Boots and Skirts in Public

[JL]

I wish I could do that - wear 6+" heel boots all day. I think I'd get a few more looks than you though.

[Guest]

Jl if you can walk ok in 6 inch heels ok i say go for it.Just wear longer pants cover the heel more.The weather has been cooler here so im back wearing boots more often!!

[balletboot2000]

Donna, as ever your new pictures are brilliant. You seem very able to handle the extremity of the heels on those boots. All I can say is that I am in awe, and well done

[Guest]

Thanks ballet boot.I have a few video's on you tube also.Of the metal high heels. http://www.youtube.com/watch?v=6_-SlB_MmXM

[balletboot2000]

Hi Donna, the new vids are great. It made me put my 7" inch metal heeled boots on at the weekend. Just need some more heel time to be able to get my knees straightened out again. I'm out of practice. Please keep posting more vids, although I'm sorry that you took the one off with you smoking in your boots, that was my favourite

[Fog]

I met up with Tara after a course I was attending near Oxford Circus. We shopped for a while and after we'd parted I carried on with my Christmas shopping for Mrs F. I was wearing silver glittery tights, silver shorts and black flat knee boots. It is frustrating looking at heels in shops and knowing you can't wear them any more - never mind. I was enjoying myself. I had a look in Selfridges, tried a bit of concealer for my eyes - at £27 a pop it didn't have the slightest effect. I then went into M&S (not to be confused with S&M) - walking through the store a young female assistant looked me up and down and said "nice". I thanked her - she was charming and told me she liked my scarfe as well. I then went into one of the myriad of discount clothing shops that are at the Marble Arch end of Oxford Street. There I bought a skirt for Mrs. F, but tried it on - to make sure it fitted. It was very thin cotton, and very short, with a bit of a flair at the bottom. The mirror was outside, so buoyed up with confidence I stepped out of the cubicle to give myself the once over. I liked what I saw, bought two of the skirts. I went back to the changing room and put one of them on, and continued myshopping wearing a skirt. What amazing fun! I enjoy the freedom of wearing shorts and tights and showing my boots to all and sundry, but wearing a mini skirt with the outfit was something else. I took my coat off whenever I was inside, and some of the time I was outside. A couple of security guards in Primark said "dear dear" and I got barged by some of them who were chasing someone. I must say they're most rude, I heard a coarse voice behind me saying get out of the way, and I side stepped, only to be barged full on by someone of prop forward dimensions. All in all a fun evening's shopping - and one which I hope to repeat in the very near future.

[r1g0r]

boots and skirts are almost all i wear to work. the truly best thing about my job!

[Thighbootguy]

The weather has cooled off a bit and it has made a leather skirt and turtleneck comfortable to wear. I went shopping tonight after work wearing a medium length black leather skirt, black turtleneck, a tan suede jacket and black leather pull on thigh boots with 4” stiletto heels. My first stop was the Sam’s where I normally shop. A few heads turned and there were a few looks of surprise but that was all. The next stop was Pet’s Mart to get some cat food. Again there was a little surprise but nothing negative. The last stop was Walgreen’s Drug store and the reaction was the same. Part of what was going on was the attitude I tried to project. I gave no opening for someone to think I wasn’t doing exactly what I wanted to do or that there wasn’t anything wrong with it. I think I like the look of a shorter skirt with hose and thigh boots but like I said, it has cooled off a bit and the longer skirt was comfortable. I had a great time.

[Thighbootguy]

The weather has gone nuts. Early January and the temperature is almost 70F (21C). I was planning on wearing a brown suede coat and matching leather skirt with black leather pull on thigh boots when I stopped at Sam’s tonight but it was too hot for the coat. I stopped in the Goodwill on the way to Sam’s and I really was just looking around but I notices they were having a sale on skirts. I bought two for 99¢ each.. Both were fabric with a bit of spandex as part of the weave. One is shore and bright pink the other is black and just above ankle length. Both stretch just a little when I wear them. I decided to wear the black one with my boots into Sam’s. I knew the greeter and asked her how the skirt looked. She said it looked fine. I was not using a shopping cart so there was no hiding behind it as I was walking around the store. I shopped for a little while but didn’t buy anything. I went out the same door I had come in (entrance door rather than the exit door) which meant there were people coming in and I got to walk through a crowd that was facing me. There were a few confused looks to say the least. No comments or giggles but most folks didn’t believe there was a guy in heeled boots with a skirt walking toward them. I bid the greeter a good evening and headed out to my car. I think I still prefer jeans with boots but this is a fun look to try out. I’m not sure what I’ll do with the pink skirt unless I wear it with my white thigh boots.

