This mall has the same store as where I bought the black Steve Madden pumps I mentioned above. Went to the store, just to check it out. To my surprise, they had a bunch of "nude" versions! Same Vala, leather! And they had my size! I couldn't resist, bought that as well. Haven't unboxed it yet.

Did what I needed to do at the mall, then went to a coffee shop for lunch. The pumps are super-comfortable. I'm happy.

Also happy since there are no more butterflies. Love the look, skinny jeans & pumps. Maybe I'll work up to skinny jeans and boots in the near future!

Skinny jeans and boots makes a great combination.

Self capture photography can be tricky, especially if you are looking to make high quality images as you have to be, in effect, model, photographer, stylist and director all at the same time, and if you’re striving for anonymity as well it becomes trebly hard. I have some experience at this, having shot a project where a degree of anonymity was necessary for artistic reasons - the story behind the images was not meant to be about me personally - and it takes a lot of thought. Images where details such as heels are supposed to play a prominent visual role would really be tricky. 

 

7 minutes ago, mlroseplant said:

Three thoughts on my end: 1) I know it's contrary to what every single shoe advisor tells us, but I have always found that my feet are bigger in the morning. I have also found that my feet have shrunk half a size as I've gotten older. That is never supposed to happen, either.

2) I hate to be the bearer of bad news, but none a them Steve Madden pumps are leather. You'd have to go back at least 10 years to find SMs made of leather. They're made to a price point, after all. That's not to say they aren't a decent quality shoe, but they're not leather, as least not the pumps. Some of the sandals might still be leather, but I doubt it.

3) I know I'll catch a lot of flak for this, and that's fine, but I have never understood this "moving up to boots" business. It seems to me that boots are the easy ones to wear as a guy. It's the pumps and sandals, the more delicate footwear, that is a step up in boldness. Of course, some people actually like boots. Some people are very enthusiastic about boots. I happen to not be one of those people.

I agree with you about boots - they are much easier to wear as a guy, more masculine in nature than dainty strappy things. To be sure, it is easier to hide shoes, especially if your style is to wear boots outside skinny jeans, but in general I think it is far easier for a guy to get away with boots, especially with block heels.

[hiddenheels]

7 hours ago, mlroseplant said:

2) I hate to be the bearer of bad news, but none a them Steve Madden pumps are leather. You'd have to go back at least 10 years to find SMs made of leather. They're made to a price point, after all. That's not to say they aren't a decent quality shoe, but they're not leather, as least not the pumps. Some of the sandals might still be leather, but I doubt it.

Write more later, but just quickly, the thing is advertised as Leather, it's imprinted inside the shoe along with the size. These heels cost $125CAD, would expect them to be leather. Can you clarify? These are it: https://www.stevemadden.ca/products/vala-black-leather

[Cali]

11 hours ago, mlroseplant said:

3) I know I'll catch a lot of flak for this, and that's fine, but I have never understood this "moving up to boots" business. It seems to me that boots are the easy ones to wear as a guy. It's the pumps and sandals, the more delicate footwear, that is a step up in boldness. Of course, some people actually like boots. Some people are very enthusiastic about boots. I happen to not be one of those people.

Here's an opinion from a guy who wears them all, from delicate sandals to knee high boots, long pants to short shorts.  Wear tall boots with block heels under your pants is very easy, no harder than booties with block heels.  I think this is starting to become mor acceptable. But once you wear boots on the outside, it starts to change.  And when you wear 4 (net) inch knee high stlettos outside your jeans or with short shorts it gets bolder.  Add in some leggins ...

Is it as bold as stilleto pumps, I have no experiences there.  Pumps hate my feet.  But ankle lenght jeans and this boot (at work) is bold.

Or this knee high

[pebblesf]

20 hours ago, hiddenheels said:

Have serious issues posting photos of myself on the internet, so as much as I would like to share this, I cannot. If I can come up with a creative way of doing so, such that someone close to me would not recognize the photo of me, I will. In the meantime, I'm sorry.

