The Jaunts of JeffB!

[JeffB]

Thanks for the kind words! 

[Steve63130]

Well, if I can chime in here, I appreciate what BOTH of you have done to serve our country. Freedom isn't free, so I am grateful for what you've done to protect my freedom, including my freedom to wear heels. Not that I planned it this way, but I do happen, by coincidence, to be wearing NAVY sandals - White Mountain Shoes' "Terrace" sandals with 3.5" dark cherry faux wood grain heels!

Thanks again!

Steve

 

Edited August 11, 2016 by Steve63130

[bluejay]

Nice looking sandals, Steve. As I have the same style in black and tan, I wanted to get the navy color too. Unfortunately they did not have it in my size.

Happy Heeling,

bluejay

[SkirtDude]

Great outfit, Jeff! I am changing over to casual denim skirts rather than the usual formal business ones. You always look so composed in your outfits. Looking forward to your next jaunt

[Thighbootguy]

JeffB;

The numbers are great but they give a misleading picture.  Try running the numbers for just 2016 and I think it will give a completely different picture of what your wearing and point out that your thigh boot wearing has been woefully neglected. 

[RonC]

Just curious, Steve - do they slim the leg as advertised?...lol

[Steve63130]

Ron,

Not that I can tell. Marketing hype if you ask me. But they're fun to wear, very stable, easy to walk in, and good looking, in my opinion, so I'm not about to part with them!

Steve

[JeffB]

On 8/15/2016 at 0:40 PM, Thighbootguy said:

JeffB;

The numbers are great but they give a misleading picture.  Try running the numbers for just 2016 and I think it will give a completely different picture of what your wearing and point out that your thigh boot wearing has been woefully neglected. 

Hmm! You may have a point there. I'll see about correcting that oversight come fall. 

[JeffB]

Jaunt #326, 8/22/2016: The one thing about summer that I don't particularly like is how the extreme heat that visits every so often makes me so lazy, I don't want to go on any jaunts, with seemingly every day over the last two plus weeks in the 90's with gagging humidity, I just couldn't muster the energy for an outing until today as a cold front that blew through yesterday with rain and a thunderstorm in spots knocked down the temps to something more manageable for an outing today as I headed out in a blue tank top, a 19 inch white denim pencil skirt from Old Navy, the Payless "Stacey" low wedge sandals in white and a bag to match.

Now, in the sake of full disclosure, I must admit that I felt a wee bit of anxiety going out in a white skirt, something I had only done once before, and that was something like three or four years ago, there's two reasons for that, one, it stands out (like I should worry about that), two, I worried about getting it dirty, still, like practically every skirt I've worn over the past several years, it looked good on me, so I was eager to take it on a spin. Meanwhile, my summer passion for shoes I once swore I'd never wear continued unabated, last summer it was my fling for those "O'Malley" platform slides which I fell in love with, this year, it's my craze for sandals, especially flat (or relatively flat) sandals, and the Stacey shoes with their cute styling and 1 1/2 inch wedge heels that attracted my attention and have been at the head of the queue. As for the outing, I headed west into Springfield, my first stop being to Home Depot to buy some weed killer to keep my small front yard from being choked with that crap which is always a pain in my neck at this time of year, from there, I went to the nearby Acme next door to buy a couple of odds and ends, then to Arby's not too far away for lunch. The longer I was out and about, the more relaxed and at ease I felt, particularly after I left I left that fast food joint with my skirt unsoiled.

After I ate, it was off to center city where I haven't been on a jaunt for awhile. It took nearly half an hour to find a parking spot, after I did, I headed to Rittenhouse Square Park to chill out for a time with my nook e-reader. While at a corner waiting on the light, a twentysomething young lady looked me up and down, grinned, then said, "I'm sorry to stare, but you've got great legs. Heck, you look better in that skirt than some women I know. And I love your sandals!" I grinned back and thanked her before we went our separate ways. It had been some time since I had been complimented on my attire, and today, I got perhaps THE ultimate compliment, that I looked better in a skirt than a woman. Wow! That was something! Once again, I guess that meant I did something right, that presentation was good enough to warrant that sort of compliment. It makes everything I do, all the time and trouble I put into looking my best for my outings worthwhile. What that young lady said stuck with me the whole time I was in the park, let me state that everyone reading my words should do the same, work as hard as you can to look top notch, it'll be worth it in the end. More to come....

