Skirts: A Natural Progression From Heels?

[robbiehhw]

I am wearing more skirts and dresses as i transition further but truthfully i feel just as en femme in girl's pants and jeans. In winters i really do like the sweater dress, boots and tights combo though, i am doing that more this year.

[Sydheel]

Whilst i see and acknowledge that some are transitioning i dont believe it is a natural B follows A type of thing. 

Im not the prettiest of blokes and im sure id be further down the list as a girl. LOL

pity really cause it been so damn hot here would be great. !!

james

[Ynotme]

As you can see in some of my pics i have skirts but there for inside .Also I am a little over weight  not much but enough I would not look right out in a skirt

Thats ok is only my way

[Thighmax]

I don't really know if going for skirts is the natural progression.  From my experience, after I accepted my love for high heels, I started trying other "female" attire.  I tried hosiery, leggings and dresses.  I have gotten to the point in which I understand that I don't only like high heels, I like the clothing because it gives my way more chances to express myself.  For example, I love leather gloves, but I choose to wear plum, read, pink and other colors that would usually be considered female.  I have bought a few pairs of gloves and see that even though they come from the female part of the store, they don't necessarily look feminine, but the color does.  

I like to use bold colors, I like the way the look.  Skirts, from my point of view, are more comfortable because they give you more chances to move freely.  

[Lawrence]

You are so right.  I go for heels big time though I only have a few, but I progressed to skirts, dresses and all the undertiings as well.  Panties are much more comphy then tighty whities or boxers, thigh high stockings with garter and tights are way comfortable.  Not only that there is such a big selection of colors and styles.  I love them all.

[hh_pe]

I find women's clothing to be more comfortable than men's.  I guess my dressing transitioned from wanting to look like a woman (i.e. wigs, body contouring clothing, make-up, etc.)  to just a guy who enjoys women attire. Stretch jeans and yoga pants are the only female times I constantly wear now.  When appropriate, I will wear the jeans in public. The yoga pants and the one skirt I have are for home use only.

[Lawrence]

I am so with you there.  Womens clothes are so much more comphie, more colorful, and feel so good when I am in them.  I stay in girdle, tights and panties under my ( have to wear) mens stuff 24/7.

[Lawrence]

 

While I am not a pro in those 4, 5, and higher heels I absolutely love my 3" heels and find them so very much more comfortible then mens shoes.  I started wearing them for the sexy nature of men in heels but quickly came to love them just as shoes.  I underdress 24\7 so yes I wear hose with my heels.  I also wear the other undergarments as well.  Love the nice snug feel of them on me.  YES wearing dresses is absolutely the next step.  I love the open airey feeling of them as opposed to the constricting properties of pants.  You are so right there are so many styles, colors and paterns, and so many combinations.  Just a dress, and a blouse and skirt.  I often, when wearing a dress. wear under it a nice full petticoat.  It really brings the fem out in this heel wearing guy!!!  Hose also.  So many colers to chose from and now the patterned variety.  I love all of them.

[Chorlini]

I didn't want to open a separate topic for it but for the first time ever I saw a guy in a skirt today. Really short one too, with black patterned pantyhose and flat pair of boots. I originally thought it was a chunky girl as he had long hair then I passed by close and noticed facial hair. It's not something I would like to do myself but I admired his guts in doing so. Not the least because it was quite chilly.

[Lawrence]

2 hours ago, Chorlini said:

I didn't want to open a separate topic for it but for the first time ever I saw a guy in a skirt today. Really short one too, with black patterned pantyhose and flat pair of boots. I originally thought it was a chunky girl as he had long hair then I passed by close and noticed facial hair. It's not something I would like to do myself but I admired his guts in doing so. Not the least because it was quite chilly.

 

2 hours ago, Chorlini said:

I didn't want to open a separate topic for it but for the first time ever I saw a guy in a skirt today. Really short one too, with black patterned pantyhose and flat pair of boots. I originally thought it was a chunky girl as he had long hair then I passed by close and noticed facial hair. It's not something I would like to do myself but I admired his guts in doing so. Not the least because it was quite chilly.

while I am not a pro in those 4, 5, and higher heels I absolutely love my 3" heels and find them so very much more comfortible then mens shoes.  I started wearing them for the sexy nature of men in heels but quickly came to love them just as shoes.  I underdress 24\7 so yes I wear hose with my heels.  I also wear the other undergarments as well.  Love the nice snug feel of them on me.  YES wearing dresses is absolutely the next step.  I love the open airey feeling of them as opposed to the constricting properties of pants.  You are so right there are so many styles, colors and paterns, and so many combinations.  Just a dress, and a blouse and skirt.  I often, when wearing a dress. wear under it a nice full petticoat.  It really brings the fem out in this heel wearing guy!!!  Hose also.  So many colers to chose from and now the patterned variety.  I love all of them.

