The Jaunts of JeffB!

[JeffB]

Thanks for the kind words, everyone! Much appreciated! danielp6406: Congrats on your purchase, and your little outing in your skirt with the neighbor. Wasn't as terrifying as you thought it would be, was it? As for your next outing, hey, no big deal about wearing flat shoes with a skirt, if you feel that works best for you, then, by all means, go for it. Good luck, my friend!

[tallguyinheels]

danielp: Actually my thoughts are that if you were somewhat comfortable "skirting" with your neighbor, then out in places where you are not likely to be recognized will be a piece of cake!

[danielp6406]

Greatings JeffB and tallguyinheels :-)

In order not to "hijaak" JeffB's thread any longer, please see my reply here > http://www.hhplace.org/general_fashion/13934-bought_skort-3.html#post215422

[JeffB]

8/21/2009:

Went on another entertaining outing on Friday. The theme for my outfit that day was casual, well casually dressy anyway:

A navy polo shirt from JC Penney, my favorite 22 inch denim skirt which I've come to love and wear more than any other, bare legs, my short strap handbag and Payless "Judy" pumps which I had just bought a couple of days before my outing. Here's a close-up:

A stylish shoe with a rounded toe, three inch heel and a bow on the vamp. And the shoes were quite comfortable too! If you're not put off by the bow, giving the shoe a decidedly feminine look, you should buy a pair. Anyhoo, my first stop was to my favorite downtown comic shop which had nearly a dozen customers, but no one paid me a moment's notice. Next up was lunch and a place I hadn't eaten at for months: Pizza Hut! I went to the store in the western burbs where I was treated like any other customer as the store was I'd say about a quarter full. I had the buffet and ate my fill, perhaps a little over my fill, but hey, nothing wrong with a little indulgence every now and then. Heh! However, I got a little surprise when I went to the register to pay my bill, the girl who waited on me grinned and said, "Nice shoes". I grinned and told her thanks.

Stop number two was Borders,now my regular heeling/skirting hangout. It too was fairly packed for a midday, but that didn't bother me as I ordered a large iced tea and relaxed in the lounge with a couple more Mac magazines for little over an hour. After Borders, I planned to swing by Best Buy, but the weather had gone to hell as a violent t-storm blew through, so I changed my mind and went home. Despite how short my outing was, I was very pleased at how comfortable I felt the whole time, it didn't register to me that I was wearing a skirt and heels, I was simply wearing clothes and shoes that I felt at home and at ease in, and that's the important thing, the comfort factor. I'm also amazed at how far I've come in my freestyling, at how a skirt and heels has become commonplace for me, and I enjoy that feeling most of all.

[LovesHiHeels]

Those outfits work well on you. The denim skirt and the low heels seem to work well on a male.

[JeffB]

8/23/2009:

With a sunny Sunday staring me in the face, I decided to go on yet another casual S & H (skirt & heels) outing, but I switched up the routine in order to keep things fresh. And here's my outfit:

A brighter blue polo shirt from JCPenney, my now well known 22 inch denim skirt, bare legs, my short strap handbag and, for a second straight jaunt, the Payless "Judy" pumps which I've quickly come to enjoy wearing for the comfort, moderate heel height and cute style. Today's trip was over into south Jersey with my first stop being Barnes & Noble for a light lunch consisting a large pretzel stuffed with cheese and pepperoni along with an iced tea while reading the Sunday paper in the lounge area. As was usually the case, I didn't draw any attention since I considered myself dressed down but tastefully for the day. I think I was there for close to an hour, but when I left for stop number two, it was already sticky, however, thanks to the skirt, I felt quite cool while the pumps were as comfy on my feet as my favorite pair of sneakers.

Stop number two was to the nearby Moorestown Mall where I went to see Quentin Tarantino's latest flim, Inglorious Basterds. Cool and collected as could be, I strolled up to the box office (the only negative to the "Judy" pumps is that the heels don't make nearly enough noise to suit me), bought my ticket and strolled on in, ignoring the odd turned head here and there. As for the movie itself, it was good, but nowhere near as great as Pulp Fiction. I don't know if Tarantino will ever be able to equal what I consider his masterpiece, but that's my opinion. Two plus hours later, I left the theater and strolled to the food court for something cool to drink before heading off to Best Buy, my second home for some gadget gawking. So sue me, it's a pleasant weakness, sorta like wearing women's clothing and shoes. Heh!