 

[Thighbootguy]

JeffB;

The white skirt looks great and the white bag adds balance to the whole look.  I will admit when I read you description of your outfit (without scrolling down to the pictures) I thought a white skirt would be too much contrast to your skin tone but I was wrong and it looks great.  I'd even suggest a white light weight blazer with the blue top to enhance to look.

3 hours ago, JeffB said:

The one thing about summer that I don't particularly like is how the extreme heat that visits every so often makes me so lazy, I don't want to go on any jaunts

It is amazing how well couch potatoes thrive in conditions of high temperature and humidity.

[Steve63130]

8 hours ago, JeffB said:

 

I headed west into Springfield, my first stop being to Home Depot to buy some weed killer to keep my small front yard...

 

 

Jeff,

You're going about it the wrong way. Don't use poisons. Get a pair of these and stomp the weeds to death. Much more fun!

That's why they call them "killer heels!"

LOL

Steve

[SkirtDude]

On Tuesday, August 02, 2016 at 9:50 AM, JeffB said:

18 hours ago, JeffB said:

Jaunt #326, 8/22/2016: ...

After I ate, it was off to center city where I haven't been on a jaunt for awhile. It took nearly half an hour to find a parking spot, after I did, I headed to Rittenhouse Square Park to chill out for a time with my nook e-reader. While at a corner waiting on the light, a twentysomething young lady looked me up and down, grinned, then said, "I'm sorry to stare, but you've got great legs. Heck, you look better in that skirt than some women I know. And I love your sandals!" I grinned back and thanked her before we went our separate ways. It had been some time since I had been complimented on my attire, and today, I got perhaps THE ultimate compliment, that I looked better in a skirt than a woman. Wow! 

Looks fantastic, Jeff! I have been avoiding white skirts for the same reason   I do have a khaki pencil skirt but that's as daring as I'm going to go  

For some reason the reply function is not working so excuse the re post or quote. 

You do look great in your ensembles, a look I am working towards as well.

Lookingforward to your next jaunt  

[bluejay]

Great look JeffB!!!!!!!!!!!.

I like wearing white skirts and white shorts which I've been wearing a lot this summer. Yes, you have to watch yourself while wearing white, but I love the combo with brightly colored tops in royal blue, red, fuchsia and several other colors that I have. I get lots of compliments from the ladies, especially wearing white heels or white sandals. Sometimes I like to match my shoe color with the color of my top, I'm wearing. And yes, I always carry my cross body bag in a color to match my shoes.

Keep up the great looks.

Happy Heeling,

bluejay

[JeffB]

TBG: Thanks for the kind words. I've probably said this before, but I do a great deal of experimenting with tops, skirts and shoes and take notes on outfits I put together. As for a blazer to match the skirt, I'll see if I can find one, but, with Labor Day getting closer, I might have to save that for next year. Lastly, being a couch potato can be fun! HA!

Steve63130: A co-worker would call such shoes "Roach Killers" because the pointed toes are effective in skewering the little buggers, especially in corners. Heh!

heelsrus2000: Thanks for the compliment. Much appreciated. Wearing white can be rather adventurous. I strongly recommend it. I'm sure you'll enjoy the experience.

bluejay: Thanks for the kind words. The key to wearing a white skirt is a brightly colored top. I don't have one in fuchsia, but I'll see about finding one.

[Mr. X]

Looking good Jeff!  That blue and white combo is killer!  it is one of my favorites color combos as well!

Edited August 25, 2016 by Mr. X

[JeffB]

Thanks for the kind words, Mr. X. Much appreciated.

