The Jaunts of JeffB!

[maninpumps]

I like the T strap wedges . Looking good !

[Lime15]

You look great as usual!

[bluejay]

JeffB,

 

Those were two nice looking ensembles, you wore this past weekend. Thanks for the post and the pics too!

 

Happy Heeling,

bluejay

[JeffB]

I like the T strap wedges . Looking good !

 

 

You look great as usual!

 

 

JeffB,

 

Those were two nice looking ensembles, you wore this past weekend. Thanks for the post and the pics too!

 

Happy Heeling,

bluejay

 

Thanks for the kinds words, everybody! I enjoy getting compliments, especially from my peers here at HHP!

[JeffB]

Jaunt #225, 5/31/2014:

With plenty of sunshine and warm temps, I closed out May with a jaunt, going out in a royal blue campshirt, my 17 Old Navy olive cargo skirt, the Payless "Salliana" platform wedge sandals and my black faux croc handbag. Because of how hot it was yesterday, I felt perfectly cool and comfortable in my short skirt, and that was a delightful feeling. Meanwhile, I believe I experienced another paradigm shift, for years and years, I only wore 'closed' shoes like pumps and loafers, the concept of wearing sandals was as alien to me then as wearing pants or jeans on my outings are to me now. And yet, I've really come to enjoy wearing sandals, especially my Payless platform wedges which continue to amaze me with their deceptive level of comfort and ease of wear, not to mention how much fun they are to wear to boot. With warm weather here, I suspect I'll be spending a goodly amount of time in my sandals.

 

But I digress. Driving into town, it took a good half hour to find a parking spot close to my friendly neighborhood comic shop, well, if you call nearly two blocks away from said shop 'close', but I didn't mind since I got to enjoy a good walk, and to be seen. Waiting at a corner near a bistro with diners outside, a trio of young women attracted my attention, smiled at me and said they liked my shoes and that they looked, in their words, "cool on me". I smiled back and thanked them before continuing on my way. As always, it's great to get compliments, though it was kinda funny they didn't say anything about the skirt, perhaps they didn't find that to have been a big deal while the shoes were to them. After my visit to the comic shop and returning to my car, I drove over into South Jersey and to the Moorestown Mall area, lunch today was at Chick-Fil-A, I hopped out and headed in, other than a couple of long looks from a few kids, no one paid me much mind as I ate, even though the restaurant was fairly full. I've found it commonplace that kids take a somewhat active interest in my eclectic appearance while adults mainly ignore me and give me my space.

 

From there, it was off to Barnes & Noble where I enjoyed the quiet and mellow atmosphere where I read a few sci-fi and movie magazine for well over half and hour before going to the checkout line with an anime magazine. My last stop of the day was to the nearby Sears for some clothes shopping, there's a certain...something about strolling the aisles in the women's clothing department that I find very relaxing and enjoyable, I finally bought a couple of tank tops and a nice two piece top and long skirt outfit in navy that I'll show off to everyone soon. More fun to come....

Jaunt #226, 6/1/2014:

With the weather on Sunday being just as sunny and warm and delightful as Saturday, I headed out on an outing in the outfit I bought at Sears and mentioned in the post above, that being a navy, sleeveless crinkle styled top and a matching 36 inch long peasant skirt, and since Memorial Day had come and gone, I paired the outfit with the Payless "Margaret" espadrille wedges in white and a matching white handbag. I thought this was a good looking outfit that felt good to wear. And because the outfit was light and airy, I was perfectly comfortable and at ease.