[JNR]

T

I’m not sure what I’ll do with the pink skirt unless I wear it with my white thigh boots.

Deisions, decisions, decisions! Life's just full of them.

[Thighbootguy]

I have come to enjoy wearing the black fabric skirt I bought a couple of weeks ago. The length is about mid calf and it has a side slit that goes up just above my knee. I stopped in Sam’s again tonight wearing that skirt, black leather thigh boots with 4” stiletto heels, a black turtleneck and a brown suede winter coat. The skirt has a bit of spandex and fits tightly. I did make sure there were no unseemly bulges in the front. I walked through the store and got very little notice. The staff is used to seeing me and the other shoppers either didn’t notice or didn’t care. At Sam’s I do have to use a shopping cart so people seeing me from the front very often don’t notice what I’m wearing. I went to a register where a clerk who knows me was working and I asked her how the skirt looked. She said it looked fine but also that she was used to seeing me. She has told me in the past to, “dress however you want”. All in all an uneventful shopping trip. The weather, however, was cool and wet enough that I knew I was wearing a stretchy fabric skirt rather than a leather one. Later in the evening I ventured out with a different pair of black leather thigh boots and a leather skirt. This was nothing more than an uneventful walk around the neighborhood.

[Thighbootguy]

Today I took an opportunity to get away from my desk and stopped in at the local Goodwill (thrift store). There was a sign advertising skirts and blouses for 99¢. This was too good to pass up so I went in (dressed in work clothes ie. slacks and turtleneck) and looked through the racks. I found a gray wool 36” skirt and a gray and a tan blouse. I tried the skirt on and it fit very nicely. The skirt came with a narrow black belt which really manes the image. I asked the lady at the register which of the two tops went best with the skirt, and she said the gray one looked nice with it. On the way home, I stopped at Sam’s and wore the skirt, the black turtleneck, and a pair of black thigh boots with 4” stiletto heels. The skirt is long enough that not much of the thigh boot was visible, I could have work knee boots and gotten the same effect. In Sam’s, I was using a shopping cart so people really didn’t notice what I was wearing as I approached them. However, even the folks that really did see a guy wearing a long skirt and heeled boots didn’t seem to care. One thing about wearing a lined a wool skirt and thigh boots, the outfit is warm. At the register I had a clerk that has never seen me before. After she had rung up all my items, I asked her, “how does this look?” She put her hands up to her face and giggled and then gave me a smile and a thumbs up. When she composed herself, she said, “looks nice.” I think she was really trying hard not to react to a guy wearing a skirt, but when I spoke to her, she lost it. All in all this was a fun day.

[Thighbootguy]

I stopped at Sam’s last night to complete my weekly shopping. I went in wearing a brown suede winter coat, dark green turtleneck, a stretchy denim skirt, black hose, and black pull on thigh boots with 4” stiletto heels. The skirt hem hit the top of my boots. The staff greeted me like an old friend and the rest of the customers didn’t seem bothered. I did notice a couple heads turn and at least one guy came back into the isle where I was and pretended to still be looking for something but that is to be expected. I had some time so I wandered around the store a bit and just enjoyed being out. I had stopped in this same store yesterday after work and I was in a hurry. I had not pulled on my boots but went in wearing slacks and guy shoes. Not wearing my boots got more attention from the staff than wearing them does. As I left the checker at the door asked where my boots were. Tonight the same guy was at the door and gave me a smile with the comment, “Good, you got them on tonight.” I have started to notice that I am really finding a skirt and boots a comfortable way to dress, both physically and mentally. I like the look about as well as I like boots and jeans and I’m becoming more and more comfortable presenting it.

[PetePete]

Thighbootguy, I'm really enjoying this thread, thanks. Some great stories you have to tell. Although it'll take me a while to read it all.