[Lawrence]

I sure wish I could have been there.  I'd have stopped and chatted a bit just to see where he was comming from.  Maybe sat down and had lunch with him and got to know him a bit.  For sure discussed our mutual dress preferences.  To bad the boots were flat.  Looks so much more aluring in heels.  Patterned hose wow he was brave!!  Just guessing by your discription it must have been a mini skirt?  Do you remember any of the colors of things he was wearing?  Did the outfit all match?  Just wondering.

[Chorlini]

6 hours ago, Lawrence said:

I sure wish I could have been there.  I'd have stopped and chatted a bit just to see where he was comming from.  Maybe sat down and had lunch with him and got to know him a bit.  For sure discussed our mutual dress preferences.  To bad the boots were flat.  Looks so much more aluring in heels.  Patterned hose wow he was brave!!  Just guessing by your discription it must have been a mini skirt?  Do you remember any of the colors of things he was wearing?  Did the outfit all match?  Just wondering.

All I remember was him wearing a tan coat that came to his hips, and panty hose all the way down there. So it must have been a mini skirt, otherwise he'd be really bold. I briefly considered talking to him and at least complimenting him for his bold choice. But I had to go back to work and you know how it goes, a million excuses not to do a thing.

[Curt]

On Wednesday, August 12, 2015 at 3:51 PM, Histiletto said:

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.

I think people should wear whatever they like. Our day would go a lot smoother if we are comfortable in the clothes we wear. 

 

I like dresses with heels and boots. If I wear a skirt,  I'll put a belt with a huge buckle with it. I find it makes my lower body a lot longer. 

 

I know how the guys feel. I have a pair of 70s mend platform shoes that I would like to wear,  but I might be shunned wearing men's shoes as a girl. I'll send a pic soon, they look really cool. 

[Lawrence]

18 hours ago, pumpcat said:

I think people should wear whatever they like. Our day would go a lot smoother if we are comfortable in the clothes we wear. 

 

I like dresses with heels and boots. If I wear a skirt,  I'll put a belt with a huge buckle with it. I find it makes my lower body a lot longer. 

 

I know how the guys feel. I have a pair of 70s mend platform shoes that I would like to wear,  but I might be shunned wearing men's shoes as a girl. I'll send a pic soon, they look really cool. 

You go girl and wear those shoes.  As a girl no one will say a thing you can bet on it.  I just wish it were the same for us men.  The looks and coments are often and not very pleasant.  I sure wish it didn't have to be that way.

[Curt]

1 hour ago, Lawrence said:

You go girl and wear those shoes.  As a girl no one will say a thing you can bet on it.  I just wish it were the same for us men.  The looks and coments are often and not very pleasant.  I sure wish it didn't have to be that way.

I know. I wad afraid of showing off the heels? So I would wear long bell bottoms to cover the heel. I felt bad about it because I wasn't being true to myself. Who cares what people think.  If you like heels, then rock them. 

[hhboots]

On 12/10/2015 at 11:41 PM, Sydheel said:

Whilst i see and acknowledge that some are transitioning i dont believe it is a natural B follows A type of thing. 

Im not the prettiest of blokes and im sure id be further down the list as a girl. LOL

pity really cause it been so damn hot here would be great. !!

james

I know James' post was from a few months ago, but this is exactly how I feel.  I think if I could pull it off, I would definitely wear skirts out with heels often.  I really like the look and comfort of skirts.  I do have the legs for skirts, but the upper body is where it all goes wrong.  Maybe if/when I ever get as thin as I would really like to be, I might attempt it.  But in my opinion, honestly, anyone (man or woman) with a waist larger than the hips, wearing a dress or skirt is not a good look.    

[Lawrence]

While I agree if your waist is larger then your hips it would look awful if you wore a skirt, it is still a matter of opinion and if you want to go ahead.  Myself, being only a bit lg in the waist and def. not larger then my hips look as good as a 70 yr old man can look in a skirt or dress.  And of course heels.  I prefer tights as well.  Not that my legs are that bad but just the airey feel of them is a sensation I love.

[Lawrence]

If you like heels and have the courage to wear them then for sure rock out in them.  Just go clicking down the way all you want.  Don't hide them under pant legs.  Show them off.  Thats what heells are supposed to do.

[Curt]

Well, I really like dresses. It's easier, just outgrow one thing on. So many women don't dress elegantly anymore, or men for that matter anymore. 

[Thighbootguy]

1 hour ago, pumpcat said:

Well, I really like dresses. It's easier, just outgrow one thing on. So many women don't dress elegantly anymore, or men for that matter anymore. 

