JeffB

Jaunt #337, 10/17/2016: Last Monday, I was wearing a jacket, tights and knee boots as the weather was crisp and chilly. A week later, temps were in the low 80's as it felt more like late summer than early fall. Amazing! Anyhoo, that motivated me to run a couple of errands after work as a brief jaunt, attired in a brown embroidered tank top, an 18 inch Old Navy khaki skirt, the Payless "Margarita" low wedge slides in natural and a matching handbag. Nothing fancy or flashy, just a purely casual outfit for a little running around.

I headed west into Springfield, stopping at Acme supermarket to stock up on flavored sparkling water which I've come to enjoy of late, it was about 4:30 in the afternoon and the market was plenty full, yet, as usual, I wandered the aisles with nary a look, save from a middle aged lady ahead of me in line who said she liked my tank, and I thanked her for the compliment. After leaving the market, I headed down the road to my home away from home, Best Buy where I indulged in something I've wanted for awhile, Bluetooth earbuds for my iPhone so I don't have to deal with annoying wires with wired earbuds, and they're plenty cool, I wish I had bought a pair long ago.

Even though it was a short outing, just under an hour and a half, anytime I can go out in a skirt and heels, be they low or high, it's a good time, and it always feels great to wear women's clothes in public. More to come....

Jaunt #336, 10/15/2016: Ahhh, nothing like a sunny and crisp Saturday for an outing, and with temps around the mid to upper 60's, the weather was perfect for wearing my denim jacket over a pink tank top, the blue denim button down skirt, the Payless "Cori" wedge flats and a black handbag. I hadn't worn the Cori shoes in awhile, but they were comfy and tailor made for the purely casual outfit I wore, as for the tank, I rather enjoyed the low cut profile, I'd even go so far as to say the neckline gives me the illusion of displaying cleavage, and I found that to be lots of fun. Oh, yeah, I have no problem whatsoever with wearing pink in public, heck, I like it a lot.

My first stop was downtown where I parked a block away from my friendly neighborhood comic book shop where I headed first and yakked with one of the co-workers about the upcoming Eagles-Redskins game, then I strolled five blocks down the street, crowded as always on Saturday to One Liberty Place for lunch, of course, no one gave me so much as a glance or a sideways look, and that's fine by me, it means I've succeeded in putting together the sort of outfit that enables me to blend in with my surroundings, something I've been pretty much obsessed about ever since I made the bold step to wear women's clothes and shoes on my outings, a passion I take very seriously. Reaching the building, I strolled right in and went up to the second floor where the food court is and had a chicken salad sandwich and a bottle of water from Chick-Fil-A. There wasn't as much of a crowd as there would be on a weekday when it's packed to the gills, but that was cool. After lunch, I headed back to the car, along the way, I passed by half a dozen women wearing pink tops and workout gear, one of them said to me, "Thanks for wearing pink! It helps a lot!" For those who may not know it, October is Breast Cancer Awareness Month, and pink is the color for this special month.

Back in the car, I drove over the Ben Franklin Bridge to South Jersey and headed to Sears at the Moorestown Mall where I did a little shopping, and yes, I bought some new skirts, a guy can never have too many skirts, and these three knee length knit A-lines I bought in black, gray and plaid looked good. You'll see them on future outings. I then walked into the mall and wandered around, passing people left and right with nary an old look, stare or double take, and that felt plenty good, being able to blend in, and that's plenty enjoyable, I even sat in a chair and fiddled on my phone for some fifteen minutes. No big deal at all because I acted like I belonged there, and I did, nothing more, nothing less. I continue being living proof that public fashion freestyling can be done, and done well. More to come....

Henri1942 & heelsrus2000: Thanks for the kind words.

11 hours ago, CPB said:

Very smart outfit. Well put together as usual .

Thanks for the kind words!

Jaunt #335, 10/10/2016: The combination of the threadbare remnants of Hurricane Matthew that blew through as afternoon rain, followed by a cold front that came in overnight, leading to morning rain resulted in a sunny and chilly Columbus Day, and since I had the day off, I was eager to go on an outing, garbed in my black faux leather jacket over a blue t-shirt, the gray denim 16 inch miniskirt with the distressed hem, black tights, the Walking Cradles "Elites" riding boots and a black handbag. Even though it was rather chilly, despite the sunshine, I was quite comfortable, especially with the tights I had on, and it sure felt good to wear the riding boots again which looked sharp paired with the short skirt. My first stop was into Springfield and Best Buy where I haven't visited for a few weeks and I spent well over half and hour there before leaving with a Blu-Ray copy of Attack On Titan, a live action film version of the popular Japanese manga and anime.

