Boots and Skirts in Public

[Thighbootguy]

I thought I would start a new thread in this forum because, for me, wearing a skirt is a different subject than wearing boots or heels. This seem the appropriate forum.

In trying to put my thinking on paper I need to get a few definitions out of the way:

Women’s clothing - The male and female form a re normally different and clothing manufactures have created clothing to fit both of these forms. ie. men’s and women’s clothing

Fashion - What society (which is an average) will accept as proper clothing. This is often different for each gender. Men’s fashion is traditionally more conservative in style and color where women’s fashion is not kept within the same bounds.

I have wrestled with the question of am I a cross dresser and I think it depends on your definition. If cross dressing is

1. Trying to be mistaken for another gender

2. Wearing clothing that are fashioned to identify another gender (for whatever reason)

3. Wearing clothing you like without regard to fashion (fashion freestyling)

I think I fall somewhere between 2 and 3.

I have been wearing thigh boots with flat and stiletto heels for several years because I like the look. I have started wearing leather skirts because I like the look and feel of the material.

I’m sure I will come back to this topic in further posts.

This weekend I took a trip to Portsmouth Ohio to help a friend with some repairs. For the trip I wore a tan baseball cap, blue denim high wasted jacket cut with an open V front, white knit plain front shirt, brown suede mid calf length skirt, and black leather thigh boots with 5” stiletto heels. The outfit is a combination I enjoy and it doesn’t look bad either.

I made several stops on the way to Portsmouth. First I stopped at a large Goodwill (thrift store) that I don’t often get to. Again the hardest step was getting out of the car, but I decided I really did like the look so out I went.

I walked into the store expecting heads to turn but they didn’t. I guess most folks noticed what I was wearing, but some really didn’t. Everyone seemed to be willing to let me dress as I liked without comment. I really was expecting looks (from double takes to stares) and comments but I got nothing. I wandered around but didn’t see anything I wanted so I headed back out which meant a walk down the long wide isle that lead to the door. To get out I had to go through a crowded doorway and walk across the parking lot back to the car. By this time I had all the confidence I needed and the walk was uneventful.

Next I stopped at a Sam’s club that I had never been to before. I got one double take from a manager type when I walked in but that was the end of the reactions. I walked all around the store looking for my stuff (new store and I had to look). I did get an occasional glance but again most folks didn’t pay any attention. When I got the checkout I got into the longest line. The register clerk was a young lady and as I was paying I said, “This is my first time in this store. Is this too much?” I was standing so she could see the whole outfit.

She looked me over and said, “No, it looks cute. What’s the occasion?”

“Nothing special, I just like the look.”

We bid each other a good day.

Cute wasn’t the look I was going for but the comment was meant in the nicest way.

Next I stopped for gas at a pay at the pump station and no one notice what I was wearing.

When I got to Portsmouth I changed into jeans and flat heeled boots and pulled on a knit blue shirt and left the jacket in the car. My friend isn’t heels. We worked for a couple of hours and I headed back home.

We changed back into the thigh boots and skirt for the drive.

I stopped at Mjyers (Big grocery/department store) and picked up a few items then wandered around the store. I dot a little notice but very little. No one said a word or gave a second look.

When I got to the register I asked the clerk (young lady), “Is this too much?”

I got the generic, “Doesn’t bother me any”.

I pressed a little further, “If it wasn’t that a guy is wearing them, what do you think of the boots?”

And again I got the, “Doesn’t bother me any”.

I headed back out to the car and home.

I really enjoyed the trip and the look and I’m hoping to repeat it soon. Now I’m trying to figure out why I enjoyed it so much. I suspect there is a feminine side of me that is trying to get out. I know it is there and express itself when I paint or draw so expressing itself in my dress might not be too much of a next step.

[silver]

I think I've experianced the same feeling as you when I went into a shops in Vegas that catered for the TV scene. The shop assistants are used to that type of thing and I got comments that I really liked, like how sexy my feet looked in pumps and so on. What I'm saying is that it's nice to be able to live openly, without being rejected.