 

Dresses may be easier, but a skirt and top can give more variations.  I have been attributing the lack on my seeing elegant dressing on the places that I frequent, as elegant dressing would not be appropriate.  However, lowering the bar a little, I don't see much "neat" or "coordinated" dressing either.  You and @JeffB put most of the folks I see to shame.  I do try but I really don't have a good eye for it.  I normally start with "what boots do I want to wear" and work my way up from there.

 

[JeffB]

11 hours ago, Thighbootguy said:

Dresses may be easier, but a skirt and top can give more variations.  I have been attributing the lack on my seeing elegant dressing on the places that I frequent, as elegant dressing would not be appropriate.  However, lowering the bar a little, I don't see much "neat" or "coordinated" dressing either.  You and @JeffB put most of the folks I see to shame.  I do try but I really don't have a good eye for it.  I normally start with "what boots do I want to wear" and work my way up from there.

 

Well, that's a bit of a bother for me as well since you rarely see people of either gender dress up, at least not on weekends, save for Sunday morning when people go to church. But, there is a sense ease and simplicity to wearing a dress since it's just one item, put it on, add and accessory or two and it's off to the races.

[robbiehhw]

On 7/23/2016 at 3:46 PM, JeffB said:

Well, that's a bit of a bother for me as well since you rarely see people of either gender dress up, at least not on weekends, save for Sunday morning when people go to church. But, there is a sense ease and simplicity to wearing a dress since it's just one item, put it on, add and accessory or two and it's off to the races.

Even in the rather casual northwest,i do see an exception to that and that is evening wear. In urban areas around clubs, bars, restaurants and other events you see people dressed pretty stylishly. I think it is true though as you say, that during the day on most weekends, you mainly see casual dress. Our area of the country has the lowest percentage of church goers per se (and those that do often go casual). so you don't see a lot people dressed for church in restaurants on Sunday afternoon as you do in some place such as Texas for instance.

[Danvan1600]

Although I don't heel much in public, I agree wearing heels has progressed to skirts and tights etc, it just feels so much more fitting and comfortable, a couple of pictures of a skirt and my 5.5 patent pumps  

[Henri1942]

I wear skirts and hosery with my heels on a weekly basis.  I travel weekly on Business and you can find me in the hotel lounge in skirt and heels.

Henri

[Chorlini]

On 25-7-2016 at 7:03 PM, robbiehhw said:

Even in the rather casual northwest,i do see an exception to that and that is evening wear. In urban areas around clubs, bars, restaurants and other events you see people dressed pretty stylishly. I think it is true though as you say, that during the day on most weekends, you mainly see casual dress. Our area of the country has the lowest percentage of church goers per se (and those that do often go casual). so you don't see a lot people dressed for church in restaurants on Sunday afternoon as you do in some place such as Texas for instance.

I live in a fairly big city with a big university and I rarely see anyone dress up for clubs, bars and restaurants. Most women wear trousers with flats even when they go out at night. And most of the ones I see still wearing heels are foreigners. Fashionwise the Dutch woman is basically a peasant and barely manages to dress better then the average Dutch man. They actually seem to think Uggs go really well with short skirts. *facepalm!*

 

[swedeheeler]

Well. Went to a relatives wedding last week where the dresscode were jacket. The problem was. It's just applied to us men. The womens just got away with a light summer dress so they keeped cool all day long while we had to sweat in our synthetic slacks.

The temperature was in it's mid 80's inside the little chapel where the ceremony was. Outside just 75f.

Those days i wish i had big guts for wearing something light like the gals had. But it hadn't been nice to steal the attention from the lucky couple.

 

[Rockbass19]

I actually find myself going in a different direction.  Instead of skirts, I have taken a liking to wearing leggings with my heels.  I like skirts, but I'm not a fan of wearing skirts with unshaven legs, but I also hate shaving my legs!

 

 

[Thighbootguy]

4 hours ago, Rockbass19 said:

I actually find myself going in a different direction.  Instead of skirts, I have taken a liking to wearing leggings with my heels.  I like skirts, but I'm not a fan of wearing skirts with unshaven legs, but I also hate shaving my legs!

I wear leggings with boots all the time and they are almost essential with a mini skirt.

[CAT]

1 hour ago, Thighbootguy said:

I wear leggings with boots all the time and they are almost essential with a mini skirt.

I find fishnets the essential with a miniskirt lol that's just me !!!

[Thighbootguy]

1 hour ago, CAT said:

I find fishnets the essential with a miniskirt lol that's just me !!!

To borrow on an old phrase, 'There are old heelers and there are bold heelers... and then there's @CAT"