-------------------

Had a chance to go to another mall today, was looking for something specific that is only in that mall. Anyway, was way too obsessed with my new pumps to not give it a go. Tried them on in the morning, and was sad to see that they did not fit too well, was a bit too small...? Thought feet expand during the day. I still wanted to try them out, they're so gorgeous. So drove to the mall, same skinny jeans, white top & black jacket. Got out of the car and started walking, no butterflies. Very quickly noticed that the pumps were oh so comfortable! In terms of comfort, they were beyond expectation. I was surprised. Is it because of the leather? I know the shoe must fit properly, but still.. I have other shoes that fit, but aren't this comfortable.

This mall has the same store as where I bought the black Steve Madden pumps I mentioned above. Went to the store, just to check it out. To my surprise, they had a bunch of "nude" versions! Same Vala, leather! And they had my size! I couldn't resist, bought that as well. Haven't unboxed it yet.

Did what I needed to do at the mall, then went to a coffee shop for lunch. The pumps are super-comfortable. I'm happy.

Also happy since there are no more butterflies. Love the look, skinny jeans & pumps. Maybe I'll work up to skinny jeans and boots in the near future!

I'm so envious, I'll bet you look amazing...

[mlroseplant]

16 hours ago, hiddenheels said:

Write more later, but just quickly, the thing is advertised as Leather, it's imprinted inside the shoe along with the size. These heels cost $125CAD, would expect them to be leather. Can you clarify? These are it: https://www.stevemadden.ca/products/vala-black-leather

Well I'll be! They DO appear to be leather. Have never seen such a thing Stateside, and Uncle Google seems to be silent about the matter. Not that I spent a great deal of time attempting to research the matter. I'm curious a bit, but not too much so, because I have plenty enough Steve Madden pumps already. It is difficult for me to imagine a situation where I would be wearing pumps for more than a few hours at a time, so the leather construction is less of a factor for me. However, it's good to know that SM still offers leather pumps to some degree.

[Shyheels]

11 hours ago, Cali said:

Here's an opinion from a guy who wears them all, from delicate sandals to knee high boots, long pants to short shorts.  Wear tall boots with block heels under your pants is very easy, no harder than booties with block heels.  I think this is starting to become mor acceptable. But once you wear boots on the outside, it starts to change.  And when you wear 4 (net) inch knee high stlettos outside your jeans or with short shorts it gets bolder.  Add in some leggins ...

Is it as bold as stilleto pumps, I have no experiences there.  Pumps hate my feet.  But ankle lenght jeans and this boot (at work) is bold.

Or this knee high

It’s a good point you make about wearing boots outside jeans - it is certainly a bold move and all the more so with stilettos. 

[mlroseplant]

11 hours ago, Cali said:

Here's an opinion from a guy who wears them all, from delicate sandals to knee high boots, long pants to short shorts.  Wear tall boots with block heels under your pants is very easy, no harder than booties with block heels.  I think this is starting to become mor acceptable. But once you wear boots on the outside, it starts to change.  And when you wear 4 (net) inch knee high stlettos outside your jeans or with short shorts it gets bolder.  Add in some leggins ...

Is it as bold as stilleto pumps, I have no experiences there.  Pumps hate my feet.  But ankle lenght jeans and this boot (at work) is bold.

Or this knee high

I suppose we could argue about this until the cows come home, but a guy wearing boots on the outside of his pants is a fairly common sight around here. A guy in boots with heels is not. To my mind, it's a smaller step (no pun intended) to wear boots with heels than it is to wear pumps with heels. Maybe guys do not typically wear boots on the outside of their pants out there on the West Coast, and perhaps that is where our differing opinions originate.

[Cali]

How about the guy that wears knee high stilettos in the summer with short shorts?

What is bold somewhere might be normal in other places.  And what someone thinks is bold might be old hat to others.

Walking in pumps in a mall and walking in pumps at work are very different.  One place is with strangers, the other is with people that know you and see you everyday.  I shopped in a large and busy shopping mall in wedges (4 inch) and compression/performance leggings the other day. I felt tht was bold.  And I got many second, third, fourth looks.

For now, walking in 4 inch heels is bold.

Edited February 12, 2023 by Cali

[Shyheels]

The boots that guys more typically wear outside their jeans are work boots, not fashion boots - an entirely different thing. 