[Thighbootguy]

Here is an image (my apologies for the quality) of what the clerk thought was cute.

silver -

I don’t wear heeled boots and skirts anywhere near work. The folks there would not understand. But I am starting to enjoy wearing a skirt and thats the reason for this thread.

I would expect folks selling you something to complement you on how good you looked (and no doubt you do).

[kirkules]

I believe that we should be able to dress as we wish without fear of prejudice or ridicule. I enjoy wearing skirts and boots but feel exposed and unable to defend myself. The only time I went out properly in my nice black ankle boots with a stilleto heel, I clop-clopped around the Co-Op shop and drew every-ones attention. Still, onwards and upwards. I try to practice what I preach. Next month (June 06) I am going to have a full make-over at my local beauticians in Carterton in Oxfordshire. My eyebrows will be reshaped and I will have full make-up and I will dress en-femme from head-to-toe including a strawberry-blonde wig when I leave. I shall let you all know what, if any reactions I get and if they are good or bad.

[Thighbootguy]

Today I went to Bigg’s wearing a white top, blue denim jacket, black baseball cap, white hose, black leather thigh boots with 5” stilettos, and a brown suede mid thigh length leather skirt. Either folks around here are willing to accept a guy dressed like this of this is so far over the top that people don’t know what to do.

I was there earlier in the day than I normally am and there were employees that had never seen me in thigh boots before. I got a couple of looks as I walked across the parking lot and into the store. I had an item to return so I had to get into the service desk line. No one even seemed to notice how I was dressed and no one made any comment at all. I had lots of time so I wandered all over the store. One fellow was looking for an item and I pointed out where it was. He seemed glad for the help (even from a guy in a skirt and boots) thanked me.

When I got to the register the clerk was someone I had never seen before. I asked her how the outfit looked and got a non committal smile which meant she really didn’t approve.

As I was leaving the lady at the exit door said the outfit looked “Nice”. I knew she had banged up her knee several months ago and I asked her how it was doing. She was pleased that I remembered and we bid each other a good day.

When I got back to the car and loaded my stuff into it, I decided to go back in and price some tires. I walked back across the parking lot and back into the store. The greeter asked if I had forgotten something and I told her I wanted to look at the tires. I wandered through the rack of tires until I found my car’s size and noted the price.

On the way out, I asked the greeter, who I knew, how I looked. She also said it looked “Nice”. I asked, If it wasn’t a guy wearing this, how would you read it?”

She looked me over again and said, ‘I still think it looks nice. I like suede.”

We bid each other good day and I walked out and back to the car.

The next stop was Radio Shack. I parked and walked across the lot and into the store. The clerk (young lady) was a little taken aback but she asked me if she could help anyway. She started treating me like a regular customer when she found out I wanted to buy something. None of the other customers in ht store seemed to care about a guy in a shirt and thigh boots.

Next I went to the thrift emporium (large thrift store). This is in a shopping center that has a store with mirror windows. I parked so I would have to walk by that store. This outfit does look good. I went into the store and started looking at skirts. Folks moved their carts out of the way so I could see all the stock. No one looked twice or said a word. When I walked through the shoe area I saaw a pair of boots that looked interesting. I pulled them off the rack and they were 9 West knee boots marked 10 ½. This is a little small for me but you never know until you try then on. I went over to the bench and sat down and took off one of my thigh boots. I tried on one of the 9 West boots and it was a little tight but it did fit and the shaft fit my leg like a glove. These were now my boots. I still had to take the boot off and pull my thigh boot back on. Remember I’m wearing a reasonably short skirt so this operation was not the easiest thing to go. I’m sure I had an audience but I didn’t notice.

As I was walking to the register one lady gave me a quick look over. I asked, “Too much?”

She replied, “If it’s your thing, do it good” and gave me a nice smile that I returned.

When I got to the register I found that everything was 20% of today so the boots cost me $3.60 (no kidding 9 West boots for $3.60).

