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The Jaunts of JeffB!


JeffB

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Jeff,

Congratulations on your latest jaunt. I always enjoy reading every one of yours. As for the jitters, in my case, when I go into a place where there is a room full of men, and I know I'm the only man wearing 5" stiletto heels, yes, I get the "jitters" and for all of the reasons mentioned. It is a little nerves, a little excitement, a little enjoyment, and a little caution rolled into one big emotion. But I know to overcome the "jitters" I just have to move forward and experience the moment and the joy of all reactions I receive. As as previously mentioned, do not put myself in harm's way. As I have stated in previous posts, I won't walk into a redneck biker's bar in 5" stiletto high heels. There have been a few places where I went thinking there would be no harm or confrontation, then there was. I just kept my cool and took the necessary steps to avoid the problems.

Keep the jaunts going and posts coming!

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I found what Thighbootguy said about "take your thigh boots with you the next time you go out for a jaunt and when the jitters strike put them on instead of the pumps" was really interesting too. The few times I've worn my heels in public I've preferred to be very subtle about it, which means if I do get strange looks I know it's because I'm a guy and that a girl wouldn't get strange looks in the same outfit, whereas in thighboots a girl or a guy is just as likely to attract attention. I guess I'm saying that in pumps it'd be me getting the reaction, whereas with the thighboots perhaps it's the boots getting the reaction and maybe it's easier not to take that so personally.

SleekHeels – My apologies in advance if I have gotten this all wrong but…

From your comment about being subtle about wearing heels leads me to think you try to hide them or at least wear them so they won’t be noticed. This is exactly the opposite of what I try to do with thigh boots. I leave no doubt in the observers mind about what I’m wearing and that I don’t care if they see what I’m wearing. No one can think, “I’ll bet he thinks I don’t notice his heels” which is what a lot of us fear that someone is thinking. I don’t have to worry that someone will discover I’m wearing heels and that goes a long way to reducing the fear of going out in public. I suspect gals wearing thigh boots have adopted the same strategy because wearing thigh boots is still something that is different (even as popular as they were for the gals this past fall).

As for getting a reaction and taking it personally, how would you feel if someone said, “Hey, nice heels” or “Nice boots”? I’d take it personally. I suspect you were thinking more negatively like someone saying, “Hey, he’s wearing heels (snicker)”. The question is how you mentally deal with that. If you were already in the mind set that you were hoping no one would notice, then you’re stuck with the guilty feeling that you were found out. However if you have adopted the mindset that you don’t care, then two things happen:

  • 1) you project that confidence and you probably won’t get the negative comment, and
  • 2) you are able to let negative comments/reactions bounce off with little or no effect.

For me, wearing thigh boots screams, “I DON”T CARE” and that empowers me to wear whatever else I want, hence my comment to JeffB about wearing thigh boots instead of pumps to reduce the jitters.

TBG

I dream of a world where chickens can cross roads without having their motives questioned.

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From your comment about being subtle about wearing heels leads me to think you try to hide them or at least wear them so they won’t be noticed. This is exactly the opposite of what I try to do with thigh boots.

You're right, before I wore heels in public my mindset was totally "how can I wear them but not get noticed"... but even after just the first time when I realised how invisible the heels were I found myself a little disappointed not to be noticed. I think I'm now at the stage where I'd be happy to be noticed by cool open-minded people (or even by narrow-minded people who might gasp/giggle) but not be noticed by people who'd get abusive. I totally admire and respect your confidence and "I DON'T CARE" attitude, but I guess there's "I don't care what people think" (which is bold) and "I don't care about my personal safety" (which is reckless). Personally I dont care for peoples prejudices but I do care what people think in the sense that I'd like to portray a positive image of guys in heels and dispel those prejudices, and IMHO we do that through diversity so people can't generalise "guys in heels this" or "guys in heels that".

To that end, when I say "subtle" I mean that I'm not trying to shock, but I try to incorporate my heels into an overall appearance that blends in with everyday appearance and wouldn't look out of place on a woman (and shouldn't look out of place on a man). It's not that I don't want to be noticed at all, I'd just personally rather be noticed "oh?:-?" or even "cool:smile:" rather than "whoah!:eyecrazy:" (not that any one is better than the others, I think they all help the cause in different ways, it's just personal preference and comfort).

