Boots and Skirts in Public

[Thighbootguy]

I stopped at Sam’s tonight wearing a black sleeveless turtleneck, black short suede skirt, black leather thigh boots with 5” stilettos, and a gold necklace. Kind of hard to go wrong with black and gold. I should have worn hose to finish the outfit but I wasn’t able to manage it.

I walked in from the car and made sure I shortened my stride and pulled my shoulders back. (I’m finding that the stooped shoulder posture is something I have fallen into over the years and am going to have to work on it.) The greeter at the door recognized me and, to the amazement of the others around her, greeted me with a big hello and a very nice smile.

I didn’t have a lot of time this evening so I picked up the stuff I needed and headed for the register. My favorite register clerk was working and I asked her if the chain helped?

She replied, “Doesn’t hurt’”

That was not the enthusiastic response I was hoping for. I did ask a favor of her. I said, “If you see me wearing something really awful, and I don’t ask you about it, please tell me.”

I got a big smile and she said she would be glad to.

A digression

This lady has seen me in Sam’s at least once a week for a couple of years and when she is on duty I try to use her register. She is the first person I ever asked if my wearing thigh boots was too much. She said, “Doesn’t bother me none.” She was the first person that told me she didn’t if I wore thigh boots or not. To me wearing boots was a BIG deal and I thought it would be a BIG deal to others, but, to her I was just another customer (a little odd maybe, but just another customer). She does know me by name without looking at my membership card and I have often asked her advice. It's good to have someone to be able to talk to.

[Dawn HH]

TBG:-) It sounds like if you stick with that same check-out lady that knows you well you won't go awry and maybe she can steer you more right than wrong. Cheers--- Dawn HH

[Thighbootguy]

I stopped at Sam’s tonight wearing a long sleeved white shirt, a rust suede skirt and black leather thigh boots with 5” stilettos. I was not wearing hose because I made the mistake of grabbing the wrong skirt this morning. I was after a longer red suede one and in my hurry, got a shorter rust one. I didn’t discover my error until I was changing my jeans for the skirt after work. At Sam’s , still mindful to take small steps and keep my shoulders back, I walked in and was warmly greeted by the lady at the entrance, again, to the surprise of co-workers that were standing around her. I didn’t have a lot of time so I just selected the items I had on my list. I did notice a few ladies glance at me then down to my boots, but no one said anything. I know most of you really don’t believe me, but to everyone else in the store, I really am just another shopper. At the register, I got my favorite clerk and she didn’t mention anything, good or bad. I headed out to the car with my items, one of which was a 50 lb. bag of potting soil, and the clerk in the lot who was collection carts, asked me if I needed help getting it into the car. I thanked him but declined his offer. I did, however, think is was kind of neat that this guy would offer to help another guy who was dressed in a skirt and thigh boots. The stereotypical image would be for the clerk to avoid talking to that weird guy at all costs. I was pleasantly surprised.

[JeffB]

I stopped at Sam’s tonight wearing a long sleeved white shirt, a rust suede skirt and black leather thigh boots with 5” stilettos. I was not wearing hose because I made the mistake of grabbing the wrong skirt this morning. I was after a longer red suede one and in my hurry, got a shorter rust one. I didn’t discover my error until I was changing my jeans for the skirt after work.

No one's perfect. Still, your outfit looked well put together, even without hosiery.

I headed out to the car with my items, one of which was a 50 lb. bag of potting soil, and the clerk in the lot who was collection carts, asked me if I needed help getting it into the car. I thanked him but declined his offer. I did, however, think is was kind of neat that this guy would offer to help another guy who was dressed in a skirt and thigh boots. The stereotypical image would be for the clerk to avoid talking to that weird guy at all costs. I was pleasantly surprised.

You should've taken the clerk up on the offer. Hefting fifty pounds worth of anything is a pain, even in flat shoes, and believe me, I did more than plenty of that back in my Navy days. Next time, let others do the heavy lifting when they offer to do so. Heh!