While in the big screen TV section, I noticed a fellow watching a trailer for, ironically enough, Inglorious Basterds, I walked up to him and mentioned that I had just seen the film, looking interested, he asked what I thought of it, I told him it was good, but not close to Pulp Fiction, he nodded, saying Tarantino has slipped some since PF, something I agreed with. We spent a good couple of minutes discussing IB, told him it was a little long but that I thought it was worth the time, he thanked me then left. Don't know if he noticed what I happened to have been wearing, but he was more interested in talking about movies. Pretty neat if you ask me. Now, I do think I heard a giggle during the time I was in the store, not to mention a couple turned heads and double takes, but I'm long used to those sort of reactions from people.

All in all, another great jaunt, one I was quite pleased with personally. I guess I'm getting the hang of wearing skirts and heels, especially since it's all I've worn on my freestyling adventures since November. Hard to believe it's been that long now, and, in some ways, I feel that I'm just scratching the surface as I continue exploring this strange new frontier. And, it certainly goes without saying that I'm having a great deal of fun as well.

[roniheels]

JeffB...

Once again, congratulations on another successful and fun outing. you continue to inspire all of us here at High Heel Place.

[Bootking]

As I said before, it looks just plain good and natural!

[JeffB]

roniheels & Bootking: Thanks for your kind words. I appreciate the comments. I do as best I can to both inspire, and have fun at the same time.

[danielp6406]

JeffB :-)

I agree with Bootking: "it looks just plain good and natural"

And your black pumps looks much better than my flip-flops ....

[HappyFeat]

Great outings Jeff! I have been rather busy and have limited Internet access at the moment, so I have not been able to keep up to the level that I typically like to. However, all of your recent outings were great reads and looked very nice. I think you have found the style that works best for you and what is better than that? I really liked the black skirt/green shirt combo with the pumps. And I agree with you waitress wholeheartedly...nice shoes! Glad to see you have been getting out a lot recently.

[JeffB]

danielp6406: Thanks for the kind words on my shoes. I like to look stylish, and those pumps certainly qualified in my mind. HappyFeat: Welcome back, my friend. Glad to read that you enjoyed my most recent outings. Yeah, perhaps I have found my stride when it comes to my particular style, and it does look good on me, however, I haven't given up on trying out a dress, and I think I can make that work too.

[HappyFeat]

I am still waiting to read about (and see the pictures, of course) of you wearing a dress. I didn't want to bring it up, because I don't want to offer "peer pressure" but I think you will love it beyond words. And, most defiantly, you would pull it off great. Keep experimenting my friend, but know that you have one fan eager for the first "dress outing!"

As for Terintino, I don't think its fair to compare any of his other stuff to Pulp Fiction. Forrest Gump may have won the Oscar, but Pulp Fiction is the classic movie of the 1990's. It is simply a masterpeice of dialogue and innovation. That being said, my favorite Terintino flick is Jackie Brown, though it is an adapted novel. But maybe I am just in love with Pam Grier. And lets not forget, Dusk till Dawn revived Cheech Marin's career, which is quite the cultural contribution in my mind.

[JeffB]

I am still waiting to read about (and see the pictures, of course) of you wearing a dress. I didn't want to bring it up, because I don't want to offer "peer pressure" but I think you will love it beyond words. And, most defiantly, you would pull it off great. Keep experimenting my friend, but know that you have one fan eager for the first "dress outing!"

Oh, no! No "peer pressure" at all, my friend! Like you said, I most definitely WANT to wear a dress on a jaunt, just to see what it would be like. I think it would make for a great experience, one I'm looking forward to once I find just the right dress which so far, has proven to be a tad more difficult than I thought, but I'm still out there looking.