As for getting a reaction and taking it personally, how would you feel if someone said, “Hey, nice heels” or “Nice boots”? I’d take it personally. I suspect you were thinking more negatively like someone saying, “Hey, he’s wearing heels (snicker)”.

Thinking of it like that, sure I would take “Hey, nice heels” personally and it'd make my day... and even “Hey, he’s wearing heels (snicker)” I take constructively because every giggle's a step closer to changing someone's mindset. But negative for me means abusive reactions from people who aren't capable of tolerance or changing their mindset at all.

SleekHeels – My apologies in advance if I have gotten this all wrong but…

A different perspective is always more interesting than the same old thoughts bouncing around in my head. Your thoughts are very much appreciated.

If you like it, wear it.

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Thanks for the most recent comments, everyone. They certainly made for good reading. I would agree with SleekHeels that "jitters" can come from nervousness or excitement, I experirenced the former while in the car, then the latter when I left it as I embarked on a new adventure in freestyling. Regardless of the situation, it is important to remain in control and not let things get away from you, and I do my best to stay grounded while on my little trips. But it's all part of the deal. Say, roniheels, you want jitters? Try going into a men's room while wearing a skirt! Did that once, quite an experience to say the least! HA! On the topic of subtlety, I don't know if I qualify for that when I traipse about in a skirt and heels, or even thigh high boots, but I don't worry much about that, I simply do my best to blend in as best I can with whatever surroundings I happen to be in and leave it to the imagination of passersby to form their own opinions about me, be they good or bad, some may think I look cool, others might think I look freakish, but it doesn't matter either way, I simply go out and about and have fun. That's the important part of the whole equation. Meanwhile, TBG is quite right when he said that when you wear thigh boots, there is NO hiding, you are out there for all to see, but if you exhibit and calm, cool, don't care at all demeanor, you'll be able to go far. And besides, wearing thigh boots is fun, but with the weather warming up considerably, I'll have to put them away until September. But hey! Warmer weather means more opportunities to wear skirts! HA!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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I totally admire and respect your confidence and "I DON'T CARE" attitude, but I guess there's "I don't care what people think" (which is bold) and "I don't care about my personal safety" (which is reckless).

Part of my "Wearing Thighboots is Fun" sermon is not becoming complacent about where you go while wearing them. I have developed a list of places I go wearing them without any concerns, but whenever I go to someplace new I always try to size up the place (and the people) first. Even when I'm in one of my comfortable places, I'm still a little bit wary, especially if there is a new group of people. There is no sense in going out looking for trouble. I think keeping a heightened sense of awareness when I'm out is one of the reasons I'm exhausted by the time I get home, and why it's such a joy to find a place where the crowd really doesn't care what I have on my feet.

JeffB – Sorry, I didn't mean to hijack your thread.

I dream of a world where chickens can cross roads without having their motives questioned.

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JeffB – Sorry, I didn't mean to hijack your thread.

Nahhhh! Don't worry about it. The conversation has been fascinating.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Men's room in a skirt.... you know, when you gotta go - ya gotta go. Borders book store wasn't too bad, usually empty. Surprisingly, crowded Airport wasn't that bad either - everyone almost to busy to notice while I track for the nearest open stall, luckily I never have had to wait. I've got the most looks and sneers at the convenience store... Never a nasty comment, but at 6'5" and 220lbs, mustache - even in a skirt who's to complain?

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Men's room in a skirt.... you know, when you gotta go - ya gotta go. Borders book store wasn't too bad, usually empty. Surprisingly, crowded Airport wasn't that bad either - everyone almost to busy to notice while I track for the nearest open stall, luckily I never have had to wait. I've got the most looks and sneers at the convenience store... Never a nasty comment, but at 6'5" and 220lbs, mustache - even in a skirt who's to complain?

Who indeed? HA! I'm 6-2, 220, but clean shaven, still, I suppose I cut a rather imposing figure, even when wearing a skirt and heels! Double HA!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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When you got to go, it's a now factor ............

Clicking though a swimming pool changing room does get some attention too.

Its a do it and get out - I didn't look at any faces.

reminds me

I think there was an ATHENA poster of a guy in a skirt having a pee in the middle of a busy urinal.