[Dawn HH]

Go TBG, Go!!! I agree with jeffb. I would have taken that fellow up on hefting the 50lb bag for me. I can't lift more than 10lb at the present time, and believe me I have had plenty of assistance lately, which I really appreciate. And thats not in heels. Cheers--- Dawn HH

[Thighbootguy]

I had an interesting outing. I managed to pick out the red suede skirt this morning so after work I changed from slacks to the skirt with a white long sleeved shirt and black leather thigh boots with 5” stilettos. I headed for a Sam’s I don’t often use. The greeter seemed surprised when I walked in but recovered quickly. For the most part nobody paid any attention to me. Maybe it was the cart but very few people realized there was a guy walking around in a red skirt and boots, and if they just caught a glance, they would have registered female and let it pass. At the checkout I got into a line with a young female register clerk. The folks (man and wife) in front of me didn’t say anything but I think the guy went back and took a cell phone picture. I was sure the clerk had seen what I was wearing so after she had rung up all the items I moved to where she could see me fully and said, “you know, a lot of folks don’t even notice.” She gave me a puzzled look and then looked down and the look changed to surprise and she said, “and the reason is?” “I just like to wear them.” I got a nice smile and a thumbs up. In the parking lot, I was putting my stuff in my car when the guy that was in front of me in the checkout line pulled up and said, “Can I ask you a personal question?” “Sure.” “Do you always dress like that?” No, not all the time, but as often as I can.” We bid each other a good afternoon. On the way home I stopped at a gas station. This was a pay at the pump station so I got out and operated the pump. Again, no one batted an eye. I figure it must have been the red skirt. Next 4th of July, I’ll wear it and the white shirt with my blue thigh boots.

[highestheels]

What a nice story. Wow i wish the people in my neck of the woods were as tolerent!

[Thighbootguy]

I stopped at the Goodwill this afternoon an bought an olive cotton long sleeved blouse that had a vine pattern as a decoration. I thought it would look good with the red suede skirt, black hose and black leather thigh boots with 5” stilettos. That is the outfit I wore when I stopped at Sam’s on the way home. From the reflections I saw, the outfit looked good.

I wasn’t in a hurry so I wandered around in the store looking at this and that. No one seemed to notice or mind how I was dressed.

When I got to the register I got a clerk I liked and, after she had rung up my stuff, I asked her if the top worked. She said, ”Is it new?”

“Yep.”

“I like it.”

We bid each other a good evening and I headed out to the car.

Highestheel-

Living in a tolerant part of the world is part of it, (but I never expected Cincinnati to qualify as that) but projecting confidence is also a big part of it.

[highestheels]

Yes a agree it is the confidence that I struggle with as i know I can handle the 5 inch boots its just the public that worry me!

[maninkirt]

Well done Tighbootguy! And nice looking outfit too. The skirt, the blouse, the hose, the boots sounded right to me. Thighbootguy yes isn´t it just lovly not being in a hurry just wandering around in the store and in the shops looking and sometimes buying something too. I´m the same you know. Nice you had the chance doing a bit of talking with the lady at the register. Since me started dressing as a woman I noticed women are more open. I founded more easy talking to women. I don´t know how it is for you but women thinks more the way I do and I think more and more the way women do. GOOD LUCK Thighbootguy

[WA10rHeelGuy]

My local pub + Skirt + High Heels - Me = something wrong there. Just the weekend I leave St Helens and end up in Blackpool another Heeler is seen in my pub and he was even in a skirt (braver than me). Other than the drunken Neanderthal airheads it looks that St Helens, Merseyside is the new non-city home for heelers. Okay so 2 guys doesn't really add up to that but it's definitely a good start.

[highestheels]

Certainly is. Maybe he has been in before and you have inspired him!

[Thighbootguy]

I stopped at Sam’s last night wearing a green blouse with vine decorations, a black suede skirt and my black leather thigh boots with 5” stilettos. As I walked in I caught the eye of one of my favorite cashiers and she gave me a friendly wave. I only needed a few things so I didn’t dawdle around too much. When I got to the register of my favorite cashier, I asked her what she would do differently with my outfit. She looked me over and said, I wouldn’t change a thing, but then I don’t dress up very much so I’m not a good person to ask.” It hadn’t occurred to me that I was dressed up. I thanked her for the feedback and headed out to my car. Tonight I stopped in Bigg’s wearing a long sleeved white shirt and jeans with my thigh boots. No one seemed to pay any attention. Just another guy in thigh boots. I also stopped in my favorite thrift emporium and found a long tan suede straight skirt that has a long slit up the back. This skirt feels great to walk in. I think this skirt was designed as ankle length but I’m a little taller than the designers had in mind for the wearer to be so it hits just above my ankles, but it will look great with boots.