[JeffB]

TBG: I continue to be amazed with how you've integrated skirts into your regular attire and how comfortable you are wearing such garments in public. I greatly admire you for your courage, though I'm sure it didn't come naturally and took a goodly amount of time for you to develop. More power to you, my friend!

[Thighbootguy]

I have a bit of shopping to do and decided to do it in a skirt and thigh boots. I was wearing a brown suede winter coat, a black turtleneck, a long black fabric skirt and black leather pull on thigh boots with 4” stiletto heels. The top of boots disappeared way under the skirt.

First I went to a fabric store in a down scale mall. I parked and walked across the parking lot and into the store and started to look around. The folks in the store seemed willing to tolerate a guy in a skirt and heels. I had to ask for help to find the item I wanted. (I was looking for a zipper for my 5” heeled boots). The clerk took me to them and I thanked her. It took a few minutes for me to make my selection and then I wandered around a bit before I went to the register. The register clerk had to come over from another part of the store and she had seen me come in. She made sure I got the correct discount on the zipper and gave me my change. No one said a word about the skirt or boots. For all I know, shoppers like me could be coming in every day (doubt it though).

I then drove to Joseph Beth Booksellers which is in an upscale mall in Cincinnati. The parking lot was packed so I got to walk about a bit outside. In the store I found a book I was interested in and sat down on a couch to look through it. Several folks wandered by but I didn’t get a second glance. The book didn’t have what I wanted so I reshelved it and headed back to my car.

There was a Shoe Carnival on the far side of the parking lot so I stopped by on the way out. The store was full of upscale bargain hunters of all ages. There were several groups of young girls and a group of guys plus all the other female customers. I was thinking that this was going to be a challenge. I started looking at some 5” pumps and what was left of the boots. On the bargain rack I found a pair of 5” stiletto strap pumps with an ankle strap. I decided to try them on. I took them over to a chair and took off one of my boots and tried the pump on. It fit reasonably well except the ankle strap was almost 2” too short. I put the pump back in it’s box and pulled on my thigh boot again. Remember I’m wearing a skirt and sitting in the middle of the women’s section of a shoe store. No one even batted an eye. Everyone chose to ignore the guy trying on heels. I left the store and headed back to my car.

I really was expecting a few heads to turn or a few giggles but, at least today, the world was tolerant of a guy in a skirt and boots. I had a great time.

-Jeffb

Thanks for the kind words.

[JeffB]

The folks in the store seemed willing to tolerate a guy in a skirt and heels.

Another enjoyable outing I enjoyed reading about, but I highlighted that particular sentence because no store or shop, small or humongous should ever turn away anybody, regardless of how he or she happens to be dressed. If someone is willing, eager even to spend their hard earned money, then the proprietors shouldn't give a damn if the shopper is a man in a skirt and heels. If anything, they should be happy to cultivate your business as good word of mouth can mean extra business, but on the flip side, bad word of mouth can sink a business. Never let anyone discriminate against you because of how you dress. At the end of the day, your money is just as good as everyone else's.

[Thighbootguy]

JeffB, your absolutely right but the “folks” in my comment were referring to the clerks and the many other customers. Maybe it was the recent eclipse of the moon, or this projecting confidence thing I keep preaching about, but everyone seemed to be more tolerant than I was expecting.

[JeffB]

JeffB, your absolutely right but the “folks” in my comment were referring to the clerks and the many other customers. Maybe it was the recent eclipse of the moon, or this projecting confidence thing I keep preaching about, but everyone seemed to be more tolerant than I was expecting.

Well, I'm certainly glad you find tolerance in the places you go. Perhaps that's because the people at that establishment are used to you and know you're no freak or deviant, just somebody with a highly eclectic sense of fashion. Heh!

[Thighbootguy]