Al

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5/28/2011:

With summer having arrived a tad early, what with temps in the mid to upper 80's, but with plenty of sunshine, it was time for jaunt #97, and here's today's outfit:

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A woman's blue camp shirt (size 1X) from K-Mart, the a.n.a. jeans which I've come to love wearing, and a brand new pair of shoes, the Pleaser, "Vanity 420" pumps in black leather that I ordered from Amazon.com little over a week ago. You can get a closer look at them here:

http://www.shoeluxe.com/v/vspfiles/photos/PLEASER-VANITY-420-PUMPS-BLE-2T.jpg

I've been eager to get my hands on these shoes for some time now, and they were certainly worth the wait, the fit, the style, the easy to walk in four inch heels, THIS, boys and girls is truly what a gorgeous, plain black pump is all about, and why I love wearing them. Even without a break-in period, the Vanity shoes were a pleasure to wear, after all, we're talking about leather which molded itself to my foot and felt like they became an extension of my own feet. So, it was off to downtown Philly to visit my local comic book shop, after parking half a block away from the store, I casually strolled to the store, catching the curious eye of a couple of older gentlemen I walked past. Once in the store, I spent a good twenty minutes there, and even got into a discussion on war movies, what with this being Memorial Day weekend. I'm sure I've mentioned this before, but the staff are long used to seeing me in pumps, thigh boots, even the occasional skirt.

After that, it was off to South Jersey to goof off for awhile. My first stop was to the Cherry Hill Mall where I waltzed right in, headed to the food court for lunch, wandered about for a bit, then headed to Penney's to pick up an item I had placed on order. More on that later. I got a few turned heads and double takes here and there, no doubt people could HEAR me coming, given how pleasantly loud the heels were before they SAW me, and once they did, no doubt some wondered what was wrong with this picture while the majority of passersby didn't pay me a moment's worth of attention. I suppose that was cool with me, I've trained myself to react to both indifference and people who walk up to me with questions or comments about my footwear. What would they say if I had been approached and told that person that in addition to the shoes, everything else I had on was from the women's side of the aisle. I must say that it's rather fun to be in this sort of "stealth mode". Heh!

Leaving Cherry Hill, I head down the road to Moorestown Mall where I checked out the new Pirates of the Caribbean movie (it was pretty good), then headed across the road to Barnes & Noble for some quiet time with a drink and some magazines, finally, Best Buy where I wandered the aisles for nearly an hour before leaving with the first two Alien movies on Blu-Ray. From the multiplex, to a bookstore to a huge box electronics store, I was exposed to all sorts of people, young, old, male and female and inbetween, and, for the most part, I went ignored during the course of my travels. Another day, another successful jaunt, and that pleased me. By the by, as for that parcel I picked up from Penney's....it was a dress. As I promised (or threatened, depending on your point of view), I'm going to wear a dress on my 100th jaunt since I began this thread, and I mean to follow through on that promise. Stay tuned....

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Nice look Jeff! I love the pumps! Have you noticed that after a while people just become conditioned to seeing you in heels and at times other articles from the female side of the store. I notice in my own outings that they have become no events. Would you say this is happening to you too? THX

Shafted, the boots that is! View my gallery here http://www.hhplace.o...afteds-gallery/ or view my heeling thread here http://www.hhplace.org/topic/3850-new-pair-of-boots-starts-me-serious-street-heeling/ - Pm me if you want fashion advice or just need someone to talk to.

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Nice look Jeff! I love the pumps! Have you noticed that after a while people just become conditioned to seeing you in heels and at times other articles from the female side of the store. I notice in my own outings that they have become no events. Would you say this is happening to you too? THX

Oh, yes, it has! Of course, I've always subscribed to the belief that people are too wrapped up in their own lives and affairs to worry or care about a guy wearing women's clothes and shoes, and that is certainly is the case from what I've seen of passersby while on my little adventures. And now that I'm wearing women's clothes full time on my outings, it's made things all the more fun for me as well.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Oh, yes, it has! Of course, I've always subscribed to the belief that people are too wrapped up in their own lives and affairs to worry or care about a guy wearing women's clothes and shoes, and that is certainly is the case from what I've seen of passersby while on my little adventures. And now that I'm wearing women's clothes full time on my outings, it's made things all the more fun for me as well.

Jeff,

First of all, nice outfit and as always very pretty high heels. And congratulations on your latest jaunt. But I totally agree with your statement about people seeing you in high heels. These days life moves so fast and people are wrapped up in their own agendas. When I am out in public wearing high heels, anymore I get a look, maybe a comment, then it's back to everyone's own business. I still enjoy the looks and comments, but sometimes the "non-reactions" catch me off guard, if that makes sense.