[Puffer]

11 hours ago, mlroseplant said:

I suppose we could argue about this until the cows come home, but a guy wearing boots on the outside of his pants is a fairly common sight around here. A guy in boots with heels is not. To my mind, it's a smaller step (no pun intended) to wear boots with heels than it is to wear pumps with heels. Maybe guys do not typically wear boots on the outside of their pants out there on the West Coast, and perhaps that is where our differing opinions originate.

An 'undecorated' boot, of any style up to knee-high, is essentially an item of practical weatherproof/protective footwear, even if worn as a fashion choice, and therefore intrinsically 'male' in its origins and impact.   But, if it has anything beyond a flattish or fairly low cuban/cowboy heel, it ceases to hide behind that facade.

A 'court' shoe (pump), although historically male wear, is in its modern-day iteration wholly female footwear, regardless of the height or style of heel.

It follows that a man wearing (long) boots, with or without modest heels and even if outside his trousers, is unlikely to register much on the CD/eccentric/fetish scales - but a man wearing even the plainest kitten-heeled pump in plain view will set the bells ringing and the tongues wagging.   The saddest thing, however, is that almost any woman can wear any of those things with anonymity and impunity - as long as she doesn't fall over.

[Shyheels]

Tall boots are theatre - and men are not allowed theatre in dress. Where there is a practical need for tall boots - horse-riding or motorcycling, men are given leave to wear them within those circumstances. A man wearing riding boots (pr similar style) in a horsey environment is perfectly fine - although he best have a horse present, or at least be the owner of one, and not just a spectator. And whe he leaves that horsey environment, off come the boots. To wear them outside those confined circumstances would be theatricaland that is not allowed

A woman on the other hand can wear a riding boot style anywhere she pleases, any time, and be considered fashionable.   

[Puffer]

4 hours ago, Shyheels said:

Tall boots are theatre - and men are not allowed theatre in dress. Where there is a practical need for tall boots - horse-riding or motorcycling, men are given leave to wear them within those circumstances. A man wearing riding boots (pr similar style) in a horsey environment is perfectly fine - although he best have a horse present, or at least be the owner of one, and not just a spectator. And whe he leaves that horsey environment, off come the boots. To wear them outside those confined circumstances would be theatricaland that is not allowed

A woman on the other hand can wear a riding boot style anywhere she pleases, any time, and be considered fashionable.   

I agree in principle that 'men are not allowed theatre in dress', although the threshhold is not easy to define.   After all, a modestly-pointed toe, a gold snaffle on a loafer or a strap around a boot are all pure theatre but 'permitted' and certainly tolerated.   My point was not so much what was permitted or expected as conventional male footwear but what would likely incur some sort of reaction if it was worn in public without obvious justification.   

Tall boots worn outside the clearly practical sphere (protection, weather resistance, uniform) would likely get a second glance, even if of a plain flat-heeled style, but scarcely condemnatory.   And you have often told us that you wear OTK boots in public without obvious reaction.

[Shyheels]

Indeed I do wear OTK boots without obvious reaction. I am talking about a general principle that men do not engage in theatre when it comes to fashion. I think the reason that more men do not wear tall boots is that this bias against theatre has become ingrained into the thinking.

[Cali]

Judging by the number of men who give me positive compliments when I wear tall boots, I think more men want to wear them but don't because of societal pressure.

[at9]

When I've worn my (plain black, about 2.5" block heel) knee high boots over leggings I've had a few compliments and more than a few glances. The other day a woman in central London made a somewhat sarcastic comment. It was after we had passed in the street, it came from behind me, so I can't be 100% sure if it was aimed at me.

It's my 3" heel leopard print ankle boots, worn under trousers, that have resulted in many nice comments. And no bad ones yet.

[Shyheels]

It never ceases to amaze me that people seem to think they can make loud sarcastic comments about somebody elses look or manner of dress.  

[hiddenheels]

On 2/11/2023 at 3:35 AM, mlroseplant said:

3) I know I'll catch a lot of flak for this, and that's fine, but I have never understood this "moving up to boots" business. It seems to me that boots are the easy ones to wear as a guy. It's the pumps and sandals, the more delicate footwear, that is a step up in boldness. Of course, some people actually like boots. Some people are very enthusiastic about boots. I happen to not be one of those people.

