Seen out and About

[Cali]

1 hour ago, bluejay said:

I too love wearing both my leather pants and leather leggings. I even have a leather mini dress and leather skort that I wear in warmer weather. I love the look and feel of leather real or imitation.

Happy Heeling,

bluejay

I too have a faux leather skirt.

[higherheels]

20 hours ago, mlroseplant said:

I'm trying to think if I've ever seen somebody around here wearing leather pants who wasn't riding a motorcycle.

In Germany they're worn quite frequently, also by me. But only by women, men here only wear them for riding a motorcycle as you say 😉

 

20 hours ago, mlroseplant said:

Ten years ago, I wouldn't have cared, but now I kind of want to know why someone besides me would wear heels to the grocery store.

What a pity. Nowadays I also immediately have a look if I hear a pair of heels somewhere. It became a rare occasion.

[Shyheels]

It’s a pity that men seem to be so restricted in what society permits them to wear. It’s the same with knee boots - fine if there’s a horse or motorcycle in the picture, but otherwise wearing them is considered odd or effeminate. Strange, really.

As for me I rather like the idea of wearing leather trousers with heels.

[higherheels]

I think in the 90s and early 2000s it wasnt't that uncommon for men to wear leather pants, right?

Fashion standards are strange...

[Shyheels]

8 minutes ago, higherheels said:

I think in the 90s and early 2000s it wasnt't that uncommon for men to wear leather pants, right?

Fashion standards are strange...

They certainly are. The history of fashion is quite an interesting topic. Until I got brave enough to try wearing heels, I never really considered the history and meanings of fashion before. The history of heels is fascinating

And you’re right in the 90s and 00s it was not uncommon for men to wear leather trousers - even without a motorcycle!

[Cali]

In early November I flew in a pair of faux leather pants and knee high JS 4 inch boots. Only one at the airport in leather pants and one of the very few in heels. Be aware @Shyheels if you wear this look, you WILL be noticed. So dress smartly.

[Shyheels]

I always try to dress smartly when I’m in heels and I would do the same with leather trousers. I like contrasts in textures so I would wear them with a wool jumper or something like that 

[pebblesf]

19 hours ago, Cali said:

In early November I flew in a pair of faux leather pants and knee high JS 4 inch boots. Only one at the airport in leather pants and one of the very few in heels. Be aware @Shyheels if you wear this look, you WILL be noticed. So dress smartly.

You are right, you will definitely be noticed.  Most won't say anything, but you will feel many stares in your direction.  So, having confidence in what you are wearing, and how you look is so necessary.  We have to remember that many disapproving looks are truly just envy, whether they come from men or women.  The important thing is how you feel about how you look.  In my case, I have to be honest with myself, no way I can pull off many of the outfits I might like to wear, this old dad bod just isn't up to it.  But, I still think I look pretty good in some nice boots over tight fitting levis or girl jeans.  So, over the years my confidence has increased.  I can honestly say that I think I look good, and that is all that matters.  Needless to say, recieving an occasional compliment refuels my confidence, don't mind admitting that.  

The other thing to remember is it is important to dress appropriately for the occasion/audience.  A tight skirt/hose/tall heels probably isn't appropriate for a football stadium or Home Depot.  Cali's advice about "dressing smartly" is very important indeed. 

My best to all my HHP buds for a happy holiday season and healthy 2026!  Don

[CrotchHigh]

I agree with you both on this, as I travel a lot and wear my high heeled boots to many different locations.  If you dress for the proper occasion and for the right place, the compliments will come.  I luckily have only received compliments from guys and women when I wear my boots.  There are a lot of guys and out there that want to and wish they could wear boots and heels like the rest of us.

[Shyheels]

I’ve no doubt at all about that. I think guys in general are weary of the stifling rules for men’s fashion regarding colours and styles, and would like to inject a bit of theatre into their personal style 

Edited December 24, 2025 by Shyheels

[Cali]

1 hour ago, CrotchHigh said:

I agree with you both on this, as I travel a lot and wear my high heeled boots to many different locations.  If you dress for the proper occasion and for the right place, the compliments will come.  I luckily have only received compliments from guys and women when I wear my boots.  There are a lot of guys and out there that want to and wish they could wear boots and heels like the rest of us.

I figure at least 10% of the guys who compliment me on my heels wish they had the cojones to wear high heel knee high boots.

[mlroseplant]

Over the weekend, my son's high school jazz band performed at a festival. They did well. The trombone section has taken to wearing pink shoes as of late. 3 out of the 4 of them now wear such for every concert. Times have changed. There's no way a boy could have gotten away with wearing pink shoes and lived to tell the tale back in my day.

[Shyheels]

Yes that’s true. I could never understand this bias against pink for men. Even back in my university days, long before I gathered the courage to wear high heeled boots, I was more than happy to wear pink. I remember my grandmother being appalled by my wearing a pink shirt once. I don’t recall ever seeing pink shoes, let alone pink hiking boots - hiking boots were all I ever wore back then.

 

[pebblesf]

On 12/24/2025 at 11:32 AM, Cali said:

I figure at least 10% of the guys who compliment me on my heels wish they had the cojones to wear high heel knee high boots.

Exactly, I think the percentage is higher than that

[Shyheels]

1 minute ago, pebblesf said:

Exactly, I think the percentage is higher than that

I agree. I’m quite sure there is a large latent desire out there to wear tall boots, with and without heels 

[bluejay]

I like to wear pink shoes and boots very much. Also pink clothing. I don't understand why men shouldn't wear pink. Even my 97 year old father-in-law wears pink shirts and pink ties but I've never seen him wearing pink shoes!

Happy Heeling,

bluejay

[Shyheels]

I remember getting comments on a pink Goretex parka I bought about thirty years ago. I coukdn’t have cared less. I liked the colour

[Puffer]

Pale pink shirts were quite often seen with a business suit and tie from the mid-60s, albeit sometimes frowned on by those supposedly running the show.  I certainly wore one (without adverse consequences) in my professional office and out to clients.