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5/29/2011:

After nine straight outings in jeans, I decided that it was WAY past time to do a jaunt in a skirt for the first time since late February. Wow! HAs it been THAT long? Incredible! Anyway, here's what I wore on jaunt #98:

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A red polo shirt, my Old Navy peasant skirt, the Pleaser "Vanity 420" pumps (bare legs, too hot for hosiery), a nice black fabric belt and my black faux croc handbag. With temps projected to be in the upper 80's, I wanted to dress loose, casual but smart at the same time. I know I've dwelled on the subject of overdoing my attire on Sundays, but, in my mind, if I'm going to expose myself in public wearing a skirt and heels, then it was important to look as nice as I possibly could. My main stop for the day was Parx casino in the northeast for a wee bit of fun gambling. Funny thing, unlike last Saturday at King of Prussia when I struggled for something like ten minutes to climb out of the car while wearing long jeans, when I arrived at the casino parking lot, I hopped right out without a moment's hesitation while garbed in a skirt and strolled right on in the place, pretty as you please. When I think back on that, I find it all rather funny.

Now, for any newbies wanting to enjoy some public heeling, a casino is a great place to be because nobody pays you any attention since they're all busy with the slot machine or table game of their choice and have zero time to acknowledge a guy wearing heels, and since the floors are carpeted, no one's going to hear your heels and thus be distracted by them. That was the case with me as I strolled right through, playing a slot machine here, a slot machine there or watching others play, and win some money which, sadly I didn't. My $100 bucks (my limit for casino trips) went plenty fast, I was in an out in little over an hour, but hey, I don't go in those places to strike it rich, just to have some fun, and I always accomplish that task, whether I come away with cash or not. And the whole time I was in the place, no one gave me so much as the time of day, since I knew that going in from past trips to Parx, I was fine with that since it was what I expected.

After leaving Parx, the money I lost already a distant memory, I head back into town, then out to the western 'burbs and Borders in Springfield. Just like at Parx, I hopped right out and headed to the store, a good breeze was blowing at the time and it blew my skirt while I walked, a most pleasant feeling when combined with the sharp clicking of the Vanity's heels, I walked tall and proud (but then, I always do) and felt great to be wearing what I like instead of what society tells me I should wear. Once inside the store where there was a decent crowd for mid-afternoon on a Sunday, I grabbed four Mac magazines, bought myself a large iced tea and retreated to the lounge area to read and enjoy my beverage. Over the course of an hour and a half, people came and went while I read and drank, my legs purposely crossed like a woman, and no one gave me the time of day. Oh, I'm sure people saw me and wondered what was going on, but no one asked.

Once again, another successful outing. After three months, it felt damn good to be wearing a skirt again, and on a day as hot as this one was, I didn't want to be constricted by pants or jeans, so my loose, breezy peasant skirt made for the perfect accessory on my latest adventure. Despite the money I lost, in the end, I was very much a winner.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Jeff,

First of all, nice outfit and as always very pretty high heels. And congratulations on your latest jaunt. But I totally agree with your statement about people seeing you in high heels. These days life moves so fast and people are wrapped up in their own agendas. When I am out in public wearing high heels, anymore I get a look, maybe a comment, then it's back to everyone's own business. I still enjoy the looks and comments, but sometimes the "non-reactions" catch me off guard, if that makes sense.

Oh, it does make sense, mainly because the sight of a man wearing high heels is still looked upon as odd or unusual, so you expect all sorts of reactions from all corners of the public. But when you don't get any reactions, despite how you might be dressed, you find yourself non-plussed from the lack of notice. God knows I wonder at times about that more than you do regarding why I get no reactions, especially when I'm out and about in a skirt! Again, it's all about the public having more important things to concern themselves than us. But hey, that's all part of the deal, sometimes you're the star, and other times, you're just an extra to be ignored. I don't mind the latter.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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So lost your shirt, but not the skirt.