Yesterday afternoon I stopped at Sam’s wearing a heavy dark blue turtleneck (no coat needed), a blue denim skirt, and black pull on thigh boots with 4” stilettos. As I walked in the greeter (who knew me) tried to sell me a new credit card, which meant she had to stop and talk with me for a while. As I was shopping, folks seemed to notice my outfit a bit more. I seemed to notice more heads turning but no one said a word. I stopped at one of the managers stations to ask if they were still carrying several items and she was professional and answered my questions, but not before she gave me a head to toe looking over. The second item was a makeup kit and there was no doubt about who it was for. At the register, I got the same clerk I had a week ago. (The one that gave me a thumbs up.) I complemented her on her earrings which were quite large wide gold circles. She thanked me for the comment. When we were done I asked her if the outfit I had on worked and she gave me another big smile and a thumbs up. Tonight I wandered around the neighborhood wearing chap boots with 5 ½” heels, a pink suede skirt, a pink turtleneck sweater, and a brown suede coat. I also tried a wig to change the guy in boots and a skirt image. There was no pedestrians but a fair amount of car traffic. I’m not sure I’m ready to try this in a more public venue. Even though it was around 30F the outfit was still quite warm, but it may have been the second scotch I had that made me feel that way. (The second scotch may have also been the reason I went out dressed like that.) Anyway both outings were fun.

[Thighbootguy]

I just had a great shopping trip! I had reread a post by Richie where he (justly) took me to task for not doing much in the way of coordination of the clothing I was wearing. I wanted to go shopping in a black leather skirt so I went out wearing a white turtleneck, black “19” leather skirt with t thin red belt, white hose and black leather pull on thigh boots with 4” stilettos. Even though it was 45F, I didn’t wear a coat. This outfit was basic black and white with a red highlight and, in my humble opinion, it looked good. I went to two stores that have seen me many times before. First I went into Walgreen’s and wandered around a bit. The items I wanted were on the bottom shelf so I had to exercise a bit of caution when I was bending down that low. No one (clerks or patrons) seemed to be bothered at all about the way I was dressed. The register clerk seemed to go out of her way to be chatty but didn’t mention my outfit at all. Next I went to Sam’s. I walked across the parking lot and into the store with no undo attention. I was using a shopping cart in both stores so it reduces the impact of seeing me coming. In the store I again wandered around and no one seemed to either notice or be bothered by my looks. At the register, the clerk, who had given me a thumbs up a week or so ago, gave me a nice smile. I asked her if this looked a little more coordinated? She smiled, looked me over and said, “That looks nice.” She paused then added, “I like your boots.” It doesn’t get better than that. I thanked her for her comment and headed out. At the exit the door checker, who knows me well, suggested the expected snow storm might get up over my boots. This was from a really nice guy who wants to say nice things to everyone. The lesson learned is that if I’m going to wear clothing not associated with my gender, I should to pay more attention to the coordination and try to make it look good. A good looking outfit says as much as the fact that a guy is wearing it.

[stockingstoo]

Congratulations!!! hehe sounds like you had fun and I know what you mean by the last bit...

[JeffB]

The lesson learned is that if I’m going to wear clothing not associated with my gender, I should to pay more attention to the coordination and try to make it look good. A good looking outfit says as much as the fact that a guy is wearing it.

What have I been telling you for the longest time? COORDINATE!! If you look good, you'll feel good! Plain and simple! Observe what women wear or peruse fashion magazines so you can get ideas for outfits that would suit you best. I would agree that your ultimate goal is to be complimented on what you wear, regardless of if what you wear is for the other gender.

[Thighbootguy]

Ok Jeff. I feel like the mule that the mule driver just hit in the head by with a 2 by 4. You have my attention.

When I have been going out I never thought I looked bad, I just hadn’t put extra effort into looking good. This “looking good” is something new for me. When I dress for work, I have several pair of slacks and a bunch of shirts that all work (more or less) with one another, I really don’t pay that much attention. Work just isn’t a place I dress for. A suit and tie and not part of my wardrobe any more (except for one suit, that has a matching skirt).

I have always passed my own test of liking what I see in a full length mirror before I go out, but it looks like I have to train my eye to be more discriminative.

An aside: People often tell me they can’t draw. That really is an incorrect statement. Few people do not have the hand coordination to be able to make a pencil mark on a page. The skill of drawing is seeing what you want to draw. You have to be able to see the difference between a light and dark shadow and where something is highlighted. Once you can see those values it is easy to put them on paper. Drawing is 90% seeing and 10% manual dexterity.

Looks like I have to start paying attention to what clothing “looks good”.

Another aside: There are as many forms of drawing/painting as there are artist but you can generalize the style. For example: modern, renaissance, landscape, portrait, realistic, impressionism,… I happen to really like the Dutch Masters but others think their too stiff. Some really like modern art but I won’t even bother to go into the gallery.