As for Terintino, I don't think its fair to compare any of his other stuff to Pulp Fiction. Forrest Gump may have won the Oscar, but Pulp Fiction is the classic movie of the 1990's. It is simply a masterpeice of dialogue and innovation. That being said, my favorite Terintino flick is Jackie Brown, though it is an adapted novel. But maybe I am just in love with Pam Grier. And lets not forget, Dusk till Dawn revived Cheech Marin's career, which is quite the cultural contribution in my mind.

Quite right. It would be unfair to compare one flick to another, but I loved Pulp Fiction so much when I first saw it, I sorta became spoiled because of it's magnificence, especially since it really launched the career of Samuel L. Jackson who's one of my all-time favorite actors. I also tend to compare any Bond flick that followed Goldfinger as somewhat lacking instead of appreciating each film on it's own merit. But hey, that's just me. Heh!

[JeffB]

8/27/2009:

Another day, another outing, another opportunity to have some fun while out and about. Today, I put a little color into my footwear as evidenced by the photos below:

My dark red JCPenney polo shirt, black Old Navy skirt, bare legs, my short strap handbag and the Payless Lance Flex pumps in merlot. This made the third time I've worn these pumps in public and I continue to marvel at how awesomet these shoes are, mainly for the color. It normally feels great to wear pumps (especially with a skirt), but to wear these dark red shoes is doubly delightful. Stop number one was to Best Buy, I arrived a little after 11 a.m., so the store wasn't too crowded, however, I did garner a couple of looks here and there, I spent a good fifteen minutes chatting with a sales associate about the relative merits of LCD versus Plasma hi-def TV's, learning all I could as I'm thinking about upgrading my current set, and the salesperson never blinked an eye about my eclectic outfit, and, acting casual, I never gave him reason to.

After buying an anime DVD, it was time for lunch as it was close to noon and my stomach was demanding attention. I drove west to a strip mall and Subway, one of my favorite lunchtime hangouts. Walking in, there was a bit of a line and a couple more people stared briefly, I suspect they, like the glancers in Best Buy were taking notice of the shoes. I guess they never saw a guy wearing red pumps before. Whether or not they paid any attention to the skirt or the handbag I have no idea. Minding my own business, I placed my order, paid for my meal and sat down like every other customer to eat and read the paper while people filed past. I ignored them. For me, there was no other way to handle things, as is always the case during my jaunts, I just act normally, like it's no big deal to strut around in heels and a skirt, because it's not.

Stop three was to my other favorite hangout, Borders. For a third time, the shoes attracted a double take was I walked towards the store, once inside, I went about my business of enjoying a large iced tea in the lounge area with a few computer magazines, relaxing like everyone else, even though a guy sitting ten feet from me in another chair stole brief glances every now and then at me. But hey, it was no big deal for me, still, it was, interesting to have been noticed like I had. Again, it must be the shoes. Imagine if they were fire engine red! HA! All in all, it was another fun filled outing for me as I'm growing more and more comfortable in a skirt and heels during my jaunts. This is quite an exciting time for me in my ongoing fashion freedom exploits.

[Bubba136]

Wow! What a great look Your outings are just great. By the way, thinking back a few years to the time that you used to post pictures of yourself in your cubical at work, do you still have any of those great pumps that you used to wear? I remember a picture of you wearing a pair of bright red pumps with a white shirt and blue trousers (or, some combination of red, white and blue). Those pictures were really great, too. They really showed all of us how much care you took to put together just the right outfit. And, it appears that you still exercise the same skill, today.

[tallguyinheels]

Casual and competent... that's how you look and act... I just am starting to appreciate the attitude required to not be concerned with the looks and attitude of other toward less conventional male dress and footwear.

[JeffB]

Bubba136: Ahh! The good old days! Heh! That pic you mentioned was something I did as a joke just before the Fourth of July as I wore red (shirt), white (pumps) and blue (pants) at the office. Gotta a few chuckles from co-workers who got the joke if memory serves. Yep, I certainly did my very best to look my best when in public, and I still do to this day. There's no other way to do this sort of thing. tallguyinheels: Thanks for the kind words. That attitude didn't develop overnight, it took time for me to build up what everyone sees as a casual demeanor. It can be done, but not right away.