 

My first of three stops that day was to the main branch of the city's Post Office to buy a money order to renew my newspaper subscription. I arrived around 12:15, after it's noontime opening, so there was a bit of a line which I had to stand in for a solid ten to twelve minutes before getting to the counter to buy my money order which I filled out, stuffed in the envelope and dropped off. The whole time, no one game the time of day, no odd looks, no titters, giggles, pointed fingers or anything. Leaving the Post Office, I drove over into South Jersey and to the Moorestown Mall area where I had lunch at Boston Market, a tasty Boston Carver meat loaf sandwich with mashed potatoes and a bottle of water, a darn good lunch to say the least, and, just like at the Post Office, no one bothered me. From there, my last stop of the day, and the longest was at the nearby Barnes & Noble where I relaxed for little over an hour with a bottle of lemonade and the Sunday paper in a nice and quiet environment where no one paid any attention to what I wore.

 

Once again, I felt that by being tastefully dressed for my surroundings, despite being garbed head to toe in women's clothing, I was able to blend in and be accepted for who I was: a guy in a skirt and heels, nothing more, nothing less.

[Mr. X]

Always good to read about you out doing your thing Jeff.  Keep it up!

[JeffB]

Many thanks, Mr. X! I appreciate folks like yourself who enjoy reading my exploits!

[bluejay]

Nice looking ensembles, JeffB.

 

I'm glad to see you wearing your white wedge heels. I've worn my new Nine West , white, peep toe pumps out last weekend too. I got several compliments paired up with my new hot pink , blazer. As one young woman put it, "I looked delicious", to her.

 

Happy Heeling

bluejay

[JeffB]

Nice looking ensembles, JeffB. I'm glad to see you wearing your white wedge heels. I've worn my new Nine West , white, peep toe pumps out last weekend too. I got several compliments paired up with my new hot pink , blazer. As one young woman put it, "I looked delicious", to her. Happy Heeling bluejay

Thanks! Yes, the Margaret espadrilles are seriously great shoes, either in black or white, and I just love wearing them. I recently bought a white denim skirt at Old Navy that I'll take for a spin with the white wedges real soon.

[JeffB]

Well, it looks like I've had yet another paradigm shift in my freestyling philosophy. From day one as a heel wearer, I've preferred pumps, a.k.a. "closed" shoes because they were what I liked most and was what I was used to. The concept of wearing sandals (a.k.a. "open" shoes) was completely alien to me and I avoided them like the plague because I just didn't like the look of them and I thought they'd look awful on my feet. Then, last year, I experimented with a shoe that combined not one, not two, but THREE footwear elements that I originally had little love for: the Payless "Molly" which was A) a sandal, B ) had a platform, and C) was a wedge. The first time I wore those shoes, I was instantly amazed and fell in love because of how deceptively comfortable they were and how ridiculously easy they were to stand and walk in, despite their five inch heels. Suddenly I found sandals to be cool and fun shoes, and platform wedge sandals tripled the fun, so much so that I now have five pairs, and I enjoy the heck out of them as they look great on me, especially when I pair them with skirts, both long and short. The last time I've worn pumps was I believe, early May, but with spring here and summer right around the corner, I've gone almost exclusively with my sandals, the perfect shoe for the current season, something I NEVER would've considered a year or two ago.

[SF]

Jeff, How you??  We are almost exactly the opposite when it comes to shoe styles.  I am a sandal fan, have been since I was a kid.  Flats, heels, wedgies, strappy, thongs, all are fine with me as long as it is a sandal style.  I guess I have 40+ pairs of sandals, about half of those are heels.  I just like the look and feel of sandals.  Weather does play a part though, out here on the west coast the temps are a bit milder and I can actually wear sandals most all year long.  

I did make the jump last January and actually bought a pair of Aerosoles pumps that I fully enjoy wearing, especially on cooler days.  I had wondered about pumps and after being encouraged by some folks here (you know who you are) to try a pair, I did - and found them enjoyable as well.  

Like you I also enjoy wearing my heels, flats, sandals and pumps in public…  It's fun…  take care, sf

[JeffB]

Hey there, SF! Thanks for writing! As a late devotee to sandals, I can fully understand your appreciation of these shoes since they've been fairly much all I've worn of late, and I like them too! I'm glad you've come to enjoy pumps! Cool!