I’ll have to get a working definition of “looks good”. I suspect I shouldn’t trust my eye at this point, rather, I should take your suggestion about fashion magazines and paying attention to what females around me are wearing. That is going to be tough because what “looks good” to me may not be all that great (or appropriate). For example, I thought the leather skirt and the thigh boots really looked good but a lot of what I have been reading says it may not be “appropriate”.

Is there a subtle difference in what clothes “look good on me” and what “I look good” wearing”? Should I wear something that “looks good”, even if I don’t like the look on me? Or, should the “look I like” have more influence? All of a sudden what I like or what I think looks good gets back into the equation and I’m back where I stated. I’m back to the question of why I like to wear thigh boots in public in the first place.

This was a lot easier when I was just an eccentric IT geek that just likes to wear thigh boots.

[lorriette]

Ok Jeff. I feel like the mule that the mule driver just hit in the head by with a 2 by 4. You have my attention.

When I have been going out I never thought I looked bad, I just hadn’t put extra effort into looking good. This “looking good” is something new for me. When I dress for work, I have several pair of slacks and a bunch of shirts that all work (more or less) with one another, I really don’t pay that much attention. Work just isn’t a place I dress for. A suit and tie and not part of my wardrobe any more (except for one suit, that has a matching skirt).

I have always passed my own test of liking what I see in a full length mirror before I go out, but it looks like I have to train my eye to be more discriminative.

An aside: People often tell me they can’t draw. That really is an incorrect statement. Few people do not have the hand coordination to be able to make a pencil mark on a page. The skill of drawing is seeing what you want to draw. You have to be able to see the difference between a light and dark shadow and where something is highlighted. Once you can see those values it is easy to put them on paper. Drawing is 90% seeing and 10% manual dexterity.

Looks like I have to start paying attention to what clothing “looks good”.

Another aside: There are as many forms of drawing/painting as there are artist but you can generalize the style. For example: modern, renaissance, landscape, portrait, realistic, impressionism,… I happen to really like the Dutch Masters but others think their too stiff. Some really like modern art but I won’t even bother to go into the gallery.

I’ll have to get a working definition of “looks good”. I suspect I shouldn’t trust my eye at this point, rather, I should take your suggestion about fashion magazines and paying attention to what females around me are wearing. That is going to be tough because what “looks good” to me may not be all that great (or appropriate). For example, I thought the leather skirt and the thigh boots really looked good but a lot of what I have been reading says it may not be “appropriate”.

Is there a subtle difference in what clothes “look good on me” and what “I look good” wearing”? Should I wear something that “looks good”, even if I don’t like the look on me? Or, should the “look I like” have more influence? All of a sudden what I like or what I think looks good gets back into the equation and I’m back where I stated. I’m back to the question of why I like to wear thigh boots in public in the first place.

This was a lot easier when I was just an eccentric IT geek that just likes to wear thigh boots.

I would like to say that I agree with jeff re: co-ordinate, but can see your point on personal look and likes.

The question would seem, do you want/ are happy to be seen as an eccentric man?

There is no wrong answer, but wearing co-ordinated clothes, suited to a person of your build and agegroup. should make you stand out less. You have said in the past that this is not an issue, and most members here support one's right to wear what pleases them. Each of us will make a personal decision, and therefore are prepared to accept that adverse reaction is a strong possibility. Is blending in, use of make-up, falsies or other to look more female, actually a cop out from our desire to be ourselves?

[JeffB]

TBG: Fashion and what "looks good" is a highly subjective topic, fully open to personal interpretation. In other words, it all depends on the mindset of each and every individual. While I suggested that you observe what women wear to get ideas, at the end of the day, only you can decide upon what your own special look can and should be. You have to be true to yourself and your own sense of style. Don't copy what others wear, make a certain outfit yours and yours alone. But at the same time, it certainly wouldn't hurt to tidy up your style, coordinate your colors, try as best you can to make things match, wear colors and/or styles you think would best suit or flatter your body style and dimensions. When out in public, your idea should be to look good, but not stand out like a sore thumb, even though you're already doing that as a man in miniskirt and thigh boots, strive to make that look stylish so that passersby don't say, "Look! It's a man in women's clothes!" rather they say, "Hey! Doesn't that guy look good?" It's certainly important to pay attention to what you wear. Don't just throw on anything that suits you, examine an outfit with a critical eye, examine each and every aspect and ask yourself the following question: "Will this outfit allow me to blend in while not looking outrageous?" Leather skirts are nice, but not suitable for each and every situation. How often do you see women out and about in leather skirts? Not often I'll wager. Knit or denim skirts would be better for more casual outings, especially the outings you regularly enjoy. Save leather skirts for occassions that call for dressing up. And I've mentioned this to you before: Thigh boots aren't appropriate for any and all sorts of outings. Well, I hope this advice will be of use to you.