Moving up to boots... I really do love boots too, and I probably have more ankle boots than pumps. I started with full knee-length boots, under jeans, then started to prefer ankle boots, and those are still probably my favourite. But I wear them under jeans, just the look I've gone for in the past.

More recently, as I've become more comfortable wearing ankle boots, I've started experimenting with pumps, but those I don't prefer under jeans (although they look OK), so ended up buying skinny jeans to match. That was an obstacle (internally, to wear pumps with skinny jeans), but getting the hang of that slowly. But I've never gotten around to experimenting with skinny jeans and boots. So "moving up to boots" I think is not necessarily a moving up in a sense of difficulty, but rather trying to figure out how to fashion it. Need to experiment, but am not sure how well skinny jeans and ankle boots go together. And I think I only have 2 knee-high boots?

I do agree with the general sentiment of the responses here that these shoes are noticeable, if they have a heel more than ~1", and stilettos certainly. However, I'm trying to wear what I like, so it'll likely be high stilettos. And as to why "men don't engage in theatre" when it comes to fashion, I don't know... If anyone argues, then women can wear whatever they want, and we (are supposed to) have gender equality, so f off. Equality doesn't just go one way.

Having said all of this, the worst comment I've heard was some guy walking behind me towards an escalator commenting "hope you don't have to run in those". Not a comment I would consider mean. Otherwise, I've only received good wholesome comments, all from women.

Edited February 13, 2023 by hiddenheels

[Cali]

@hiddenheels,

You need to experiment with skinny jeans and pumps.  Not all skinny jeans are the same.  First you have rise, super high, high, mid, low.  Then there is lenght; I have different lenght skinny jeans, above the ankle and at the ankle are just two of them, 24" 27.5" 28", 29", etc.  If your boot is tight at the ankles, then you want a shorter jean, less material around the ankle. It also depends on where the shoe ends and the jeans begins and how much space between the two you want.

So it depends on the look you want, the theatre.  I'm a little bit bold and have almost everything BUT pumps. 

[Shyheels]

8 hours ago, hiddenheels said:

Moving up to boots... I really do love boots too, and I probably have more ankle boots than pumps. I started with full knee-length boots, under jeans, then started to prefer ankle boots, and those are still probably my favourite. But I wear them under jeans, just the look I've gone for in the past.

More recently, as I've become more comfortable wearing ankle boots, I've started experimenting with pumps, but those I don't prefer under jeans (although they look OK), so ended up buying skinny jeans to match. That was an obstacle (internally, to wear pumps with skinny jeans), but getting the hang of that slowly. But I've never gotten around to experimenting with skinny jeans and boots. So "moving up to boots" I think is not necessarily a moving up in a sense of difficulty, but rather trying to figure out how to fashion it. Need to experiment, but am not sure how well skinny jeans and ankle boots go together. And I think I only have 2 knee-high boots?

I do agree with the general sentiment of the responses here that these shoes are noticeable, if they have a heel more than ~1", and stilettos certainly. However, I'm trying to wear what I like, so it'll likely be high stilettos. And as to why "men don't engage in theatre" when it comes to fashion, I don't know... If anyone argues, then women can wear whatever they want, and we (are supposed to) have gender equality, so f off. Equality doesn't just go one way.

Having said all of this, the worst comment I've heard was some guy walking behind me towards an escalator commenting "hope you don't have to run in those". Not a comment I would consider mean. Otherwise, I've only received good wholesome comments, all from women.

Like you I like ankle boots a lot - to me they are like edgier, sportiier versions of the hiking boots I've worn since  days as a geology student back in university. I've always preferred boots to shoes, with hiking boots being my standard attire for decades. And happily in my line of work I've been able to get away with it.  Adding a three-inch block or cuban heel feels wonderfully racy. Finding the right ankle boots, in my size, is tricky. I've two pair, from Shoes of Prey, which I likea lot. Wearing them with skinny jeans works all right - women do it all the time - although I think I find I prefer boot-cut jeans with ankle boots. I wea skinny jeans a lot though as they work best with my knee and OTK boots.

Yes, we're supposed to have gender equality, but to adapt a quote from Napoleon the Pig says in Animal Farm, some genders are more equal than others. And so liberality and theatre in fashion go only one way. Manly men are expected to remain with the herd, keep self expression to a minimum and adopt a scornful attitude towards frivolity.