[ilikekicks]

JeffB : I remember when I first joined this site and you were contemplating wedges. Now, your rocking just about everything, a full plate of style. Wedges, Pumps, Sandals.. Your the ' full package ' so to say in those regards.

 

I wish I could sport the variety of fashion you do but im not as rangeful in what I feel comfortable in.

 

-ILK

[JeffB]

JeffB : I remember when I first joined this site and you were contemplating wedges. Now, your rocking just about everything, a full plate of style. Wedges, Pumps, Sandals.. Your the ' full package ' so to say in those regards.

 

I wish I could sport the variety of fashion you do but im not as rangeful in what I feel comfortable in.

 

-ILK

 

Don't forget boots, flats and loafers! When it comes to footwear, I'm all over the map! Variety is the spice of life! 

[JeffB]

Jaunt #227, 6/14/2014:

After a cold front blew through early Friday evening with some spotty thunderstorms, things cooled down considerably on Saturday as the weather was sunny, mild and bright, so I was off on a short jaunt before that day's World Cup action, wearing a red campshirt with a black denim pencil skirt, the Payless "Margaret" espadrille wedges and a black handbag. I must say that there's a certain....something about wearing a snug black skirt that's truly exciting to me, and the Margaret wedges are truly fun shoes I've quickly come to love wearing. Driving into town, I stopped near a branch of my bank to tap an ATM, after crossing the street, I passed an Asian couple in their 40's, and they both looked at me in almost comedic confusion. From there, I returned to my car and drove to my local comic book shop, parked half a block away and enjoyed a little walk to the shop, then walked a block up the street to a local convienence store for a newspaper.

 

After returning to my car, I headed west into Springfield and to Best Buy where I spent well over half an hour gazing and gawking, no one paid me much, if any attention the whole time I was in the store which was nothing new to me. From there, I was off down the road to Subway for lunch, it was around 12:30 or so when I arrived, when I walked in, there was a classic nuclear family (mother, father, two young kids) ahead of me, and the kids stared me up and down in, well, childlike wonder right on up to the time they left the shop while mom and dad chose to ignore me. I found that rather humorous, even moreso than my brief encounter with that Asian couple downtown. It is indeed interesting the reactions I sometimes get from what I choose to wear, as is often the case, the majority of people, too wrapped up in their own lives and affairs, don't bother to pay any attention to a middle aged guy in a skirt and heels, but for those who do, the reactions are noteworthy. Perhaps I'm an anomaly to them, who can say for sure. Anyhoo, while brief, my outing was enjoyable, and that's the important thing.

[Mr. X]

Way to go Jeff!  Way to show people that some men can look just as good in a skirt as women do!

[JeffB]

Way to go Jeff!  Way to show people that some men can look just as good in a skirt as women do!

 

Thanks for the kind words, Mr. X. Ever since I fully devoted myself to being a fashion freestyler, my objective was to look my very best in clothes worn by the opposite sex. I want to put the idea in people's heads that a guy can look just as normal in a skirt as any woman, and I think I'm getting closer to that goal all the time.

[maninpumps]

The wedges look great on you ! Jeff you are an inspiration to us all. 

[SleekHeels]

Thanks for the kind words, Mr. X. Ever since I fully devoted myself to being a fashion freestyler, my objective was to look my very best in clothes worn by the opposite sex. I want to put the idea in people's heads that a guy can look just as normal in a skirt as any woman, and I think I'm getting closer to that goal all the time.

 

I can relate to that Jeff. We're still a tiny minority and many people find it easier to react in a very conditioned way, but I think we do press people's "challenge preconceptions" button - whether that button is wired up to anything or not depends on the person, but I think more people than we realise do respond in an intelligent, open-minded way even if they don't show it.

[JeffB]

The wedges look great on you ! Jeff you are an inspiration to us all. 

 

Many thanks, my friend. I simply do the very best I can. I've been crazy about wedges of late and they've been all I've worn on my recent outings because I like them so much. I never would've said that a year or two ago.