[JeffB]

I stopped at Sam’s last night wearing a green blouse with vine decorations, a black suede skirt and my black leather thigh boots with 5” stilettos. As I walked in I caught the eye of one of my favorite cashiers and she gave me a friendly wave. I only needed a few things so I didn’t dawdle around too much. When I got to the register of my favorite cashier, I asked her what she would do differently with my outfit.

Spent a couple of minutes painting a mental picture of the outfit you wore, and was pleased with what I saw in my mind's eye. You did well there as you coordinated your outfit well with your boots. It's clear you're developing quite a fine sense of style, and that you're not afraid to show it off to the world at large. Again, I greatly admire you for boldly wearing skirts and heels in public, something I'm eager to do but don't have the courage to. Yet. As usual, more power to you, my friend.

[Thighbootguy]

I went shopping at Sam’s tonight wearing a white long sleeved dress shirt, a black suede long skirt, and black leather thigh boots with 5” stilettos. The skirt was about mid calf so I wore my boots cuffed down to knee high. I wandered about a bit and no one seemed to notice what I was wearing. At the register I had one of my favorite clerks and she said she liked the look of the longer skirt. On the way out, my favorite clerk was tending the door and she also said she liked the longer skirt. Sigh... I wore that longer skirt because I thought they might like it but the problem is I like the shorter ones because the show off my boots. I guess it comes down to what image do I want to present, a guy in thigh boots or a guy in a skirt. I think, much to my two friends disappointment, it’s going to be a guy in thigh boots.

[JeffB]

I went shopping at Sam’s tonight wearing a white long sleeved dress shirt, a black suede long skirt, and black leather thigh boots with 5” stilettos. The skirt was about mid calf so I wore my boots cuffed down to knee high.

I wandered about a bit and no one seemed to notice what I was wearing. At the register I had one of my favorite clerks and she said she liked the look of the longer skirt. On the way out, my favorite clerk was tending the door and she also said she liked the longer skirt. Sigh... I wore that longer skirt because I thought they might like it but the problem is I like the shorter ones because the show off my boots.

I guess it comes down to what image do I want to present, a guy in thigh boots or a guy in a skirt. I think, much to my two friends disappointment, it’s going to be a guy in thigh boots.

Sounds like yet another interesting little outing. As I've said more times than I can count, I envy you for going out in a skirt and boots, something I long to do but haven't gotten up the nerve---yet. As for what image you want to present, why not do both?

[Thighbootguy]

I stopped at Walgreen’s and Sam’s last night wearing a long sleeved dress shirt, an ankle length tan suede skirt and black leather knee high boots with 2” block heels. These are the same boots I wear at work under slacks so there not too flashy. In both stores a few heads turned but that is to be expected. No one said a thing. This outfit says a lot more about a guy wearing a skirt than a guy wearing boots. The wearing boots statement is one I’m very comfortable making. I’m still working on the wearing a skirt statement.

[JeffB]

I stopped at Walgreen’s and Sam’s last night wearing a long sleeved dress shirt, an ankle length tan suede skirt and black leather knee high boots with 2” block heels. These are the same boots I wear at work under slacks so there not too flashy.

In both stores a few heads turned but that is to be expected. No one said a thing.

This outfit says a lot more about a guy wearing a skirt than a guy wearing boots. The wearing boots statement is one I’m very comfortable making. I’m still working on the wearing a skirt statement.

What a curious, and interesting statement to have made. Seeing how you've worn far shorter skirts in past outings, I would have thought you already reached your comfort level and that wearing ankle length skirts would be a cinch since, in a way, you wouldn't stand out so much. At the risk of being nosy (and please tell me if I am), I'd like to learn more about your thought processes in this area if possible.

[Thighbootguy]

This outfit says a lot more about a guy wearing a skirt than a guy wearing boots. The wearing boots statement is one I’m very comfortable making. I’m still working on the wearing a skirt statement.

Jeff;

Thanks for the question. Sometimes writing about things helps to clarify my thinking.

There is a lot bubbling under the surface in my comment. Here is some of it in no particular order.