My second stop was downtown, yep, my regular center city haunt of Rittenhouse Square where I parked around 12:30 p.m., the downtown area was plenty crowded since it was a holiday for most, so the streets were plenty packed as I strolled down to One Liberty Place and it's second floor food court for lunch. On the way there, I was at a corner when a youngish woman in glasses smiled at me and said she liked my boots, I thanked her and said I bought them at Maryland Square, she nodded and said she'd looked up the website. The court was fairly full too, but, like on the street, no one paid me any attention as I bought a corned beef special with a bottle of water from Bain's Deli, then I retreated to a table to eat, surrounded by all sorts of people where I ate in complete peace. After I finished eating, I went down to the ground floor rotunda, took a seat and read my newspaper for about half an hour while people came and went, ignoring me the whole time while I was in plain view of everyone in sight. Once I finished reading, I packed up, left and strolled back up the street to where my car was, surrounded by crowds of people who didn't give me so much as the time of day, when I was block from where I parked, a young black man coming towards me said in passing, "I like your hook-up", I grinned and thanked him.

I know I've said this more than a few times in this thread, but it never fails to amaze me just how easy it is to do what I do, to come and go in women's clothes and footwear without a lick of trouble or attracting any attention from passersby, and it was a boatload of fun, something that never gets old for me. More to come....

Cool boots, CAT! They look great on you!

11 hours ago, RonC said:

Jeff - I hope you didn't take my comments in a negative way, as that certainly wasn't how they were meant.  Just trying to indicate that my enjoyment comes from a different angle.  I appreciate what you do - personally, I just don;t see myself walking around in a dress or skirt in my otherwise male appearance.  But then I am not trim like you, nor am I as young.  The whole idea is to enjoy what we do here - be it shoes only or full outfits.  So have fun with it! 

Negative way? Nope, not at all. Not everyone here can do what I do, we're all individuals with our own goals and objectives and dreams. As long as you're content with what you enjoy, that's the important thing.

8 hours ago, mlroseplant said:

I had never really thought about this before in quite this way, but yeah, that's me too. In fact, I hardly even notice your shoes these days, Jeff, and perhaps that is your goal. 

I agree with Ron. There is something about the feel of wearing a substantially steep heel that I find attractive and comforting. If I could only wear shoes such as your new booties (which are very sharp, by the way), I probably wouldn't even bother with wearing women's style shoes at all. 

Well, I like to think it is as my goal is the complete package, the overall appearance, not just one article of clothing or footwear. I put a lot of time and attention to my appearance, in looking my best, and I'm glad my hard work has paid off.

5 hours ago, Thighbootguy said:

Feeling somewhere between , , , and .

Kidding aside, that is quite a complement on how well JeffB's outfits are put together.

Thanks for the kind words, TBG! Much appreciated.

CAT: Thanks for your kind words!

RonC: I found your comments most interesting. Yes, I am all about the complete look these days from head to toe, I feel perfectly content wearing anything from flat sandals to five inch heeled thigh boots. To me, I more than likely would've lost interest in high heels if they were all I wore, evolving to wearing clothes and shoes has greatened my appreciation, and enjoyment for women's wear. And I wouldn't have it any other way.

Thanks for the kind words, everybody! I kinda thought the booties would attract attention for the gang here, and I certainly enjoyed wearing them the other day. And I look forward to wearing the booties again soon!

Bought these cute booties, the "Martinez" from Payless on Saturday. They sport 2 1/2 stacked heels which sound delightfully loud on pavement as I broke them in on an outing yesterday. They also come in tan which I might buy next.

Looks lovely. As for me, at six foot two, most gowns would barely reach to my ankles, and that's before adding heels which would make things look more awkward. And yeah, I don't have a figure for one either.

Jaunt #334, 10/2/2016: I'll be the first person to tell you I'm no fashionista, but I do make a note to study what women wear, then do as best I can to emulate what I see, and that was the case with today's outfit. After a cloudy, rainy and cool Saturday, today was a repeat except for the rain, and with some time to kill before the day's NFL action, I headed out in my trusty denim jacket over a red t-shirt, a black denim pencil skirt, a black handbag and my newest footwear acquisition from Payless, the "Martinez" black faux suede booties. Now, I've seen lots of women wearing booties now that fall is here, so I decided to give them a try and bought a pair of my own on Saturday, I found them to have been cute and comfortable while the 2 1/2 inch stacked heels were delightfully loud on the pavement. I can't wait for later on in the season to pair the booties with black tights which would make for a nice look. Meanwhile, today's outing was my 250th in a skirt, quite an accomplishment, given the humble origins of this thread some eight years ago this month, and wearing skirts on my adventures has become very important to me as a freestyler.