Jaunt #327, 8/26/2016: I really don't know why it is, but every time I've visited the Philadelphia Art Museum on a jaunt, I've dressed up for the outing. I guess I feel the need to need to look classy for when I immerse myself in culture, and today's trip there was no different as I wore a satiny black top with embellishment on the sleeves, a knee length, black printed skirt, a black handbag, my strand of pearls and the Payless "Karen" peep-toe pumps. Beyond the fact this was the first time I've worn pumps in goodness knows when (and I'll admit it felt a tad strange after weeks of slides and sandals), this was the very first time I've worn peep-toe shoes, but the combination of that, the ornament on top and the four inch heels made those shoes a delight to wear because of their snazzy styling. All together, it made for a dynamic ensemble I enjoyed wearing. As I've stated in another thread, I look great in women's clothes, and today's outfit was further verification of that claim.

I arrived in the museum parking garage at eleven a.m. sharp, and once inside the building, I saw right away there was a considerable crowd, especially kids what with their being on vacation, yet no one gave me the time of day as I waited in line to buy my ticket. Even though I've been in the museum several times now, I never failed to be amazed with the incredible works of art I see there, American, European (going back to the 1100's), Asian, contemporary, and my favorite area, the hall of armor and weapons, I find that to be particularly cool. Going from area to area, passing by young and old, getting not even a glance, I enjoyed all the sights at a casual pace, I even chatted for a couple of minutes with an older couple about a large piece of art from the 1700's where the artist himself was part of the scenery. The only problem with being at the museum is that it's practically impossible to see everything in just one visit, even after a four hour stay, but, I find that to be a good thing as that gives me an excuse to go back to see more, and to dress up for the trip like I had today. More to come....

[Thighbootguy]

Again well done JeffB! Even though I have been following your adventures for years and I have some idea what to expect when I scroll down the page to see your pictures, my first impression today was not a guy dressed as a woman, rather, I saw a middle aged woman.  I recognized you face as JeffB, but when you presented yourself to a stranger it might take them a while to recognize that they weren't seeing a female.  I repeat, well done JeffB, the outfit looks great..

I really am glad you are enjoying the museum.  I haven't been over to the Cincinnati museum for a long tome and I will have to remedy that situation.

[SkirtDude]

It's a nice skirt but with the top and necklace I too saw a woman with short natural hair. I think the pencil skirts in denim / khaki give off a better look as a guy.

Still, looking forward to your next jaunt

Edited August 28, 2016 by heelsrus2000

[JeffB]

TBG: Well, that was an interesting observation, seeing me as a middle aged woman in that outfit I wore. Anyhoo, thanks for the kind words.

heelsrus2000: Denim is okay, but I like to wear dressy skirts from time to time as I don't worry about what looks good or not on guys.

Jaunt #328, 8/27/2016: I feel that every outing I undertake is a new chance to practice my version of self-expression as a fashion freestyler, not to mention experimenting with different sort of looks to see what works and what doesn't. Even though it was a wee bit sticky and humid, I still went out, garbed in a black tank top, a printed crinkle skirt, my latest footwear acquisition, the Payless "Tawny" crossband slides and a black handbag. The new shoes with their three inch wedge heels were stylish, comfortable and, like the O'Malley slides, were easy to wear and comfortable to stand and walk in. Hard to believe that just a few short years ago, I wouldn't have been caught dead wearing slides, now they're a big part of my summer footwear routine. Meanwhile, the top and skirt made for a good combination that was enjoyable to wear.

My first stop of the day was to convenience store for a newspaper and a Powerball ticket, the person who waited on me, an Asian woman in her late twenties who said she liked my necklace, I smiled and thanked her. From there, I headed to my favorite downtown hangout, Rittenhouse Square Park, as usual, the place was packed on a sunny late Saturday morning and I wandered through until I found a bench under a shady tree where I sat and read my paper while people came and went, as usual, it felt good to be treated like every other person who was enjoying the nice weather in the park, proof of acceptance for my presentation, and that's certainly a good thing as far as I was concerned. After an hour spent reading and enjoying the surroundings, I returned to my car and drove over into South Jersey, stopping at a multiplex across from the Cherry Hill Mall where I took in the latest Jason Statham actioner, Mechanic: Resurrection which wasn't too terribly bad. Other than getting a couple of stares from young kids, it was an uneventful trip to the movies.