[Bubba136]

JeffB: You really had some great pairs of shoes back then. I hope you still have some of them in your closet. But, the most impressive thing about your wearing heels back then is that you had the courage to openly, without any the slightest pause or hesitation, wear your heels to your government job in front of all of your workmates, for the entire working day and even wearing them to lunch in the cafeteria. I remember thinking how courageous you were (and still are).

[JeffB]

But, the most impressive thing about your wearing heels back then is that you had the courage to openly, without any the slightest pause or hesitation, wear your heels to your government job in front of all of your workmates, for the entire working day and even wearing them to lunch in the cafeteria. I remember thinking how courageous you were (and still are).

Ahh! Those certainly were the good ol' days! I'm glad folks like you appreciated those early adventures, and yeah, it sure took lots of guts for me to have done what I did back then, I know I had fun, and, in a way, those daily exploits helped me evolve to where I am today, so that's a good thing.

[JeffB]

9/6/2009:

A new month, a new outing for yours truly as I enjoyed a new round of freestyling and the delights of being seen by the world at large. Here's what I wore on my latest jaunt:

A beige polo shirt with a zipper instead of buttons, my favorite Old Navy 22 inch black skirt, bare legs (of course), my short strap handbag (of course) and the Payless Lance Flex pumps in black. I've come to really enjoy my skirt and pumps combo which I think is really flattering on me, so any chance I can get to trot out said combo is a welcome one. The weather was sunny and comfortable as I drove out to the western 'burbs, my first stop being Subway for lunch. As I walked to the door, a father and his young son came from another direction and we sorta met at the door. Both looked me up and down (guess they never saw a guy in a skirt and heels before) but said nothing as I opened the door and, with a nod, I let them in first. I stood patiently in line behind the couple as the father placed the order and the son stole a glance or two at me.

As it turned out, the couple decided to eat in, just like me, so we were seated some ten feet apart. I paid them, especially the kid no mind as I ate, I'm sure the kid must've been flabbergasted and wanted to say something, anything, but the dad wouldn't let him. No big deal. The couple left after some fifteen minutes (a bit hurriedly in my opinion) and I was left alone to finish my lunch, chuckling inwardly at dad and son. Stop two was to my regular hangout on my jaunts, Borders. While there was a parking spot close to the store, I intentionally parked a good hundred feet away instead. Why? Vanity, I wanted to hear the heels clicking as I walked to the door, plain and simple. As I approached the store, I cold see my reflection in the storefront and I grinned because of how good I looked, then put a little sway in my hips as I walked and I grinned more.

Once in the store, I did notice a turned head or two here and there as I wandered the aisles, picking up the latest issue of Macworld and a couple of Brit based mac mags to read in the lounge area with a large iced tea and I relaxed with my reading material just like every other customer, spending close to an hour there as is often my want, as usual, a pleasurable little slice of heaven. I can understand why so many people spend so much time in places like Starbucks and in-store coffee shops. It's great. And all the while, it never occurred to me that I was wearing a skirt and heels, I was simply wearing the clothes that I feel comfortable and at ease in, the fact that said clothes and shoes are worn more by women than men was of no consequence to me. It's only small-minded people that obsess over assigning gender labels to clothing.

These last several months spent expanding my horizons when it comes to fashion freedom has been absolutely exhilirating to me. I never knew just how enjoyable it's been to wear skirts with my heels on a regular basis on my jaunts, admittedly, I can't bring myself to wear anything else, I don't even look at my jeans or pants these days, and I don't mind that at all as skirts are more fun. More adventures to come!

[stefan]

Jeff, Yet another very nice outfit and story. I really love reading them. That is an inspiration to us all. Keep up the good work man. /Stefan

[Mr. X]

Way to go Jeff! Looks like you are truly "working" your outfits. Isn't it funny how our mindset changes as we get more comfortable in our outfits and shoes. You mentioned how you intentionally parked far away. Now if that had been you first outing I guarantee 100% that you would have taken the close spot. And you would have done everything in the world possible to cover up and hurry into the store as fast as humanly possible. I am by no means at you level of dress yet with the skirts and pumps. Not that I necessarily even want to venture into such territory. But the point I am making is that when I wear my boots, which is my heel of choice most of the time, I am truly comfortable in them now. I don't even give them a second thought. I am at the point where not only do I not try to cover them up but I even try to present opportunities for them to be seen. Things like standing a certain way or raising my pants just a little to expose more of the heel. It is a level of comfort that is magical to us when it is reached. And it appears that you are at that level with your skirts and pumps. Again, way to go!