9 West boots

I asked the register clerk and the manager (they were together and I knew both of them), “If it wasn’t a guy wearing this, what would you think?”

Neither offered an opinion but the register clerk did say, “We see a lot of that in here”, meaning guys either buying or wearing women’s clothing. That comment explained a lot about the reaction I get in this store.

As I walked out of the store and down the sidewalk, I heard a wolf whistle behind me. Normally I ignore this but this time I turned and a and a young lady was hanging out of the store door and giving me a smile. I asked, “Really?”

She replied, “Oh Yeah!”

I walked back to the car in a good mood.

Next I went to the Art Museum but I wore shorts rather than a skirt so I’ll continue this on the Thigh Boots in Public thread.

kirkules -

Please don't go out and clop aroung, even in a full make-over. People will pick up on you discomfort and give you lots of negative feedback

Walking in heels takes practice, practice, and more practice. Don’t go out until you can walk with grace and confidence. It’s worth the effort to learn how to walk in them. The confidence you will project wil be returned as neutral to positive feedback.

[kirkules]

I enjoyed reading your story Thighbootguy and appreciated the good advice at the end. Put a smile on my face. I wore my knee length suede boots last night with a brown leather skirt. To help achieve a proper walk to go along with the nice clop of a high heel I squeezed the inside of my thighs together. This I found really helped with my posture and walking gait. I shall be trying it for real next month when I walk out in public en-femme after my make-over. I am a little nervous but very excited. My wife is helping to build up my confidence with nice comments such as "You have got to be kidding me!" and "Hey Coco! Your nose has fallen off!" She loves me, I can tell............

[silver]

Hey Thighbootguy, it's tru what you say about the store clerks complementing a person, but there's only 1 friend that knows I'm a TV and she never gave me good advice/comments except when I shaved my legs. kirkules: lol, I like you comment at the end, it was funny.

[Thighbootguy]

Tonight I went out for a walk wearing a sleeveless black shirt, black toreador jacket, long full black leather skirt, and my granny boots. The skirt came to the top of my boots.

The neighborhood is getting a little busier so I may have to do something differently, besides its getting too warm for a long leather skirt.

Nothing exciting happened. I just thought I’d post something saying I was still at it.

Kirkules -

Thanks for the kind words. I didn’t know if the advice was needed or would be taken as good intention. I think your term “clopping around” must be an overstatement.

Your wife sounds like one of a kind. I know many that would be giving advice by swinging a frying pan.

[kirkules]

As promised, I shall tell you how my day went yesterday, 2nd June, going out into public for the first time, proper after a makeover. My beautician gave me a wonderful two and a half hour experience. She manicured my nails and gave them a French Manicure. She reshaped my eyebrows again, this time though a little more feminine than usual, and she also coloured my eyelashes dark brown. I showed her the colour of my outfit, very autumnal with tan brown leather skirt, dark brown hippy style top, black two and a half inch knee boots, black hold-ups (hose?) and a strawberry blonde wig. Once my make over was done, I dressed into my outfit and my hairdresser then reshaped my wig for me. She feathered the front a little and gave it a good brush. It was now time for me to take that step out into the hussle and bussle of downtown Cartoontown in Oxfordshire, a very male orientated town served by a military air station. I was starting to feel very nervous. The palms of my hands started to sweat. My wife told me to be calm, walk tall and to walk on the line. This was it. The exit to the salon beckoned. Would people stop and stare at me? Would aircraft fall from the sky? Would the Seven Riders of the Apocalypse appear? I walked out into the sunshine with my sunglasses on and my head tall. Suddenly, five young lads about twelve years of age walked towards me. Would they realise that the tall Amazonian beauty walking towards them was actually a man? They didn't bat an eyelid. I walked around half the town, walking the line, head back, my heels clop-clopping. No one payed me any attention. I did it! I was a woman in society. My wife and I went to visit some friends after that. They had not met me dressed up as Kirsty. They were cool with it. We had a good laugh and they treated me like a lady, even giving me a new handbag. I drove home, a journey of sixty six miles. I felt really comfortable. I can only hope now that I can continue with this while in Germany. Onwards and upwards. Coco can have his nose back now.....!!