From there, I went to Moorestown as I had a hankering for a Chick-Fil-A chicken salad sammich, even though the lines were long at the store, it was worth waiting for, and more as that's tasty stuff indeed. Other that a couple more looks here and there, I wasn't bothered while I ate. My last stop of the day was to Barnes & Noble for a little quiet time, as I approached the store, a black lady a little older than me coming out the store smiled and said, "That's a pretty skirt, young man. You wear it well." Being called a young man was an even nicer compliment than the kind words on my skirt, I broke out in a big grin and thanked her. I would spend an hour in the store reading several football magazines while nomming on an oversized cookie which was majorly delicious. All in all, it was yet another enjoyable outing, but then, that's par for the course, though I never take anything for granted, every chance I get to wear women's clothes in public is always fun and pleasurable. More to come....

 

[Thighbootguy]

Well done young man, well done. 

I know you keep saying " I don't want to LOOK like a woman, I just want to DRESS like a woman!", but I do think you're starting to LOOK the part. I think it is that the outfits you are assembling fit my stereotyped image what a woman would be wearing, which means you are meeting your goal, but once that "woman image" is triggered in my head I have to work at the extra thinking to realize I'm wrong and the image I'm seeing is a guy.  I suspect a lot of folks seeing you don't go to the extra effort.

[JeffB]

23 hours ago, Thighbootguy said:

Well done young man, well done. 

I know you keep saying " I don't want to LOOK like a woman, I just want to DRESS like a woman!", but I do think you're starting to LOOK the part. I think it is that the outfits you are assembling fit my stereotyped image what a woman would be wearing, which means you are meeting your goal, but once that "woman image" is triggered in my head I have to work at the extra thinking to realize I'm wrong and the image I'm seeing is a guy.  I suspect a lot of folks seeing you don't go to the extra effort.

Well, that certainly was an interesting theory you presented as it never occurred to me that I could be mistaken for a woman, or that I could present the image of one. Perhaps my insistence on wanting to look my best so I could blend in with surroundings could well trigger that "woman image" you spoke about and that passersby might accept me as female before putting me out of their minds and going about their lives. I'll admit to being intrigued, so I'll continue to live my personal principle as presented in my signature, I love dressing like a woman, whether or not I look like one is a subject open to personal interpretation.

[Thighbootguy]

JeffB, We have a mental image of ourselves that we can't help but project.  This is one of the reasons I have stressed liking what you see in a mirror before you freestyle in public.  With the care you take in developing an outfit, you obviously like the image you are presenting and people pick up on that.  I suspect in developing that image you are not thinking that a guy would look good wearing this combination rather it would look good on a gal and if it looked good for a gal then it would look good when I wear it.

Don't be too surprised if the casual observer reads most of the signals you project with your image as female and fails to pick up on the male signals.  I have been mistaken for a female (only rarely) and been surprised at "Let her go first" and "Yes Mam" comments from others.  I didn't do anything to correct those misinterpretations and later considered them a complement that I might have gotten the look right.

I am not suggesting that your goal should be to pass as a woman but rather you should not be too surprised when you do.

One part of your image that you didn't comment on that is even more important is the "young man" observation.  That is really a mental thing that you can project.  A good healthy dose of the Peter Pan syndrome ("I don't want to grow up") is good for all of us.  Keep yourself young at heart and it will be part of the image you project.

 

[SkirtDude]

10 hours ago, JeffB said:

Well, that certainly was an interesting theory you presented as it never occurred to me that I could be mistaken for a woman, or that I could present the image of one. Perhaps my insistence on wanting to look my best so I could blend in with surroundings could well trigger that "woman image" you spoke about and that passersby might accept me as female before putting me out of their minds and going about their lives. I'll admit to being intrigued, so I'll continue to live my personal principle as presented in my signature, I love dressing like a woman, whether or not I look like one is a subject open to personal interpretation.

I think in the pencil and shorter skirts the look is more masculine,  not sure if its skirt shape or more youthful length  but guys can clearly see you are a man in a skirt (and great shoes),  but I notice your accessories  (necklace etc) are more feminine when you don the "skirts for the older woman". That's just my opinion, and a lot of older women have short natural hair just like yours.