• I have been wearing thigh boots with 4-5” heels for so long now that, very often (to me), they are just another pair of shoes. If there the only “out of the norm” item I’m wearing, I don’t give them a second thought. They still draw some attention when worn with jeans and a dress shirt but I’m totally comfortable and don’t give that outfit a second thought.

• As I commented to Richie, I still think skirts fall into the category of cross dressing so when I’m wearing one I have a different mental image of what I am projection then I do when I’m wearing jeans or shorts. Wearing a skirt causes a mental shift of gears that allows me to be comfortable doing it.

• With the exception of my thigh boots, the mix of clothing I choose swings between totally male and totally female (or between normal dressing and cross dressing) and most likely lands somewhere in between. Sometimes it’s jeans/shorts and a T-shirt/dress shirt, other times its a skirt/skort and blouse/sleeveless turtleneck with hose.

• I enjoy all these looks and haven’t made a decision on which one I enjoy most. I’m not sure I can because it seems to change from day to day. Some days there is no desire to wear even my boots, and others it’s boots and a skirt.

• Some days my beard doesn’t grow at all other days it’s a mess by the end of the day.

• I don’t attempt to pass as female. I’m going out a s a guy in non traditional attire. Someday I may experiment with makup and a wig but that’s is off in the future somewhere.

• I had an uncle who said that he wore an 8 but a 9 felt so good he bought a 10. I’m not an alcoholic but I enjoy one drink enough that the second one leads to the third (at which point I pass out). If a knee length skirt looks good and a short one looks better, then why not wear a mini.

Sorry for the ramble. Feel free to make any sense out of it you care to.

[JeffB]

TBG: No, you didn't ramble at all. I understood what you were trying to get across quite well. In fact, the coincidence regarding this topic is extraordinary since I just went out in a skirt for the very first time today. You can read about it here:

http://www.hhplace.org/discuss/general_fashion/11638-first_time_out_skirt.html

I can grasp how you would consider wearing a skirt more of an instance of crossdressing than wearing thigh boots, especially since you've done the latter a lot longer than the former and are more comfortable with that way of thinking. Some migt think that our wearing high heels also qualifies as crossdressing, but that's a narrow viewpoint that's already been discussed here ad nauseum.

So, what I've gathered from what you've said that you're still growing into your overall comfort level when it comes to wearing a skirt, thus your need to shift those mental gears which you've mentioned. As long as you enjoy what you wear, then continue doing what you love, however you choose to indulge in your passion. Bottom line: to each their own, you have to go your own way.

For whatever it's worth, I'm miles away from thinking about wearing a mini in public, as a matter of fact, I'd be more inclined to go the other way and wear longer skirts. Heh!

[Thighbootguy]

Tonight I stopped at Sam’s wearing a black sleeveless turtleneck, a red suede skirt, and my black leather thigh boots with 5” stilettos. The skirt is 20” s long, so the hem falls right at the top of my boots. It is a straight skirt (no flare) that fits tightly. The outfit is basically black and red so it is kind of hard to mess that up.

As I was driving to Sam’s there were black clouds in the sky and when I pulled into the parking lot, the sky opened and the heavens poured forth. This was a teal thunder splat but I figured I wasn’t going to melt so I put my baseball cap on my head (the theory is, if my glasses don’t get wet, it isn’t raining) got out of my car and ran into the store. Get the picture, 5” heeled thigh boots and a tight red leather skirt, running in the rain. I haven’t had to do that before and I’m not sure I want to do it again. When I got into the store I took off my cap, refastened the waist snap on the skirt, pulled my shoulders back, my stomach in, and started taking small steps.

I had time to shop tonight so I wandered all over the store. No one seemed to be bothered by or care about how I was dressed so I just took my time and enjoyed myself.

There is usually a cadre of older ladies giving out free samples of featured food products. I walked by one lady and I’m not sure if she wanted to speak to me or not but she finally said, “Hon, do you want to try some of this?”

I thanked her and declined. That was the first time I had ever been called “Hon”.

None of the clerks I knew were at the registers. I only had a few items in my cart and as I was queuing up in a line the guy in front of me, who had a cart piled high, wanted me to move ahead of him. I declined then headed for an empty line but I appreciated his offer and that he had made it to a guy in a skirt and boots. The register clerk that I got was a guy and to my surprise he threw me a smile and a pleasant good evening. He didn’t seem put off at all about waiting on me and we chatted about the rain.