 

I can relate to that Jeff. We're still a tiny minority and many people find it easier to react in a very conditioned way, but I think we do press people's "challenge preconceptions" button - whether that button is wired up to anything or not depends on the person, but I think more people than we realise do respond in an intelligent, open-minded way even if they don't show it.

 

I suppose that "conditioned way" probably is to simply ignore us. As I've said many times before, people are too wrapped up in their own lives and affairs to pay much attention to us, which is cool with me. When it comes to challenging perceptions, the only way to accomplish that goal is to simply go out and do it. I'm of the belief that the more freestylers are seen, the less uncommon we become, especially if we present a tasteful, stylish and appropriate appearance to the world at large.

[SF]

Mr. JeffB, A question.  How do you handle the situation when, during your jaunts, you run across folks that you know, work with or otherwise are familiar with?  

Does the moment get awkward?  

I wear heels a lot as a guy and a few times I have met folks I know in public.  Most of the time they say nothing - probably don't even notice - and other times they may mention my shoes, and ask why I am wearing high heels.  My usual response is that I saw the shoes, liked the look and bought them to wear.  That usually ends the shoe discussion.  No one has ever been judgmental or negative.  I am sure that most then hit the "rumor mill" to tell whoever that they saw me wearing high heels!  ha ha  

Since you also wear gals clothing, I would imagine that just adds another dimension to the subject.  Just wondering what you do when the situation arises…??

Thanks, sf  

[JeffB]

SF: Well, I've been fortunate in that I've yet to run into anyone I know, either from from work or from my block while on an outing, so I'd have no way of knowing just how to react. Guess I've been lucky.

[mlroseplant]

SF: Well, I've been fortunate in that I've yet to run into anyone I know, either from from work or from my block while on an outing, so I'd have no way of knowing just how to react. Guess I've been lucky.

Jeff, your comment really surprised me. I have been inspired by your confidence and your style. I never realized that your neighbors and colleagues are apparently unaware of your true awesomeness. Yeah, ok, I'm laying it on kind of thick, but I hope you understand the sentiment. For the first time since I've been reading of your jaunts, I feel like I can perhaps give some useful advice. The advice is this: Just smile, and be yourself. I posted this elsewhere, but recently I went on an evening walk wearing much more feminine shoes than I normally wear, and I ran into EVERYBODY. And you know what? I'm glad that I did. It's good to connect with your neighbors and colleagues. I think that if people like you anyhow, they aren't going to stop liking you because of your unconventional dress. Smile! Be yourself! That's all I got.

[JeffB]

miro: Well, I simply do the very best I can, so far, things have worked out pretty good. And yes, smiling is definitely a good thing indeed!

 

Jaunt #228, 6/21/2014:

Not that I needed an excuse or anything like that, but I celebrated the first day of summer with a new jaunt, going out in a blue embroidered tank top, a 40 inch black maxiskirt, the Payless "Thatcher" platform wedge sandals and my black faux croc handbag. Not that I'm counting or anything like that (okay, I am), but this made my thirteenth straight outing in wedges, including the "Cori" one inch flats, the "Margaret" peep toe espadrilles and my way cool platform sandals, I haven't worn traditional heels since early April as my love for wedges has intensified, something I never envisioned a couple of years ago, they've simply been the only shoes I've wanted to wear of late. And while I like showing off my legs in a short skirt, there's a certain....something about wearing a long, flowing, filmy maxi that puts me in touch with my femininity, and that's a good feeling to me.

 

But I digress. My first stop was to a local branch of my bank in the University City area for some cash. After parking half a block from the bank, I hopped out, paid the meter and strolled to the bank, eliciting a couple of turned heads here and there, in the bank, a young child with her mother looked me up and down while I used the ATM but both said nothing while I was there. My next stop was to my favorite comic shop, after parking a few doors down from the shop, I got out and went in, spending a good twenty minutes or so there, no big deal as the folks who run the place are long used to me and the clothes I wear. From there, I walked a block up the street to a nearby convenience store to buy a newspaper, I got a few more stares, but nothing more than that, I simply maintain my usual calm and cool demeanor, like what I had on was no big deal, but I enjoyed how the long skirt swished about my ankles and the fun that came from wearing my sandals which are cooler shoes than I realized. At the store, I chatted briefly with the twentysomething Asian lady behind the counter about the weather, then complimented me on the necklace I wore. I smiled and thanked her.