HA! Exactly! Couldn't have said that better myself! Bravo! :)

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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JeffB, your previous tighter fitting shirts look great tucked into your jeans, but with the more recent looser-fitting shirts I guess you also have the possibility of leaving the shirt outside the jeans for a more floaty look. I was just wondering if you've tried that and whether you feel that look works for you or not? I only ask because I'm often in two minds about whether to wear a shirt in/out and figuring out which option works better with male shoulder/waist/hip proportions, and it's always interesting to hear how others make that work for them.

If you like it, wear it.

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JeffB, your previous tighter fitting shirts look great tucked into your jeans, but with the more recent looser-fitting shirts I guess you also have the possibility of leaving the shirt outside the jeans for a more floaty look. I was just wondering if you've tried that and whether you feel that look works for you or not? I only ask because I'm often in two minds about whether to wear a shirt in/out and figuring out which option works better with male shoulder/waist/hip proportions, and it's always interesting to hear how others make that work for them.

Hmm! Good question! To be honest, I'm not too much a fan of wearing shirts outside jeans or skirts. I tried that once and it didn't do anything for me, I guess that's because as a man, I don't have the required shape women have to make that look work to its fullest. Much as I liked the tighter shirts, the looser ones afford me more comfort, especially now that spring is here and it's been hot for awhile now. I can only suggest you experiment with both looks and see what works best for you.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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JeffB –

Sounds like you had a grand time but it seems the casino is an expensive place to heel.

I’m discovering that the important thing in not how others see us, rather how we see ourselves. I already know how most people see a guy wearing a skirt, what I am discovering is how I see myself wearing one is what is most interesting. It is a real shift of mental gears to see yourself in a skirt as “normal” rather than as “doing something different”. Its kind of like how I now see thigh boots as just another pair of shoes.

I dream of a world where chickens can cross roads without having their motives questioned.

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JeffB –

Sounds like you had a grand time but it seems the casino is an expensive place to heel.

Which is why I only go there two or three times a year. I don't have THAT much disposable income! :)

I’m discovering that the important thing in not how others see us, rather how we see ourselves. I already know how most people see a guy wearing a skirt, what I am discovering is how I see myself wearing one is what is most interesting. It is a real shift of mental gears to see yourself in a skirt as “normal” rather than as “doing something different”. Its kind of like how I now see thigh boots as just another pair of shoes.

Good point there. I've found myself having become increasingly more comfortable wearing skirts on my little adventures, since I already know how the public at large might react to what I wear, I no longer give that much thought. My goal is to enjoy myself on my outings, and I can't do that if I wonder how others view me.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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The only thing I could think of when I read the very first page of the thread for myself, and No offense to any of you, is that the first three posts/-ers were all nearly 10 years apart from one another!

I personally saw that as the "best of three generations", if no one minds me saying that :) It would probably take me some time to read through them ALL, but I think it would be worth it.

First thing it made me think of, though (I MAY have mentioned it either here or another thread long ago), is the movie Bruno (not the mediocre, comedic version; the older, more "controversial" movie), about a little boy with a taste for girl's wear, as influenced from the mom. I just saw JeffB as an older version of the little boy, racial differences aside, though. And I must say.... we need more Jeff! lol

Formally "HHDude"

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HHDude: Ask, and you shall receive!

6/4/2011:

My 99th jaunt since I began this thread was an experiment as from the time I first began heeling, I've sought to expand my horizons, to push the envelope as best I could which I knew would eventually make me a better freestyler. And so, here's today's outfit:

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A navy polo shirt (women's), the a.n.a. jeans and the "experiment" which were on my feet: Pleaser "Seduce 420" pumps with five inch heels, my first time in heels that high. Here's a better pic of the Seduce shoes:

http://www.shop2cart.net/global/hft_image_feed.php?w=300&i=/usr/local/apache/htdocs/shop2cart.net/files/product/9791.file_a.jpg

Like I said, I've sought to push the envelope, so I wanted to see what it was like to go outside my usual comfort zone by wearing five inch heels on a jaunt. The closest I've come were the Payless 4 1/2 inch "Hilt" and the "Jamie" platform pumps, but this would be new. I don't mind telling you I had no idea how much of a vast difference a mere one inch could make when it came to shoes, hopping out of the car after I arrived in town (no hesistation at all), I had to retrain myself on the fly to stand, using my calf muscles in a new way compared to the three and four inchers I'm long used to wearing, then came walking as I crossed a wide street to tap an ATM machine, that too was a bit of a challenge as I had to shorten my stride and walk slower while making sure to maintain proper posture. Oh, yeah, and I had to do all that while maintaining my usual cool and calm demeanor, plus ignoring a couple of odd looks from motorists while I crossed.