[sendra45]

Wow, I bet the town did not know what hit it! I am so very glad that it is all going well for you, Germany will be just as much fun. I was wondering if you could either post a pic of yourself as Kirsty (in heels of course) or if you are shy, email me one. I think I am the only one here that has met you, It means a great deal to me to know that you are addressing your desires and needs, there seems to be quite a few 'wanna be's' and here are you living the dream, good for you. Drinking cider in the sun is no good though, I have only just got the Coco Joke. I am going to have a sleep now. Nigel.

[sendra45]

I have the pleasure of introducing you all to Kirsty.

Thanks Kirkules.

Nigel

[Thighbootguy]

Kirkules -

Nigel understated it a bit, it’s more like

W O W.

What a great adventure and post. It must be wonderful to have the support of your wife and beautician (who, by the way, did a nice job).

Nigel -

Thanks for posting the picture.

[bobbi]

Kirkules, Thanks for sharing your story with us. Congratulations on your first time out on the town as Kirsty. You look great! Your beautician did a fine job. May Kirsty have many more adventures! bobbie

[kirkules]

Nigel, Thighbootguy and Bobbie, Thank you all for such kind remarks. I was really surprised to see Kirsty in all her glory and beauty in the mirror in front of me. So much so that last Saturday, while England thrashed poor Jamaica 6-0 at football (I didn't really watch, I am a Scotland supporter for my sins) I went and had both my ears pierced to add to the realism for Kirsty. I find clip-on earings hurt my ears too much. Thanks again guys, and thank you Nigel for posting my picture, I was having real problems getting them onto the net.

[shyguy]

Great job Kirkules, the whole look works perfectly, it's now wonder you were just accepted as a woman. Well done for finding the courage to go forward with it.

[Dawn HH]

Kirkules:-) No wonder no one took you for anything but a woman on your first outing. Your look fits so well together, thanks to your beautition and your wife. They were a great help to you to advise you and to help you put everything together. Keep us posted with stories and pics on any adventures that Kirsty may have in the future. Thanks for sharing. Cheers--- Dawn HH

[stefaniboots]

[Thighbootguy]

Today was hot and I started wearing shorts with a ½ inch inseam (very short) and a T shirt worn loose. Normally when I work in the yard I wear jeans and flat heeled thigh boots but it is far too warm to wear boots, especially thigh boots. I had a bunch of yard work to do which included cutting the grass. As I was working I noticed no one was paying any attention to a guy in shorts cutting the grass so I went in and changed into a black leather mini skirt and the same loose T shirt. The skirt was about as long as the shorts and I wore the T shirt loose over the skirt. This was a very comfortable outfit and you really had to look twice to notice what I was wearing (and no one did).

I’ve always thought this skirt was too short for me to wear in public but worn like this, under a shirt, I might get more use from it.

I really like the looks of this skirt worn as it should be, with the shirt tail inside the skirt so the full skirt (all that there is of it) is visible and worn with boots, either knee high or thigh high. This look, however, is just a little too much for me to present in public.

stefaniboots -

I wrote my post before I saw your picture. That is a great look. That skirt is about the same length as the one I was wearing today. I may have to rethink short skirt wearing.

Normally when I go out, I go out as a guy wearing a skirt and boots. I’m not sure I can pull it off in a mini skirt.