By the time I got outside, the sun was out again so I didn’t have another mad dash across the parking lot.

I stopped for gas on the way home and a few folks noticed but no one said a word.

I really like the look of this skirt. Its about a size smaller than I normally wear and a straight cut which makes me look a but thinner than I normally do. I think the message is that I should loose a couple more pounds.

This skirt and boots thing is starting to become much more comfortable, and habit forming.

JeffB -

Thanks for the kind words and congratulations on you outing.

[JeffB]

This skirt and boots thing is starting to become much more comfortable, and habit forming.

While I enjoyed reading your latest outing (memo: keep an umbrella in your car for instances like what happened to you), I was taken in by that sentence above. It appears that you're reaching your comfort level when it comes to your skirt and boots combo, that you have no trouble coming and going whenever you chose in the clothes YOU want to wear, not what society wants you to wear. As for the habit forming part of the equation, only you can allow that to happen. As always exercise caution and restraint. But enjoy what you're doing.

[Bubba136]

TBG! It appears, as you've commented, you fear of appearing in public in alternative clothing is fast disappearing. While you apparently circulate through many of the same places, employees that work in the stores are becoming used to seeing you and are overlooking the dressing and focusing on the individual (as it should be). JeffB: Your wearing a skirt in public reminds me of your former self, when you wore your pumps every day at work. Back then, I always thought you dressed very nicely in clothing that complemented your shoes. Now, it appears you're carrying your fashion sense over to wearing skirts. You looked great in the picture. You and TBG are great inspirations to us.

[JeffB]

JeffB: Your wearing a skirt in public reminds me of your former self, when you wore your pumps every day at work. Back then, I always thought you dressed very nicely in clothing that complemented your shoes. Now, it appears you're carrying your fashion sense over to wearing skirts. You looked great in the picture. You and TBG are great inspirations to us.

Thanks for the kind words, Bubba. I appreciate it. I simply do as best as I possibly can when it comes to dressing up for public outings as I don't want to look foolish or outlandish. The challenge of being a man and looking nice and not freakish in a skirt is a considerable one, but it's a challenge I've seriously taken up. What you've seen is just the start as I mean to work really hard at my image so I'll look my very best. It's the least I can do so I don't bring disgrace or humiliation to our community of fashion freestyling men.

[Thighbootguy]

I had a great outing this afternoon. Jeff looked so good in that denim skirt I thought I would try one and I must admit the idea of wearing a skirt that would blend in, although sounding like an oxymoron, was a new concept to me. I had never tried to blend in. Anyway, I pulled out a stretch denim skort that was just a few inches shorter than the red leather one I wore yesterday. The hem of the skirt was just above the tops of my boots. I went out wearing the skort, a black sleeveless turtleneck, my black leather thigh boots with 5” stilettos , and a black leather purse. It’s hard to mess up black and denim. I have been carrying the black leather purse full time for over a month now and have gotten quite used to dealing with it. My first stop was the my favorite thrift emporium. As I walked in two black ladies walked out and one said, “Oh there’s them boots” and gave a rolling laugh that only a large older black lady can give. “Don’t you have a pair of those in red?” “No I don’t but I do have them in white and blue.” I was treated to another laugh then she said, “You take care now.” In the store I wandered around a good bit and I found a brown suede light coat and a blue silk blouse that I thought would go with the denim skort. My total bill was $5. After the thrift store I went into Hanover Fabrics and browsed around until I found a needle threader. Next I stopped in Payless but didn’ t see anything I was interested in. Finally I went to the St. Vincent DePaul where the clerk picked out a dress for me. I had to park a block away and walk to the store. A few heads turned. In the store, I wandered around and then spotted the same clerk. She was looking down so the first thing she saw was my boots. She looked up and gave me a big smile and a warm greeting. She was busy so I wandered around some more but didn’t find anything I wanted. When she wasn’t busy I said, ”I didn’t find anything this time but I wanted to thank you again for the help last time.” She said, “I’ve been keeping my eye for something you would like, but I haven’t seen anything.” I thanked her and headed back to my car. This time I got an undecipherable comment from a passing car. To finish the day off I headed for the Museum. This is the first time I have worn a skirt or skort to the museum. Previously I always wore jeans or shorts. In the parking lot, I remembered the advice about pairing something classy with something outrageous so I pulled out the blue long sleeved silk blouse and put it on over the black turtleneck. Classy top, casual skort and outrageous boots. I walked in and the guard greeted me warmly so I picked up a stool and headed up the stairs to a gallery. I found a painting I wanted to work from and placed the stool but when I sat down (these are low stools) I realized I was wearing a skort and had to keep my knees together. Ah the sacrifices one makes for fashion. All the guards greeted me like nothing was different. After I finished, I headed back to my car and the guard in the parking lot, who I always thought was a little stand offish, hailed me and said he had missed seeing me for a while. (He isn’t always on duty when I’m there). I must admit I really felt comfortable in the denim skort. I’m not sure I would feel that way without my boots though. For me the first thing is wearing my boots, and the skirt is the secondary issue. I sure had a fun and enjoyable outing.