The more I walked, traversing half a block to the machine and back, the easier it became to handle the higher heels, and that helped to make my little experiment all the more worthwhile, and the increased confidence was great too. Back in the car, it was off to my favorite comic book shop to buy this week's new books, had to park little over half a block away from the store, which meant more walking to further acclimate myself to the heels, getting used to walking was the chief goal, I had to make my gait look fluid and natural, like I had been walking in such shoes for years and years, it wasn't easy right out of the chute, but I was getting used to them. In the store, came the next test: prolonged standing as I spent nearly half an hour between picking up new comics and chatting with the staff and a customer about Nicolas Cage and Jean-Claude Van Damme flicks. Seriously. But no one paid my footwear any mind, and I actually like what I wore was no big deal either.

After leaving the shop, it was off to South Jersey, first stop, Cherry Hill Mall where I calmly walked into the Penney's which was close to my destination, the food court and lunch, a few shoppers, passersby and staff turned to glance at me, but, for the most part, I was ignored, despite how I no doubt towered over the masses. The food court was little over half full at little past noon, got more glances, some giggles from a couple of black teenage girls who stared at the shoes while waiting in line at Subway, but I ignored them like others ignored me, bought my order, went to a table and ate, pretty as you please. From there, it was off to the Moorestown Mall and the multiplex to see X-Men: First Class which I thought was pretty darn good. When the movie ended and I left the theater, a stiff shower was in progress, and, not having an umbrella, I calmly stood and waited inside the mall for it to end. A few more people stared, but nothing more than that.

My next and final stop of the day was to the nearby Barnes & Noble where I would spend a solid twenty or so minutes wandering the aisles, but that time, I had been in the shoes for nearly five hours and they were feeling quite comfortable as they were breaking in rather nicely, I had gotten used to standing and walking after that initial period of acclimation, and, it was becoming fun too, the joy of discovering that maneuvering in five inchers wasn't as difficult as I thought it would be. That was my thought process as I headed back home, that five inchers were a world apart from what I was used to wearing, but I had successfully mastered the additional height with a goodly amount of on-the-job practice and I was loving the new shoes. And yes, I'll certainly wear them more often.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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For such a simple outfit, you really looked sharp. The shirt-jeans-heels combo was so casual yet you really looked cool. As one who is used to wearing 5" high heels on a regular basis, I guess that one inch heel differential would cause a little adjustment. I too am anxious to see the new X-Men movie and I am hearing nothing but good reviews. Congratulations on another successful jaunt and again, neat outfit.
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Just remember Jeff, That if you get too used to the 5 inchers your others will begin to feel like flats. It's actually best to keep changing heel heights. Looking good btw.

Shafted, the boots that is! View my gallery here http://www.hhplace.o...afteds-gallery/ or view my heeling thread here http://www.hhplace.org/topic/3850-new-pair-of-boots-starts-me-serious-street-heeling/ - Pm me if you want fashion advice or just need someone to talk to.

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roniheels: Thanks for the compliment. I appreciate it. Since it was a Saturday, I sought to put together an outfit that was both casual yet stylish. Yes, that added single inch was, in its own way, quite drastic, even dramatic. Oh, yeah, forgot to mention that wearing those five inchers was a bit tiring, having to maintain proper posture, standing and walking properly and all, but, yeah, I enjoyed wearing those pumps. Shafted: Yes, I've read that from other members, but I love my four inchers too much to give up on them. Heh!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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6/5/2011:

Today was my 100th jaunt since I began this thread, and, as I promised a few weeks ago, I wore my first dress to celebrate this particular centennial. Here's the whole outfit:

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A sleeveless black sheath dress with a matching patent belt from JCPenney, my gray men's Blazer (more on why I wore that shortly), L'eggs off-black pantyhose, the Pleaser "Vanity 420" pumps in black patent and my black leather handbag. I know I said I had dedicated myself to wearing only women's clothing on my jaunts, but I had ordered a women's blazer in gray from Penney's two weeks ago, but it's on backorder, and I wanted very much to pair that color blazer with my dress because of the stylish contrast. As for what the dress looks like without the blazer:

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By my own admission, the dress does look tight on me while emphasizng my shoulders, making them look broader than normal, and that surprised me since I ordered it in the largest size they had, that being 16, thus the desire to pair it with my jacket. And because of my height, it wound up being something of a minidress while on a woman say, five or six inches shorter than me, it would be knee length easily, but hey, I didn't mind since it gave me an opportunity to show off my legs which look good bare but are sensational with hosiery. So I was off to the western 'burbs to be seen and see what would happen. My first stop was to Borders in Springfield and I pulled into the lot some five minutes before the doors opened and there were over a dozen people waiting to get in, without a moment's hesitation, I hopped out and strolled right on up to the door, secretly thrilling to both the electric sensation of being in public wearing a dress and the sharp, solid clicking of the Vanity's four inch heels while wearing my usual cool, calm expression.

Nearly everyone gave me a glance as I approached, and more than a few eyes widened, but no one said a thing as the doors opened and we all entered. Once inside, I busied myself wandering the manga aisles to check for anything new, but there wasn't, so I retreated to the lounge area after buying a large cup of iced tea and broke out my nook™ and enjoyed a good hour and a half reading Sir Arthur Conan Doyle's The Lost World. People who entered the lounge area, everyone saw me, long legs and all, especially in that short skirt that was unintentionally hiked up as I sat, but again, there wasn't a peep from anyone. Around 12:30, I packed up my stuff, rose and headed for the door, just as I neared the door, a black woman who looked to be my age caught my attention, her eyes filled with curiosity and, in a near whisper, she asked if I was wearing a dress. I told her I was, she looked me up and down and said it looked good on me, even though I was a guy, adding, and I quote, "Honey, you've got balls to wear that in public! Love the shoes too!"

With a smile, I thanked the lady and went on my way, turning a couple more heads of drivers as I went to my car. To say the least, it was pleasantly surprising to have gotten a compliment on my attire, especially since I went into this jaunt thinking that wouldn't happen, but I was determined to go through with my nutty scheme anyway, just to see what would happen and what the reactions would be. While I got a few more stares and double takes than normal, I was able to go about my business. That was surprising too. But then, I purposely chose a bookstore where rowdy behavior would be all but non-existent, giving me confidence to undertake my little experiment. Wanting more exposure, I drove back into town and, stopping in the University City area, busy with college kids, I walked into a crowded Starbucks, pretty as you please, ordered a lemonade and retreated to the lounge area, sat and got in some more reading, Like in the 'burbs, I wanted to be seen, I wanted reactions, but got none, not even in Philadelphia proper. Imagine that.

All in all, it was quite a fun experiment, having pushed the envelope yet again by wearing a dress and living to blab about it here. Heh! In hindsight, I could've done better in choosing my dress, maybe bought a larger size that wasn't so snug or had so short a skirt, also, I should've added some jewelry like a neckchain or a pendant, still, I achieved my goal, and, for today, that was good enough for me. Do you think I was nuts to have done what I did? Perhaps, but I've probably done crazier things than this, so it doesn't matter in the end. In the meantime, I'll build on what I've done and strive to improve and do better the next time, should one come to pass. Does this mean I'll go out in a dress again? Maybe, because it had been thrilling, I won't rule out another venture in the future.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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All in all, it was quite a fun experiment, having pushed the envelope yet again by wearing a dress and living to blab about it here. Heh! In hindsight, I could've done better in choosing my dress, maybe bought a larger size that wasn't so snug or had so short a skirt, also, I should've added some jewelry like a neckchain or a pendant, still, I achieved my goal, and, for today, that was good enough for me....

You look good. The blazer length pairs well with the mini dress length. They also color coordinate well with each other.

Feminine Style .  Masculine Soul.  Skin In The Game.

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Wow, congratulations on a great 100th jaunt! I think the blazer makes for very elegant lines for the whole outfit, and it could just as easily have been worn by a woman who wanted to borrow a blazer from the mens section - maybe this worked in your favour as it's a good fit and blended your body shape comfortably into the overall look which is very coordinated and stylish. It'd be interesting to hear how the alternative blazer compares when it turns up. My impression was that the dress length worked great with those legs while the fit of the dress does look a bit snug around the shoulders/chest without the blazer but totally fine with it. I agree perhaps a simple accessory, maybe even just a watch, might have been a nice finishing touch. In any case the belt buckle added a nice sparkle.

If you like it, wear it.

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