My first stop was to Springfield and Acme supermarket to buy a couple of odds and ends, the only look I got from from a young child who was leaving the store with his mother while I was leaving, no big deal, that sort of thing happens all the time. After leaving Acme with my parcels (ten bottles of sparkling water), I headed back into town and center city to fiddle around for awhile, after parking the car, I took a leisurely walk to Barnes & Noble to look around, leaving with a new anime magazine, after leaving, I walked three blocks down the street to One Liberty Square (a skyscraper office building) and it's second floor food court for lunch, enjoying a corned beef special at Bain's Deli, unlike weekdays or even Saturdays, there wasn't too much of a crowd, but there were enough people who saw me and, as usual, no one paid me any attention which is pretty much par for course for me, and that's cool. After lunch, I went down to the ground floor sat in a chair in the rotunda and fiddled on my phone, checking for emails for little over twenty minutes while people came and went without taking notice of my attire, and that made for a good feeling. With twenty minutes remaining on the parking meter, I left the building and casually strolled back to where my car was and returned home to watch football.

Another successful outing, one made all the better thanks to the new footwear I sported as I enjoyed those Payless booties I wore which looked good on me and the skirt I wore. There's no doubt in my mind I'll be wearing them more with fall here and winter on the way. More to come....

I've ventured to numerous places in heels, skirts and the occasional dress: shopping malls, city parks, crowded downtown areas, bookstores, big box electronics stores, restaurants and museums, all in broad daylight, and I've never had any problems, not even in 15 inch minis or five inched heeled thigh boots. In fact, every now and then, I get compliments on my attire from perfect strangers which is always a good thing. It's important to dress appropriately for the surroundings you happen to be in and to blend in as best you can, if you manage that, then you'll be accepted for your presentation. Something else to take into consideration is that ninety-nine percent of the people you'll encounter while out and about are often too wrapped up in their own lives and affairs to care about a guy in high heels, so, just relax, take it easy and enjoy the experience!

Very nice, Mr. X! Very nice indeed! The ankle boots are quite sharp. Perhaps I might invest in a pair, what with fall on the way.

14 hours ago, inquisitor said:

Christian Siriano "Phoebe" Ankle Boots:

Very nice indeed. How's the fit on them?

inquisitor: How's the fit on the "Haddie" and "Habit" shoes? Are those in wide width? Are they roomy or snug?

6 hours ago, Thighbootguy said:

Look around in the shoe accessory section for some adhesive inserts for the heel.  These are a soft rubbery material that is stuck in the rear of the shoe and provides some comfortable grip on your heel that keeps you from walking out of your pumps.  I have these inserts in a pair of ankle boots that tended to let my foot escape without them.  I think the issue is in shape of the heel area as some shoes grip your heel firmly and others let you heel wander around.

 

Yes, those inserts are well worth giving a try. I use them myself and they work as advertised.

TBG: Regarding your question about the art I had seen on Saturday, yeah, there were lots of stuff I liked, but wow, talk about expensive!

heelsrus2000 & bluejay: Thanks for the kind words on my latest outing and what I wore. Much appreciated.

TBG: Heh! Clever! But, Dallas Cowboys cheerleaders? Bah, humbug!

Jaunt #333, 9/18/2016: Despite overcast skies, temps were mild enough to run a couple of errands before the day's NFL action, heading out to Springfield in a brown t-shirt, a tan 20 inch Old Navy skirt, the Payless "Margarita" low wedge slides in natural and a matching handbag. Nothing fancy, just a simple, thrown together outfit to do a little running around in, especially the shoes (which I also have in black) which were comfortable and easy to wear, and, like all the other slides in my collection, I enjoy wearing them.

My first stop was to Acme to buy a few odds and ends, no big deal. Stop number two was down the road to a CVS drug store to buy a newspaper as the supermarket was out and a bottle of lens cleaner for my glasses, while waiting in line, an old man who looked to be in his seventies, perhaps his eighties, cane and all turned around to smile at me and said, "I saw you in the aisles, and I think you have the most gorgeous legs I've ever seen". To say the least, I didn't see that compliment coming, least of all from a man, now, that gentleman was wearing glasses, for all I know, he might've mistaken me for a woman, even though we were separated by little over a foot, still, it was sweet of him to say what he did, I smiled and told him as much, he chuckled and wished me a good day before walking off. I guess that wearing a short skirt does have its advantages. My next stop was to Best Buy to snatch up a copy of Captain America: Civil War on Blu-Ray, then, with some time to kill, I drove to Springfield Mall and wandered about for little over twenty minutes, as usual, no stares, long looks or double takes, I've kinda gotten used to that lack of attention by now. Perhaps the sight of a guy in a skirt truly is no big deal.