[Thighboots2]

Jeff, Your fast becoming the new "Dale Miller". Simon.

[JeffB]

stefan: Thanks for the kind words. I'm glad that I can be an inspiration to others here. Mr. X: You couldn't be more right! A year or so ago, I wouldn't have had the nerve to be so bold like I am today. Some days, I amaze myself with the brazen things I do, but hey, it's fun and that's what matters most for me. Don't worry about not being able to follow in my footsteps, in fact, you shouldn't if that's not your bag. The important thing is to be comfortable in your own skin and go your own way instead of following others. Do what you want and enjoy yourself in the process. Thighboots2: Wow! I consider that high praise indeed! Thanks!

[Thighboots2]

Jeff, Well I see a lot of similarities, although I prefer the plainer skirt. Dale always seemed to be pictured in pleats. Not really sure he had the legs for shirts either. Perhaps you should try the skirt suit look, as our friend in NZ, Heel-Lover has done. That may be an interesting look and one that you may well carry off well. It may take a bit of courage to go that next step, but it could look very good indeed. You do not seem to overdo the height of the heel, and that to me is key. High heels, stiletto or otherwise, smack of fetish regardless of gender, and as you are moving trying to move the goalposts, avoiding that label is key. So far, I don't see anything you have done as attracting that label, but if I did, then I would say so. Simon.

[HappyFeat]

Yet another fantastic outfit. In my opinion, for what its worth, it may be your best look yet. It is classic, a bit dressier, but still casual enough for a day out. Which leads me to the thought of people have taken casual to mean "sloppy" in my opinion. I think that more people need to dress smarter even when going out for a casual day. I too appreciate your parking far way to enjoy the stroll into Borders. I wouldn't call it vanity however. Empirically you looked great. Its your obligation to share that with the world. If you have gone to the same one on many of your outings, you should be fast becoming a local celebrity! Thighboots2 gives you wonderful advice about a skirt suit. You would look smashing. Recently I went to a Kasper outlet, which is a Donna Karen (I think) line of low end business suits. I tried on a couple of skirt suits and a couple of pants suits and was shocked at how great I looked. At the outlet and being the end of the season, you can find a decent skirt suit for minimal investment. Now that Labor Day has passed, the sales should really begin to pick up and I plan on going back for a suit to wear later this fall when I shave again. Of course, there is the issue of getting a skirt that fits with a jacket that will fit with a man's shoulders, however, if you get a suit with 3/4 length sleeves, it will kind of balance out the size/fit issue. The only down side to a suit is finding a place to wear it. Personally, I would wear it on an outing like you just had, but some people might be uncomfortable because of being over dressed. Anyway, it is worth thinking about because I think you would pull it off great!

[Thighboots2]

Here in the UK we have "high street" retailers who do both mens and womens suits in the same fabrics (I'm sure you will have similar retailers in the US). This way you can obtain a mens jacket and a matching skirt from the womans range. Personally, I would go for a knee length skirt rather than over knee. Too short and it will look wrong. I also liked Heel-Lover's use of a waistcoat. I just felt his choice of skirt was too short, but that is a matter of my opinion only. You should steer clear of jackets for women because your man shape torso is just wrong for the cut. You are investigating the juxtaposition of male/female clothing in general anyway, and this is just a more formal example. Ladies suit pants, if you want to try these too, work so much better with heels than mens pants do. The slightly bigger cuff just sits better over the shoe. I do like the cuff on ladies pants anyway just for the freer look and how it hangs so much better, even with regular shoes. Do you have a nice leather messenger type bag? I think I would prefer to see you use that rather than those I have see you in the pictures. Again this is becuase of the juxtaposition of gender identity clothing you are working with. Having a male head poking out too much of a feminine look doesn't quite work for me. You do not need to cloud the masculinity statement with too much femininity. A delicate balance indeed. Simon.

