The Jaunts of JeffB!

[JeffB]

8/17/2009:

Well, I was at it again with a brand new jaunt where I pushed the envelope once more. Here's today's outfit:

A patterned beige polo shirt from K-Mart, an 18 inch denim skirt from Old Navy, bare legs, the short strap handbag and my two inch heeled loafers. The aforementioned envelope pushing came from wearing my shortest skirt to date, and given that today was wickedly hot (expected high of 95), I wanted to see how it felt, given the heat. Stop number one was to a ATM a mile from home for cash, I thought I'd be a tad nervous wearing something this short, but I didn't feel any nerves as I calmly got out of the car, and got my money. Then it was off to the Post Office a few blocks away for a money order to pay a bill. Again, it didn't bother me to wait in line almost fifteen minutes while I was seen by customers and staff. I simply maintained a casual air as I conducted my business then left. Easy as pie.

Next up, another push by going to the Springfield Mall for a little stroll. Admittedly, it's not often that I walk through a mall in a skirt, especially one as short as I was wearing, but I decided to give this a try. However, it proved to have been an easy endeavor as no one gave me the time of day as I strolled through at a slow, leisurely pace, stopping in a Borders Express for a magazine, then Suncoast Video to check for new anime offerings, of which there were none. Then I strolled out, pretty as you please, actually forgetting that I was wearing a skirt, again, I simply had clothes on, and, despite the heat, I felt perfectly comfortable with my legs exposed. In a way, I actually amazed myself with how at ease I felt because it had been a breeze with no one giving so much as the time of day, boosting my confidence considerably.

Thirsty, I headed to the nearby Borders for a large iced tea which I enjoyed in the lounge with a couple of Mac-based magazines. Heck, I even sat and crossed my legs, mindless of how the short skirt hiked up around my thighs. I simply didn't care, and if anyone took notice of me, I didn't care about that either. I was relaxed, enjoying the cool drink and air conditioning and having a great time. From there, I head back home for lunch, pleased with myself for yet another successful outing in a skirt. And, having purposely worn a short skirt, I again felt emboldened, wearing what I wanted, not what society forces me to. It was an exhilirating experience as I went just a little further in my ongoing exploration into fashion freedom while validating what I've said time and again: wearing skirts are great fun!

[danielp6406]

Greatings JeffB :-)

8/16/2009: You described yourself perfectly when you said "well attired and looking sharp".

Could not agree more. And you were wearing the nice khaki skirt from Old Navy...

I didn't have a chance to go to Old Navy yet.

But looking at your picture, it was kind of a "reminder" that I must go shopping to Old Navy soon...

8/17/2009: A denin skirt also from Old Navy ?

Now I have two reasons to go shopping there

[Dawn HH]

JeffB:-) Fantastic outings all for you and your fabulous outfits very nicely co-ordinated as your usual. Maybe I'm old-fashioned, but I lean more to the outfits with the 4" heels than your 2" loafers. But that is just me. Chers--- Dawn HH

[Bootking]

Jeff, what is remarkable is that you look so natural in your alternate choices of clothing!!

[danielp6406]

Greatings JeffB :-)

I finally went to Old Navy and bought the blue denin skirt (Not the same but similar style)

Weather is really hot here. What a big difference wearing a skirt !

I received a call earlier from a neighbour: she was asking for help connecting her new sound system.

Guess what ? I didn't think twice and I went there wearing my new skirt !

She said the skirt was nice and I looked good in it. No negative comment.

Note that I was wearing flat sandals (She doesn't know I also wear heels...)

Again, you were right: It is only another piece of clothing after all.

Thank you for giving me the "inspiration" to wear a skirt !

So step #1 is done: someone else saw me wearing a skirt.

Step #2: Will I wear it in public ? (to the shopping mall or maybe to work)

I guess I will try the shopping mall first (wearing flats) to see how I feel then I will decide ...

Maybe step #3 will be wearing the skirt with heels ? (Who knows...)

Happy heeling and happy skirting all !

[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!