Skirts: A Natural Progression From Heels?

[JeffB]

In case no one has noticed, a fair number of HHPlace members like myself, Thighbootguy and others have migrated from wearing pants and jeans with their heels to skirts, and I find that a curious sort of development. When I first wore a skirt in public back in late summer of 2008, it was simply a lark then, a desire what I would look like, and when I decided that I did like my appearance, I started wearing skirts more and more, leading to the point where I'm wearing them full-time on my public outings today.

 

Time for an admission: I suspect that if I hadn't made that migration to skirts, I might well have lost interest in heeling. In terms of fashion, jeans and pants are rather limiting, boring even, but with skirts, the variety is nearly infinite: from minis to maxis and everything inbetween; denim, leather, wool and other fabrics; A-lines, straights, pencils and pleats, not to mention all sorts of solid colors and patterns, the sky is literally the limit. It's great fun for me to spend quality time pairing skirts with tops, hosiery and shoes to put together outfits, and the combinations when it comes to fashion are legion compared to pants and jeans. Having fully committed myself to being the most fashionable freestyler I can be, having the sort of options skirts gives me are important. A long time ago, I said that just wearing heels were no longer enough for me, it's the whole package from head to toe or not at all.

 

So, to others here who've migrated to wearing skirts, either in public or at home, what was your motivation? What drew you to them, what do you like about wearing skirts? And do you think that it's a common or natural thing for some heelers to progress to wearing skirts? I'd love to hear your opinions.

[Thighbootguy]

JeffB -

 

Back in 2008 I posted this thread about a Guy's progress in heels (now locked).  It still seems relevant today.  Everyone progresses at their own speed and stops on the path where they are happy.

 

I think I find wearing skirts as much an expression of my feminine side as it is a counter culture fashion statement.  Regardless of which statement, skirts are a fun and comfortable garment to wear.

 

TBG

[Michou]

JeffB -

 

Back in 2008 I posted this thread about a Guy's progress in heels (now locked).  It still seems relevant today.  Everyone progresses at their own speed and stops on the path where they are happy.

 

I think I find wearing skirts as much an expression of my feminine side as it is a counter culture fashion statement.  Regardless of which statement, skirts are a fun and comfortable garment to wear.

 

TBG

 

Considering fun and comfort, the next best step I took, some 5 years ago, have been to wear dresses. Ok! The first few days, without wearing wig and makeup, I felt I might be pushing the envelope a bit too far. But a few compliments on the long strapless dresses I wore made me much more at ease. So much so that, last summer, I started to wear false boobs because that broaden the choice of dresses I enjoyed wearing.

[robbiehhw]

I think we often do the progression as we dress en femme. Mine started in my late teens and continues 30 yrs later. I own almost know male clothing and i'm on the transition path now. Skirts and dresses i wear less than jeans, pants and shorts but i do wear them.

[Histiletto]

My desire for stiletto heels will keep me wearing them even after my mortal demise, as far as I am concerned. This idea that we are wearing gender labeled items is part of our social brain-washing. The item(s) of apparel that strike your fancy and you find them pleasing to have on, are outward expressions of who you are. This is the natural aesthetic properties of what attiring is suppose to accomplish. Using clothing to classify or segregate people is a demeaning habit society has developed to promote its man-made ideals for caste or role playing type systems. So wear the fancies of your desire that you are pleased with having on for the intended occasion.

[JeffB]

JeffB -

 

Back in 2008 I posted this thread about a Guy's progress in heels (now locked).  It still seems relevant today.  Everyone progresses at their own speed and stops on the path where they are happy.

 

I think I find wearing skirts as much an expression of my feminine side as it is a counter culture fashion statement.  Regardless of which statement, skirts are a fun and comfortable garment to wear.

 

TBG

 

Wow! That essay of yours was right on target, TBG! Everything you wrote about resonated with me to perfection, and while my personal path stopped at "Wearing outer garments in public with confidence", that's more than good enough for me, that's where I want to be in my journey as a fashion freestyler.

 

My desire for stiletto heels will keep me wearing them even after my mortal demise, as far as I am concerned. This idea that we are wearing gender labeled items is part of our social brain-washing. The item(s) of apparel that strike your fancy and you find them pleasing to have on, are outward expressions of who you are. This is the natural aesthetic properties of what attiring is suppose to accomplish. Using clothing to classify or segregate people is a demeaning habit society has developed to promote its man-made ideals for caste or role playing type systems. So wear the fancies of your desire that you are pleased with having on for the intended occasion.

 

Well said, Histiletto! Well said! I couldn't agree more! Thanks for your comments, everyone!

[Thighbootguy]

At the end of my 2008 post I included a caution that is worth repeating:

 

One nice thing about this path is that you are the only one making you walk it. (A word of caution, don’t let your posting about your adventures push you along. Proceed at you own pace and only as far as you want to go.)