Why not try a skater skirt? They are not all extra short, I have a knee length one which is quite flattering  

Edited August 29, 2016 by heelsrus2000

[JeffB]

TBG: I appreciate your comments which I found highly intriguing. I make a note to study women and what they wear from season to season, then apply what I've seen into the outfits I wear. Just like women, I want to look as good as I can, that's important to me as a fashion freestyler, I guess my work has paid off as I've been accepted for my appearance. The notion of passing as a woman doesn't factor into what I do, but if people take me for female, hey, whatever works for them. As for the "young man" observation, you brought up a good point, and you're right, thinking young and acting young is important, and makes me feel good as well.

heelsrus2000: I must say it hadn't occurred to me that pencil and short skirts might be construed as being masculine, interesting. As for short hairstyles for black women, I Googled that last night and found a goodly number of styles that resemble what I look like. Fascinating!

Jaunt #329, 8/29/2016: The more I venture out in public in skirts and heels, the more I love it, plain and simple. It feels so natural to wear women's clothes and shoes, and lots of fun as well, words can't describe how enjoyable it is to be a fashion freestyler, forging the way for men to break the bonds of gender inequality when it comes to clothing. For yesterday's outing, I had no particular plan in mind, I just wanted to go out and enjoy an outing, which I did in a magenta blouse, a black crinkle skirt, the Payless "Tawny" wedge slides and a black handbag. As a rule, I almost never wear the same shoes on back to back outings, but I've come to like the Tawny slides which are stylish, easy to walk in and look good on me. Regarding the skirt, even though temps reached into the low 90's, I didn't at all feel uncomfortable in the shin length number I sported, even though it's lined, I was perfectly comfortable in it. Lastly, the blouse which I thought was cute and feminine and tailor made for summertime wear as I no longer want to wear anything on my outings that look even remotely masculine.

So, I headed to my usual haunt downtown, Rittenhouse Square Park. Now, since it was a weekday, the park wasn't quite so crowded as it is on weekends, even with kids still out on summer vacation, finding a bench as easy, given the lack of crowds, so I sat with the paper which I read while people came and went, ignoring me all the while, after I finished my paper, I just relaxed and enjoyed a nice little breeze the blew through. An hour later, I wandered down the street to McDonalds for lunch, I did get a stare or two, but nothing more, then I returned to my car and, on a whim, motored over into South Jersey and a multiplex at Moorestown Mall where I watched Don't Breathe which was a creepy and chilling flick that had me on the edge of my seat at times. Well worth watching. After the movie, I ventured out into the mall which wasn't too terribly crowded at 3:30 in the afternoon, I went to Sears where I bought four more blouses like the one I wore in the pictures below, then wandered back into the mall, looking about the place and pausing to sit on a chair and check my email on my smartphone for some ten to fifteen minutes before I returned to my car and headed home before the traffic got too crazy.

You see, the thing about my outings is that I seek to be simply another person out and about, doing this and doing that. I don't look to be noticed or draw attention to myself (and I've been doing a good job of that), just like everybody else, which is why I strive to dress appropriately for the surroundings I happen to be in, and for me, it's both fun and empowering. More to come....

[SkirtDude]

wow.. quite a change... you do you, hun!

I guess we'll be seeing a more female persona from you soon as well. 

All the best - I will watch from the sidelines in puzzlement anticipation of what's worn next  

Edited August 30, 2016 by heelsrus2000

[Thighbootguy]

Great look JeffB.  The longer skirt suits you well and the necklace completes the image.  I fight a constant battle between dressing in age appropriate outfits (longer skirt, lower heels) and my "way too young" mental image (mini skirts and thigh boots).  I do suffer with the Peter Pan syndrome.  I am comfortable with either presentation but the age appropriate one is generally more accepted.

The short hair really does work well with your image and shorter might even work better.

[JeffB]

16 hours ago, heelsrus2000 said:

wow.. quite a change... you do you, hun!

I guess we'll be seeing a more female persona from you soon as well. 

All the best - I will watch from the sidelines in puzzlement anticipation of what's worn next  

A more female persona? Well, I don't know about that, still, for me, it's all about dressing like a woman.