[JeffB]

TBG: So, I inspired you to wear a denim skirt after you saw my picture, eh? Well, isn't that special! Glad to read that I was a positive influence on you. Sounds like you had yet another enjoyable outing, I continue to be amazed at how easy you go about in your boots without raising any sort of fuss. I guess that everyone in your orbit are used to your unique look and it's no big deal to them. That's what I find so cool about reading your adventures. I also found it interesting how you said that you felt comfortable in the skirt, aided by the boots of course which are first and foremost in your heart. I can understand that fully. With that in mind, can you envision a day when wearing skirts shares top billing in your mind with the boots? Inquiring minds wanna know!

[Thighbootguy]

I wanted to see if yesterdays outing in a denim skirt was a fluke or if people really didn’t care that a guy was wearing a skirt and thigh boots so I dressed exactly as I did yesterday; blue silk blouse over a black sleeveless turtleneck, denim skort, a blue sweat band, a black shoulder bag, and black leather thigh boots with 5” stilettos.

I also wanted to test buba136’s observation that I tend to go to the same places over and over again where people know what I look like, so this time I ventured out into a different part of town that I rarely frequent. I’m still cautious and cognizant of becoming complacent about where I go so I have been in most of these stores before but it has been many months ago and today I didn’t see anyone I recognized.

First I went to Lowe’s (hardware warehouse store) where I found a parking space at least in sight of the store and I had a nice walk to the store. By the way, the temperature was around 89F on a bright sunny day. In the store I had to hunt for the item I wanted. A few heads turned and one clerk ignored me but I found what I wanted and headed for the register. I couldn’t help but stop in the power tools section and admire all the neat stuff (much to the consternation of the real guys that were drooling over the power tools. I paid for my stuff and headed back to the car all without fuss or comment.

Next I went to Sam’s and it was a typical Sam’s trip. I took my time and nobody seemed to care what I was wearing.

There was a Payless around the corner from Sam’s so I stopped in. They had a nice pair of black patent ankle strap long toed pumps in a 13W but I didn’t go for them.

The next stop was a Walmart Superstore. I had never been in there before. Again, I got a parking spot in sight of the store and had a nice walk to the store. Inside I found my items in the pharmacy then walked to the back of the store for the shoe department. The selection wasn’t worth the walk. I paid for my stuff and took the long walk back to my car.

The next two stores were next to each other and I found a close in parking spot. I walked into Barnes and Noble and headed for the computer section. They had a descent selection if Microsoft’s toys are your game but I did find a complete collection of Sir Author Conan Doyle’s, Sherlock Homes.

I walked next door to a Shoe Carnival and looked through their collection. I asked one of the clerks if all the boots were on display and she said they were (both pair) and that the boots had not come in yet.

All this time no one had said a word or even given me a second look so feeling confident and curious, I headed for Florence Mall which is a large two level indoor mall. I walked in and security guard nodded to me with a smile. I walked all through the mall, both levels, and the only shoe store I found was another Payless. As I walked in I heard a loud “love your boots” from somewhere outside the store, but I have no idea where It came from. While I was in the mall I did hear some giggles from kids and at least one OMG from behind me, but for the most part no one seemed to care. It's fun to look for reactions in the reflections in the store windows, but I saw very few.