 

From there, it was off to South Jersey and to the Moorestown Mall area where I ate at Chick-Fil-A. I got my fair share of stares and turned heads here, but I paid that no mind as I enjoyed my lunch. Then I went to Barnes & Noble for some quiet time reading Sci-Fi magazines with a bottle of lemonade for nearly an hour before leaving with a manga title, but that, as usual was a pleasant experience as I was left alone, no stares, no turned heads, nothing. My last stop of the day was at Home Depot as I needed a window fan for the small bedroom at the house which I use as my home office, I got a few stares here, no big deal as it didn't take long to find what I needed, paid for it then left for home. All in all, another enjoyable outing, I couldn't help but notice how I got more stares wearing a long skirt than I do in a short one, most unusual to say the least, but hey, that's how things sometimes go when you're a freestyler.

[maninpumps]

Nice look with the skirt. I have always liked long skirts.

[SleekHeels]

mI couldn't help but notice how I got more stares wearing a long skirt than I do in a short one, most unusual to say the least, but hey, that's how things sometimes go when you're a freestyler.

 

The colour combination is simple and effective, I really like it, and the style is great too.

 

As for the stares, don't you find that they are subtly different depending on what you're wearing? I know I sometimes over-dress a little (skirt a little too short and heels a little too high, but hey, it's fun to do that sometimes) and the stares can be a little mocking/disapproving, or people just assume the clothes/shoes are just a sex thing. But a more modest outfit, such as the long skirt and wedges you wore, tends to eliminate that perceived fetish element, and people still stare but in a different way, as if they can't quite get their heads around the fact that you might actually enjoy dressing that way simply for the pleasure and style of it. I think that challenges peoples prejudices more, they can't quite dismiss their confusion by laughing it off. Also, not all stares are bad, sometimes people stare in a way that says they'd like to say something nice but they've been caught off-guard. Do you feel that variety of stares in your experience too?

[bluejay]

Well Done JeffB. I like your look very much. I'm glad you enjoyed yourself out and about on Saturday.

 

Like you , I'm wearing my share of wedge heel sandals too. I been wearing, my UGGS, "Tawnie" wedge heel, slide sandals with 5" heels and 1" platform. I love wearing them. They are easy to walk in and I have them in 5 colors. Most women that compliment me on them can hardly believe they are UGGS. I have to take one off to show them the UGGS tag.

 

Tonight, I wore my white, Covington (Sears) "Rivera" wedge heel slides, with emerald green, jean capris, white polo shirt and carried my white, Style & Co (Kohl's), white cross body bag. I got a couple compliments on my appearance from, the ladies. Love those compliments!

 

BTW, thanks for the post and pics too.

 

Happy Heeling,

bluejay

[JeffB]

maninpumps: Thanks for the kind words. Much appreciated! I've found that wearing long, breezy skirts to be great fun. I plan to do that more.

 

SleekHeels: I've found your comments most interesting. Yes, you're right about how stares can be interpreted in many different ways. I've gotten stares that mostly conveyed confusion or puzzlement, especially young kids, like they, and adults are internally struggling to comprehend what they've seen. However, it's exceedingly rare these days for me to get stares of amusement, like I'm an object of humor or derision, I think that when people see me, they more or less accept what I'm wearing, then return to their own lives and affairs. I'm like Halley's Comet to most, something they see only once, then never again. Of course, dressing tastefully and appropriately for the surroundings I happen to be in goes a long ways to towards eliminating the amusement/derision component, because I don't dress outrageously, people have a hard time finding anything to laugh or make fun about. I take great pride and go to great lengths in presenting the sort of positive image that says to the world that men CAN wear women's clothes AS MEN and not look comical or freakish.