[danielp6406]

Greetings JeffB :-)

Another very nice outfit. I like the color combination.

I agree with others: This may be your best skirt outfit yet.

[JeffB]

Thanks for the responses, everybody! As always, I appreciate the comments!

You do not seem to overdo the height of the heel, and that to me is key. High heels, stiletto or otherwise, smack of fetish regardless of gender, and as you are moving trying to move the goalposts, avoiding that label is key.

As a rule, I never go over four inches since I do a goodly amount of walking while on my outings, and comfort is quite important to me. Besides, exceeding four inches in purely casual settings just doesn't work and would make me stand out, as if I don't already. HA!

Yet another fantastic outfit. In my opinion, for what its worth, it may be your best look yet. It is classic, a bit dressier, but still casual enough for a day out. Which leads me to the thought of people have taken casual to mean "sloppy" in my opinion. I think that more people need to dress smarter even when going out for a casual day.

I quite agree with you. Too many people have taken to equating "casual" with "sloppy", as if they just don't care how they're seen while in public. Like women with rollers in their hair or wearing what looks disturbingly like pajama bottoms, not to mention those damnable flip-flops EVERYWHERE! As for me, it's somewhat difficult to dress down while on my jaunts, even in a casual setting because I want to look my very best while out and about in heels and a skirt, and, admittedly, that makes feel just a wee bit self-conscious about being overly dressed for my surroundings.

Perhaps you should try the skirt suit look, as our friend in NZ, Heel-Lover has done. That may be an interesting look and one that you may well carry off well. It may take a bit of courage to go that next step, but it could look very good indeed.

Thighboots2 gives you wonderful advice about a skirt suit. You would look smashing. Recently I went to a Kasper outlet, which is a Donna Karen (I think) line of low end business suits. I tried on a couple of skirt suits and a couple of pants suits and was shocked at how great I looked. At the outlet and being the end of the season, you can find a decent skirt suit for minimal investment. Now that Labor Day has passed, the sales should really begin to pick up and I plan on going back for a suit to wear later this fall when I shave again.

I have given considerable thought to the idea of a skirt suit, and, at the risk of sounding vain, I agree with both of you that I probably would look great in such an ensemble. I've searched a few resources and have seen some nice offerings, however, in almost every instance, the skirts were too damn long, falling to the knee. Kill that noise! If I were to buy a suit, I'd definitely HAVE to have the hem shortened so I can show off my legs. But seriously, the one thing that's stopped me from buying a suit is the question of where I would wear it and not stand out in whatever setting I'm in as it's WAY too dressy for casual locations like bookstores of malls. I'd have to give a whole lot of thought about where I could wear a suit and not look odd.

Ladies suit pants, if you want to try these too, work so much better with heels than mens pants do. The slightly bigger cuff just sits better over the shoe. I do like the cuff on ladies pants anyway just for the freer look and how it hangs so much better, even with regular shoes.

Pants?? YUCK!! No way, Jose! Homey don't do pants! Skirts all the way!

Do you have a nice leather messenger type bag? I think I would prefer to see you use that rather than those I have see you in the pictures. Again this is becuase of the juxtaposition of gender identity clothing you are working with. Having a male head poking out too much of a feminine look doesn't quite work for me. You do not need to cloud the masculinity statement with too much femininity. A delicate balance indeed.

Hmm! Interesting! I must say your idea does bear investigating! Thanks for the suggestion!

I too appreciate your parking far way to enjoy the stroll into Borders. I wouldn't call it vanity however. Empirically you looked great. Its your obligation to share that with the world. If you have gone to the same one on many of your outings, you should be fast becoming a local celebrity!

That was one of those rare instances where I let my ego have free reign and I openly showed off. I felt so good at that moment because I looked good, I simply wanted to flaunt, and that felt good too! Again, it's all about the incredible amount of fun that comes from wearing heels and a skirt. As for becoming a celebrity, well, I don't about that quite yet! HA!

Another very nice outfit. I like the color combination. I agree with others: This may be your best skirt outfit yet.

Thanks! I simply do as best I can.