The last stop was at a Goodwill and it was as uneventful as the rest of the day.

It seems that all my concerns about wearing a skirt with thigh boots was all in my head. No one gives a rip. However, this experience has allowed me to look at this from another perspective. If I am wearing thigh boots with 5” stilettos, it doesn’t make any difference what I wear with them (within reason). People are going to form their judgment based on my boots and anything else is superfluous. Another way of looking at this is recognizing all the opportunities it opens.

JeffB and Buba136 –

Please don’t lay “being an inspiration” on me. If you want inspiration, try a church revival meeting or listening to the presidential candidates. Don’t be inspired by a self admitted wacko that wears thigh boots out in public. Set your standards a little higher than that.

JeffB –

The boots still get top billing.

[maninkirt]

Thighbootguy I must congratulate you to your outfit and your outings. Its great! Its good to you´re feeling feeling comfotrable wearing a skirt. Its fantastic, its great! See you too is wearing a handbag, just like JeffB and me. Well Thighbootguy wearing a skirt, a handbag is a must, insn´t it? Oh thats good Thighbootguy, you too having to do a little bit of sacrifies for fashion. Must have been feeling good the guards greeted you as nothing was different.

[Thighbootguy]

I went out to some of my favorite haunts this afternoon wearing a gray T-shirt, a denim skort, and my black leather thigh boots with 5” stilettos. Casual top and outrageous bottom.

The first stop was the museum. One lady at the front desk did a double take but she had never seen me before. The stool were missing this week so I resolved to work from the benches in the galleries. This is just a s well because the benches are a little higher than the stools and I took JeffB’s advice and sat cross legged, which is impossible on a short stool. The guards chatted with me and made no mention of my different attire.

As I was sketching, one of the employees, a very attractive young lady, (not a guard or a volunteer) came through and said, “Hi, I know you’re here all the time and would like to invite you to a ribbon cutting ceremony we are having for a new exhibit.” I declined but thought it amazing that a guy in a skirt and thigh boots would be invited to anything. I worked for a little over an hour then headed to the Krohn Conservatory.

I had never been to Krohn wearing my boots and this week there was a small crowd so I parked in back, grabbed my drawing stuff and headed in. I found a bench and started sketching a plant. No one seemed to be bothered by a guy in heeled boots. I walked through the Conservatory and had a grand time.

Next, I headed to mu favorite http://www.villagediscount.com/'>thrift emporium (the one in Newport). I found a pair of light tan leather suede slacks for $8. After that I stopped in the St.Vincent DePaul thrift store.

The outing was uneventful but very enjoyable.

I have the confidence to wear just about anything that I want but when I’m wearing my boots, it changes the expectations of everyone who sees me. Rather than being seen as a guy wearing women’s stuff, the thigh boots change the image to guy in outrageous boots who is also wearing other women’s stuff. The boots are such a strong statement that everything else pales in significant. I know this isn’t a formula for everyone, but it works for me.

[JeffB]

The first stop was the museum. One lady at the front desk did a double take but she had never seen me before. The stool were missing this week so I resolved to work from the benches in the galleries. This is just a s well because the benches are a little higher than the stools and I took JeffB’s advice and sat cross legged, which is impossible on a short stool. The guards chatted with me and made no mention of my different attire.

I'm glad you've followed my advice.

As I was sketching, one of the employees, a very attractive young lady, (not a guard or a volunteer) came through and said, “Hi, I know you’re here all the time and would like to invite you to a ribbon cutting ceremony we are having for a new exhibit.” I declined but thought it amazing that a guy in a skirt and thigh boots would be invited to anything. I worked for a little over an hour then headed to the Krohn Conservatory.

Aww! You should've accepted the offer. Sounds like it would've been cool.

I have the confidence to wear just about anything that I want but when I’m wearing my boots, it changes the expectations of everyone who sees me. Rather than being seen as a guy wearing women’s stuff, the thigh boots change the image to guy in outrageous boots who is also wearing other women’s stuff. The boots are such a strong statement that everything else pales in significant. I know this isn’t a formula for everyone, but it works for me.

Hmm. An interesting dynamic. Hard to believe you rarely raise any eyebrows despite the outrageous quotent of those boots you wear. But perhaps the outrageousness is what helps you succeed in your outings. In any event, more power to you!