 

 

Let me add that you shouldn't let anyone else push you along the path.   JeffB and I good naturedly banter back and forth about thigh boots and skirts/dresses, but I think JeffB would have discovered thigh boots, and I would have discovered skirts/dresses, without each other's encouragement, it just might have taken a little longer.  The point is neither of us pushed the other one into something, rather, we just pointed out something we enjoyed.

 

Stop and go at your own pace.  Don't go too fast, this is a nice stroll, not a race.  At times it may seem like a sprint,  but a marathon is a better analogy.   Enjoy the journey.

 

Since I made the original post, peoples attitudes have become more tolerant of folks on the path but, the path is full of bumps and depressions (that may seem like mountains and crevasses),and twists and turns; you may take three steps forward and two backward, but it is a hard path from which to exit.

[Thighbootguy]

I found an interesting guide on ebay

 

How to wear Boots with Dresses and Skirts

[JeffB]

I found an interesting guide on ebay

 

How to wear Boots with Dresses and Skirts

 

Yes, that was an interesting, and informative piece. thanks for sharing!

[NrthEastHeel]

I always enjoy wearing skirts and dresses, with stockings ofcourse. With heels, and the entire ensemble it feels more complete, and very comfortable.

[mtnsofheels]

Hi Jeff, 

Interesting observation and question. I certainly feel empowered by getting past the first heeling days and now have more confidence to wear what interests me, and now hosiery under shorts, skirts and unikilts are happening too. I think once someone gets by those initial fears and sees yes you can wear non traditional items and be safe there is much to explore. It does make me look at more items and think...could that work for me?   Sky is the limit..

To answer your question directly, does wearing heels make skirt wearing a natural progression? I think it allows us to expand to whatever we feel is a traditional ladies wear item and be more accessible males to wear. I wore corsets for many years before heels, then hosiery, heels and now skirts. An individuals journey to freestyle wearing.

[redandwhite]

Not sure about a natural progression but knee high boots deserve to be shown off and not hidden under jeans or trousers!

[LuvyourShoes]

My desire for stiletto heels will keep me wearing them even after my mortal demise, as far as I am concerned. This idea that we are wearing gender labeled items is part of our social brain-washing. The item(s) of apparel that strike your fancy and you find them pleasing to have on, are outward expressions of who you are. This is the natural aesthetic properties of what attiring is suppose to accomplish. Using clothing to classify or segregate people is a demeaning habit society has developed to promote its man-made ideals for caste or role playing type systems. So wear the fancies of your desire that you are pleased with having on for the intended occasion.

This statement... excellent.

[JeffB]

Hi Jeff, 

Interesting observation and question. I certainly feel empowered by getting past the first heeling days and now have more confidence to wear what interests me, and now hosiery under shorts, skirts and unikilts are happening too. I think once someone gets by those initial fears and sees yes you can wear non traditional items and be safe there is much to explore. It does make me look at more items and think...could that work for me?   Sky is the limit..

To answer your question directly, does wearing heels make skirt wearing a natural progression? I think it allows us to expand to whatever we feel is a traditional ladies wear item and be more accessible males to wear. I wore corsets for many years before heels, then hosiery, heels and now skirts. An individuals journey to freestyle wearing.

 

Well said, my friend. I appreciate your well thought out comments.

[Histiletto]

As I understand mankind's beginnings, large leaves were the first coverings to be worn by those participants. I doubt they were concerned with more than the coverage, keeping them in place, and finding replacements when needed. It would seem the next item of need would be for the protection of their feet in spite of their developed callusing. Walking could be somewhat of an annoyance if they were to stroll upon jagged objects or thorny vegetation. Not sure if they had to worry about seasonal changes right off, but they were probably happy when they found something to cover with that kept them comfortable when they left the coziness of their dwelling.

The variety of coverings were simple, few, and most likely no difference in style or color. There were no rules or precedence as to what a person could cover with. These matters came much later when the population grew and individuals became more concerned about what was theirs and wanting to preserve some uniqueness in their appearance. Then the matter of possessions turned into class distinctions, which led to the limitations of appareling choices. The mess that has evolved since then has unjustly infringed upon every individual's right to choose their own appearance. As the selections became more numerous and improved, so did differentiation in caste type systems. Social rules and laws for attiring were created to separate people by their social importance and position, which helped to increase the distinction between men and women as well as families, communities, and regions. The result of these infringements have given the power of control to others over what was originally an individual's right to choose their own appearance. The simple covering of large leaves has been greatly improved and increased to many options of appareling items, but they are still coverings that come with the natural freedom to be chosen by any individual who desires to wear them. Obviously the fit, cost, and material compatibility has to be considered as factors as to who can wear them. However, when these limitations are satisfied, the final selection to wear them is the prerogative of the individual. If only the attitude of people weren't so narrow-minded by their social programming that supports society's usurpation of our individual right to choose the apparel we want to wear, this comment would not have been necessary at all.