 

bluejay: I've said this already, but I'm pretty much crazy about wedges. Every time I've put together an outfit for an outing, I've instinctively reached for wedges first for footwear, and my platform sandals have been at the top of the list of late because of the warmer weather, and that they're such crazy fun shoes to wear! Meanwhile, your latest outfit sounds plenty cool, no wonder you got compliments!

[Steve63130]

The colour combination is simple and effective, I really like it, and the style is great too.

 

As for the stares, don't you find that they are subtly different depending on what you're wearing? I know I sometimes over-dress a little (skirt a little too short and heels a little too high, but hey, it's fun to do that sometimes) and the stares can be a little mocking/disapproving, or people just assume the clothes/shoes are just a sex thing. But a more modest outfit, such as the long skirt and wedges you wore, tends to eliminate that perceived fetish element, and people still stare but in a different way, as if they can't quite get their heads around the fact that you might actually enjoy dressing that way simply for the pleasure and style of it. I think that challenges peoples prejudices more, they can't quite dismiss their confusion by laughing it off. Also, not all stares are bad, sometimes people stare in a way that says they'd like to say something nice but they've been caught off-guard. Do you feel that variety of stares in your experience too?

Well stated! Stares don't equate with disapproval. We are brought up in a culture that teaches us that there are two and only two genders and there is no spectrum in between (although that's finally starting to change). Men are to wear men's clothing and women are to wear women's clothing. So in our minds there are these two pigeonholes, and in an effort to make sense of what we observe, when we see a guy in men's clothing, that's the men's pigeonhole. When we see a gal in women's clothing, that's the women's pigeonhole. So what happens when we see a woman in men's clothing? Well, we've been conditioned to accept that, so that's really a third pigeonhole. But a man in women's clothing (tastefully done, let's assume)? There is no pigeonhole for that. No recollection of having seen that before. If the clothes looked goofy, with badly matched colors or a silly style (like a tutu for instance) or fake boobs, then the reaction might be laughter. But if the guy is well dressed, like Bluejay, JeffB and you, Sleekheels, then the reaction isn't laughter; it's trying to verify that the viewer is really seeing what he is seeing, and perhaps trying to understand why, since it's so rare. Most people really don't understand cross-dressing or sexual orientation, and often confuse the two, falsely assuming a guy in heels is gay. It's up to us to educate the unwashed masses by good example, and you guys are exemplary. My compliments!

 

Steve

[Shafted]

Well stated! Stares don't equate with disapproval. We are brought up in a culture that teaches us that there are two and only two genders and there is no spectrum in between (although that's finally starting to change). Men are to wear men's clothing and women are to wear women's clothing. So in our minds there are these two pigeonholes, and in an effort to make sense of what we observe, when we see a guy in men's clothing, that's the men's pigeonhole. When we see a gal in women's clothing, that's the women's pigeonhole. So what happens when we see a woman in men's clothing? Well, we've been conditioned to accept that, so that's really a third pigeonhole. But a man in women's clothing (tastefully done, let's assume)? There is no pigeonhole for that. No recollection of having seen that before. If the clothes looked goofy, with badly matched colors or a silly style (like a tutu for instance) or fake boobs, then the reaction might be laughter. But if the guy is well dressed, like Bluejay, JeffB and you, Sleekheels, then the reaction isn't laughter; it's trying to verify that the viewer is really seeing what he is seeing, and perhaps trying to understand why, since it's so rare. Most people really don't understand cross-dressing or sexual orientation, and often confuse the two, falsely assuming a guy in heels is gay. It's up to us to educate the unwashed masses by good example, and you guys are exemplary. My compliments!

 

Steve

I'm speechless, but ditto, Steve.

 

A most interesting tangent to your thread Jeff.