[JeffB]

Is there a subtle difference in what clothes “look good on me” and what “I look good” wearing”? Should I wear something that “looks good”, even if I don’t like the look on me? Or, should the “look I like” have more influence? All of a sudden what I like or what I think looks good gets back into the equation and I’m back where I stated. I’m back to the question of why I like to wear thigh boots in public in the first place.

Sure, this isn't easy territory to navigate, and it can be chock full of landmines. Again, it's all about one's personal interpretation of style and fashion and one's own views of what "looking good" really is. You could ask a dozen people what "looking good" is all about and get a dozen different answers. Case in point: I've seen plump girls and women sashaying about in low rise jeans, exposing the ever dreaded muffin top look for all to see, dreadful to say the least, but in the mind of that person, she's the greatest thing since sliced bread, everyone around such a person would look upon her with amusement, perhaps even revulsion because she just doesn't look good, but she just see or accept the obvious. Given your current preference for short skirts and thigh boots, you might be looked upon by the world at large in the same way as muffin top girls, blinded as you by what you enjoy wearing. Don't get me wrong, that's not a bad thing, just the inevitablity of being in the public fishbowl.

But to address your question directly, I think your goal should be to wear clothes that not only look good but appropriate for the setting you happen to be in, even if said style might not be your cup of tea. You don't want to stand out like the proverbial sore thumb, endeavor to look tasteful, not trashy or extravagant, that point I can't stress enough. Good style, AND good taste is important. I think that, given your age, you should strive to establish a particularly high level of taste and style in the clothes you wear, like say suits with knee length skirts and turtlenecks, and while I know you find it hard to part with your beloved thigh boots, but, like I said previously, they just don't blend in every public setting. You have to bring yourself to realize that fact and adjust your wardrobe accordingly. At least try knee boots with the outfit I just mentioned and see how you look. I think you might be pleasantly surprised. Look at an over goal as this: dress to impress, blow people away with your style.

Again, observe women and what they wear in a wide range of societal settings, make notes of what styles works best, then experiment until you find a look that you'll ultimately be comfortable with.

[derf]

Yesterday I stopped by a convenient store in a denim miniskirt and 4.5 inch Nine West Pumps. The lady at the register was quit nice and commented that I had great legs. I was not wearing a wig but rather showing my balding head. She asked how I could walk in heels that high and I told her that these were not high compared to what I normally wear when wearing heels. She said she thought I looked great and asked me to come back sometime with higher heels on. I asked her if she thought it looked strange and she said maybe to some people in this area but not me. A very gratifying experience and one that I shall not soon forget.

[Thighbootguy]

Derf-

I haven’t had the nerve to go out in pumps and a skirt. I have no problems wearing a skirt with thigh boots but something stops me from wearing pumps (at least with a skirt). I think I fail my look in the mirror test, I just don’t like what I see. I guess my legs aren’t that great.

Isn’t it great to have someone comment (positively) on your heels and overall look?

Sounds like you had a great outing. Thanks for sharing it.

[JeffB]

Derf-

I haven’t had the nerve to go out in pumps and a skirt. I have no problems wearing a skirt with thigh boots but something stops me from wearing pumps (at least with a skirt). I think I fail my look in the mirror test, I just don’t like what I see. I guess my legs aren’t that great.

TBG: It's certainly good that you can look at yourself with a critical eye and understand what will and won't work for you. To quote a line by Clint Eastwood in Magnum Force (the second Dirty Harry movie), "A man's just gotta know his limitations". You have to go with what you know will look good on you, as long as you can recognize that, you'll succeed in developing your special look. By the way, at the risk of tooting my own horn, I like to think I look damn good in a short skirt and pumps. Heh!