[Thighbootguy]

I have maintained that I can walk in a 5” heel with grace and comfort but tonight was an exception. The sun had gone down and it was cool enough to venture out in a leather skirt, black satin blouse, and black leather thigh boots. It was also dark enough to not attract too much attention. As I was walking up the street, my sciatic nerve started acting up again (this has been going on for several weeks now). This made it painful to walk no matter what I had on my feet. Neither the boots nor heels were the cause of the nerve acting up but is sure affected the way I walked in them. Normally I take a full enough stride that I let my heel hit the ground first then I let the sole hit the ground as I move forward. This time all I could do was let the heel and sole hit at the same time with a much shorter stride. I also notices I was weaving a bit. This was not my most graceful outing so I cut it short and headed back home. The pain quit as soon as I sat down. I may have to see the doctor about this. Can't have this weaving around in heels.

[crotchboots-m]

sorry to hear about that thighbootsguy...sure its not your hip,tho? when it acts up it has similar symptoms.

[Thighbootguy]

I really am starting to enjoy wearing a skirt. I went out for a walk tonight with a black baseball cap, long sleeved white shirt, black suede skirt and black “suede like” knee high boots. This is a very simple black and white outfit that (if I hold my stomach in) looks great. It is also very comfortable on these warm evenings.

I like the look but I’m still not comfortable meeting people on a dark street at night dressed in a skirt. I don’t have a problem going into a store in the daytime but you never know who is out walking the streets at night. I’m glad my own advice on not becoming complacent kicks in at times like this.

There were several people out tonight and I managed to avoid meeting them. I’m sure they saw me but it was dark enough to avoid details.

crotchboots-m

Thanks for the concern. I'm pretty sure its a lower back problem. It has bothered me on and off for as long as I can remember. One of the serious medical options that has been offered is, “live with it”. It seems to be getting better (or less worse).

[Dawn HH]

TBG:-) Sorry to hear about your pain problem. Best to see about it now and to find out just what is causing it. It could be caused by more than one thing and a check-up could pin-point the cause. Mickey and I have made an appointment for me with an arthritis clinic near here to get a good check-up and see what is going on with my joints. I have been having a lot of problems with them and my walk is getting quite eratic so therefore I haven't been able to streetheel for a while. To me, this is terrible and the pain in my knees and hips is getting worse by the day. I can't enjoy streetheeling right now, which is the worst pain of all. Cheers--- Dawn HH

[dr1819]

Cool - you're into skirts, now - sweet!

You'll find as you increase your world travels that skirts are the norm for men throughout many countries. See http://www.kiltmen.com/world.htm

While heels for guys is a bit unusual today, it's on the uprise, so give it time.

In the meantime, I wear heels and skirts around the house on a regular basis. In Germany we have no A/C, so the skirts keep me cool (just as they were intended thousands of years ago, alleles willing), and the heels are simply a personal preference as adopted by men on and off over the last 500 years throughout this region.

[micha]

Cool - you're into skirts, now - sweet!

You'll find as you increase your world travels that skirts are the norm for men throughout many countries. See http://www.kiltmen.com/world.htm

While heels for guys is a bit unusual today, it's on the uprise, so give it time.

In the meantime, I wear heels and skirts around the house on a regular basis. In Germany we have no A/C, so the skirts keep me cool (just as they were intended thousands of years ago, alleles willing), and the heels are simply a personal preference as adopted by men on and off over the last 500 years throughout this region.

Hi dr1819,

today the weather in Frankfurt was extremely sultry. Even if not engaged in skirt wearing I wore the whole day a short denim skirt. That's simply the most comfortable clothing at 35 Cel!

I hope we'll see us in Amsterdam

micha

@Thigbootguy: I have trained my turkish neighbours by stubborn indulgence Since weeks I havn't earned any bad comment from immigrants. For them I'm only still the queer big blond guy who is wearing high heels. No comments today on my skirt.

[Thighbootguy]

I was out in my white shirt, black suede skirt and black suede like knee boots again tonight. I’m still not 100% comfortable walking around the neighborhood in a skirt and boots. I still think the outfit looks great and it is very comfortable to wear but I’m still haunted by the phrase of my grandmother when I was growing up, “What will the neighbors think?” That feeling wouldn’t be so strong except for the fact that I’m now living in the same house I grew up in 50 years ago.