14 minutes ago, Thighbootguy said:

Great look JeffB.  The longer skirt suits you well and the necklace completes the image.  I fight a constant battle between dressing in age appropriate outfits (longer skirt, lower heels) and my "way too young" mental image (mini skirts and thigh boots).  I do suffer with the Peter Pan syndrome.  I am comfortable with either presentation but the age appropriate one is generally more accepted.

The short hair really does work well with your image and shorter might even work better.

I find that longer skirts like what I've worn the last couple of outings lends me an elegant air as I enjoy dressing my age, and I like that particular look. But, I won't give up on shorter skirts as I do like them. As for shorter hair, perhaps I'll get a haircut before the week closes.

[kikepa]

22 hours ago, JeffB said:

A more female persona? Well, I don't know about that, still, for me, it's all about dressing like a woman.

I find that longer skirts like what I've worn the last couple of outings lends me an elegant air as I enjoy dressing my age, and I like that particular look. But, I won't give up on shorter skirts as I do like them. As for shorter hair, perhaps I'll get a haircut before the week closes.

My eight-year rut is largely very non-descript heels in public or the occasional mannerrock (German for "men's skirt" usually worn with boots).

At home, though, I'm usually in a sarong and loose, long shirt and sandals.  

Society still isn't ready to both see me and employ me.

[JeffB]

Jaunt #330, 8/31/2016: After two straight outings where I dressed up, relatively speaking, I went casual on a sunny and humid day, sporting an apricot colored tank top, my Old Navy 20 inch dark denim pencil skirt, the Payless "Noble" flat sandals in black and a matching handbag. I'm sure I've said this before, but there was a certain....something about wearing flat sandals that was, in their own way, more fun to me than wearing high heels, just another part of my ongoing evolution as a freestyler as I enjoy wearing ALL styles of women's shoes. Oh, yeah, that outing marked the 200th time I've worn Payless shoes in this thread. I headed out to Springfield and Acme to buy a couple of odds and ends (nothing perishable, given the heat) and to buy the Powerball Lottery ticket, then it was off to my home away from home, Best Buy, since I hadn't been there for a couple of outings, it was good to visit there to wander around and gaze at all the electronic gadgets both big and small for well over half an hour before going to the register with a Blu-Ray copy of Batman v. Superman. While I didn't think it was all that great in the multiplex, perhaps that opinion will change after viewing it at home.

After swinging by Arby's for lunch, I decided to go downtown and my regular haunt, Rittenhouse Square Park to read the paper and soak in the ambiance about the park that I so enjoy. I won't bore you, dear reader with reports on reactions from passersby regarding my attire, because, as usual, there weren't any, however, there had been one person who caught my attention, and in a big way. I had just finished my paper and put it down when, out of the corner of my eye, a tall, thin, older gentleman in glasses with long, thick, Snow White hair done up in a bun, moustache and beard to match quickly strolled by. What's the big deal you ask? Well, that gentleman was attired in a long sleeved, gray minidress, white anklets, brown, three inch heeled clogs and an oversized handbag. Yes, folks, I had seen my very first fashion freestyler. Awesome, eh? Needless to say, I was floored because I had never experienced this before, the gentleman, whom I'm sure never saw me in passing, looked decent in his outfit (though one could argue against wearing anklets with clogs) and seemed to carry himself with the same sort of air that I did. I'll admit to having been rather impressed with his overall appearance, and his boldness.

I thought about calling out to the gentleman, but he looked to have been in a hurry and was out of sight in a minute, leaving the park and walking across the street. As near as I could tell, he garnered no more odd or strange looks than I do, and I admired him for a successful appearance. Still, I wish he had seen me, I'm sure that might have made for a rather interesting interaction. So, in the span of a minute or so, I got positive confirmation that I wasn't the only man in the greater downtown Philadelphia area who wore women's clothes and shoes. Plenty darn cool if I do say so myself. More to come....

[Thighbootguy]

Cool outfit in both meanings of the word.  The haircut looks good but I'm not too taken with the tank top.  To my eye either short sleeves, a light weight blazer, or more sun on your upper arms would improve the look.