[HappyinHeels]

AStutely said, as always, O Shakespearean One. Whilst this is a good read as it relates to the men I remember two girls that helped me a few ago at the new Steve Madden store in Gurnee, IL. Both had checkered pattern flannel shirts on and capri pants with flat sandals. Their hair and makeup were both superb but both definitely had mens shirts on. Women and girls simply do whatever the heel they want irrespective of the aforementioned societal limitations that seem to still aply to the men. It is up to us as to how fast and how widely we want to embrace the same fashion freedom the women are enjoying. Based upon all of the evidence I have seen offered here through sharing of experiences I would say most members could enjoy more fashion freedom since the only barriers are the mental ones we erect in front of us. I believe the real driver of the perceived limitation is the lack of a companion. So many of us are sort of independent operators and only occasionally have the chance to share the experience with someone else which helps unleash the creativity and the fashion freedom experience can truly be enjoyed. I would highly recommend everyone here to try to meet some other member in your travels. It does require time and attention to detail however. Just look at the great trip that LuvYourShoes just had in Seattle as proof.    HappyinHeels

[Steve63130]

Or look at the visits HinH has had to Ohio to visit us. What outstanding hosts he had! LOL

 

Humbly yours,

 

Steve

[hh4evr1]

Skirts are not a natural progression from wearing high heels for everyone. I have no interest in wearing any other items of "ladies" clothing.

I respect others choice to wear anything they like though.

[Steve63130]

Same here. Skirts are not my area of interest, which is a good thing, as my wife is definitely against me wearing one. We both are ok with heeling friends of ours who do like to wear skirts, though, even in our home.

 

Steve

[geezyweezy]

This leads down a different path. Be prepared if you do this...

[mlroseplant]

No desire to wear skirts here, either, even as my shoes become gradually more feminine as the years go by. What I do love, however, is shorts. Short shorts.

[HappyinHeels]

I'll vouch for the great hosts in Ohio;  I made sure my diction was smooth, my posture perfect, and heels towering as I was in the company of the Town's Vice Mayor and an innkeeper who wears the costume of a hosiery salesman. Or is it the other way around? Either way a great place and a great couple!!  HappyinHeels

[Oxford1]

It was my understanding that non shoe related topics were not supposed to be posted here. Past posts on skirts were moved to other topic areas. Please in force the rules fairly.

[Heelster]

It was my understanding that non shoe related topics were not supposed to be posted here. Past posts on skirts were moved to other topic areas. Please in force the rules fairly.

 

The title is one where the topic of heels would tend to lead a wearer to move on toward skirts - - I'm thinking it's fine where it is.

[hh_pe]

For me, it was the opposite, the skirts progressed to the heels. I was a crossdresser at one time and really enjoyed dresses and skirts, but never got heels to go with the outfits. It was my wife (girl friend at the time) who purchased a pair of heels for me to complete the look.

[robbiehhw]

hh - like you girl clothes proceeded shoes. For a long time i had only women's jeans/khakis and maybe 1 skirt (this was like 20+ yrs ago). I think somewhere in there the femme clothes sent me in the direction of getting shoes that went with the outfit. I don't recall the exact progression but i was something like that.

[Lime15]

I've actually really gotten away from skirts myself over the past year or so.  Really I keep them around for more of intimate type play with my SO, which she can really be up for from time to time.  Can't say why I moved away from wearing skirts frequently or as daily wear, the desire just went away - kind of how the desire to wear heels began before that.  For me though, yes, it was a forward step from heels to heels and skirts as a way to better pair regular dress with more exotic shoes.  Hosiery is the one thing that I don't see going away as in the cooler months I wear pantyhose with jeans and sneakers almost every day.  Even my shoe assortment has really been reduced over the past year, now concentrating on a functional group of eight or so pairs with only a couple of the crazy costume type "just for fun" pairs.  No reason behind any of that, the desire just changed over time.

[bss]

No Skirts here!  I've wore high heels for over 20 years.  I have not put on a skirt in my life and I don't think I will.... but I have used hosiery, so the high heels slip on easier and prevents blisters on a Walk a Mile is Her Shoes.  As for me, it is just high heels and maybe some hosiery.

[northshoreguy1981]

It started with heels/boots for me but in recent years I have progressed to skinny jeans, skirts, hosiery, corsets, jackets.

Sometimes I just feel like wearing a favourite pair of heels and other times I'll go for an outfit depending on my mood.

Haven't done anything above the shoulders though (i.e. wig, makeup) but that could be a next step.

[tightlevisandhhboots]

As I type this reply, I look back on the 30 years of fashion that I have been a part of, and heeling began with a great pair of Cowboy boots that fit really great! But on the other hand I started wearing kilts after a tour in Scotland courtesy of Uncle Sam. I do not mix the two currently or previously. I have toyed with dressing, but only at Halloween. I have decided personally that I will kilt and utilikilt as a guy, and I will heel as a guy, but to dress enfemme, that is not who I am. But I agree with other poster's that in my opinion, jeans are jeans, shirts are shirts etc, and as it works out I am lanky enough that women's jeans fit much better than men's jeans, so that is what I wear all the time, and have for many years.

TLAHHB's