[Thighbootguy]

Ah once more around the neighborhood in boots and a black suede skirt. Tonight I wore a shiny black blouse with the black skirt and black boots. The contrast is that I’m not wearing hose and my legs show from below the knees to mid calf (short skirt). This outfit looks as good as the white shirt and is just as comfortable. I’m still not ready to meet the neighbors while wearing a skirt so I’m cautious about when and where I go. There is still a lot of drive by traffic and I haven’t noticed anyone paying any attention at all. I do enjoy this look. I’ll have to find somewhere to go out and about in my skirt.

[Stilletto2004]

The only time I've worn boots and a skirt in public is when I am Jennifer. I have worn skirts before, and boots under jeans in drab, but never the other way around. Hmm. Sounds like it could be fun.

[Thighbootguy]

I had a great time shopping this evening. I stopped at Sam’s Club with a long list, long enough that I needed a flatbed cart. I went in wearing a long sleeved blue dress shirt, a black baseball cap, black opaque hose, a black suede short skirt, and my white leather thigh boots with 5” stiletto heels.

I walked across the parking lot and into the store only to discover that there were no flatbed carts available so I walked back out and across the parking lot to get a cart. I was noticing that lots of folks paying attention to what I was wearing.

I finally got into the store and spent an hour wandering around getting my stuff. Several of the staff greeted me with a pleasant Hi.

When I got to the register area one of the clerks called me to her empty register. I had to help her with some of the heavier items so I was not just standing there while she rang things up. She didn’t seem to take any notice to what I was wearing. When she finished I asked, “Is this too much?, indicating the way I was dressed.

She replied, “Hey that freedom of speech. You can wear anything you want”

I must admit I hadn’t associated fashion freestyling with freedom of speech and while I was thinking about it she said, “but I like it though”.

I thanked her and headed out of the store. When I checked my receipt I realized she had run an item up twice so I headed to the service counter for a refund. I think the lady there had seen me wearing boots before but not a skirt. She treated me like all her customers wore thigh boots and leather skirts.

On the way out the clerk at the exit, who knew me well, asked, “Did they make a mistake again?” (this has happened before)

“Yeah, they rang up an item twice.”

“Well its good that you caught it.”

“I think its this outfit that causes a distraction”

We both laughed and bid each other a good evening.

Out in the parking lot it took a while for me to get all the stuff loaded into the car. Again lots of people seemed to notice what I was wearing but no one said a word.

Tonight I was out in the neighborhood wearing a gray short sleeved T shirt, black baseball cap, black suede short skirt, and dark blue (looks black) leather knee boots. I didn’t meet anyone but there was lots of traffic. The big event was that my sciatic nerve problem seems to be getting a little better.

This has been a fun day!

This mornings outting is posted on Thighboots in Public

Stilletto2004 -

I’m not quite sure what the “other way around” is boots and a skirt in drab, or boots over jeans. I highly recommend the boots over jeans look. I have been doing that for several years and it is still my favorite look (and I do it with thigh boots with stiletto heels).

[Stilletto2004]

What I was saying is that I have worn a skirt in public before, but not with boots. I've worn boots under jeans. Just never put the skirt with the boots - not sure I've got the nuts to pull that one off.

[Thighbootguy]

Stilletto2004 -

My strongest recommendation is to try boots over jeans. Keep the contrast low, black boots over dark jeans or white boots over white jeans. Contrast is really the thing that attracts attention. I really have gone places wearing black thigh boots over dark blue jeans and had no one notice (and the boots have 5” stiletto heels). I don’t mean the people were polite and didn’t say anything, they really didn’t notice. Sometimes, out of frustration, I have asked people what they thought of my boots and they honestly replied that they hadn't noticed.

As for boots and a skirt, the same concept applies, the less contrast the less attention. I have been wearing the black suede skirt with the black boots but with bare legs. I like the look but I have also worn black hose which takes the contrast to zero. On a dark evening you would have to look closely two or three times to notice the skirt.