To any and all fashion freestylers here, I can't state enough the importance of dressing appropriately for the surroundings you happen to be in, not to mention giving the appearance that your attire is no big deal. If you do, chances are excellent that you'll be accepted as just another person, even if you do wear clothing and/or shoes tailored to the fairer sex. After all, guys have every bit as much of a right to wear skirts and heels as women, the key thing is to wear is to wear those articles with pride. More to come....

4 hours ago, heelsrus2000 said:

Jeff, I  hope people's critiquing hasn't disrupted your jaunts as its been 2 weeks and the thread is calling out for another ensemble. You should try bias cut skirts. Sassy as a pencil but a flattering flare to the hem. There should be a few on ebay  looking forward to your next jaunt  

Nahhh, not at all. I've just been busy, and, it is football season which takes up my time. Meanwhile....

Jaunt #332, 9/17/2016: Ahhh! Gotta love a pleasantly sunny day that's warm but not obscenely hot like it had been during the summer, the sort of day that's tailor made for an outing, and, with that in mind, I headed out in a black blouse, one of my below the knee skirts in olive, the Payless "Sinclair" platform wedge sandals in black and a black handbag. Confession time: I sorely regret not having discovered the joys of wearing slides and sandals years ago, I'm just crazy about wearing such shoes, in fact, during this spring and summer, I've worn them on 22 out of my last 25 outings, pretty impressive for shoes I once hated, but today, I love how good slides and sandals look on me, and, there were no other shoes I wanted to wear. I look forward to continue wearing them until the weather turns chilly after fall arrives. Anyhoo, I took great pains to put together a nice outfit that I'd both look nice in, and, more importantly, FEEL nice in, and I certainly accomplished that goal, and that's why I enjoy being a fashion freestyler.

I headed into town and my favorite hangout there, Rittenhouse Square Park, but it was much more crowded that usual for a late Saturday morning as there was an art fair going on, something like three dozen or so stalls where artists from as far away as Florida, California and Toronto, not to mention local talents had set up shop to display paintings, etchings, sculptures, you name it, and it was utterly fascinating, and I spent well over half an hour casually wandering from booth to booth to gaze at all the artwork, and it was a delightful experience, enjoying a little outdoor culture which was certainly a good thing. I won't bother to yammer about how no one paid any attention to my attire, because no one did, and that was cool with me as people accepted my appearance. With time ticking down on my meter, I returned to my car and drove out to Sugar House casino which is not as far away as Parx, I had only been to Sugar House a couple of times, but it's a nice place to come to in order to spend a few dollars, but after I had lunch an in-house eatery prior to hitting the one cent slot machines, going ignored there like at Parx while everyone focused on the one arm bandits they were playing. I didn't win all that much since I didn't spend much, just forty bucks, but I managed to win about sixty, nothing to write home about, but it was still fun, and I can use those meager winnings to buy groceries, so it's a win-win situation for me, a nice end to a nice day. More to come....

Well, I wear women's clothes from head to toe on my outings which tend to be infrequent. As for shoes, I've worn everything from flat sandals to five inch heeled thigh boots. Perhaps that makes me a 4 or 5.

19 hours ago, Thighbootguy said:

Folks; 

Considering the pictures that @CAThas shown us over the past months, this is an amazing statement of growth in self confidence that we should all take to heart.  How many of us have said, "CAT looks great but I could never do that"?  Admittedly CAT has a good figure and great legs but if he started heeling "in the darkness of night" and has progressed to his current " I just don't care what people on the street think", this should be a goal for all of us.   Not that we all present in the style CAT chooses but rather we have the confidence to present our own style.

 

@hiheellover23 - Great look and great shoes!

I like to think I've also progressed to the point when I can wear what I like, where I like, and no one gives me so much as the time of day because I've gone to great pains to present a proper image and show complete confidence in the outfits I wear. Without confidence, then we can't succeed in displaying ourselves in public, whether it's just in heels, or women's clothes from head to toe.

By the by, I agree that hiheellover23 does look sharp!

21 hours ago, Chorlini said:

I'm reminded of that show Hotter Then My Daughter, where they show a LOT of middle aged to older women are in serious denial that they can still wear the same (usually slutty) clothes that they did when they're young. They say age is nothing but a number but that is also serious denial. The sad fact is that while in our minds we still think of ourselves as the persons that we used to be when we were younger, the outside world is less forgiving. And there is nothing sadder looking then a man or a woman who still tries to look like a hot teen or tween. If you have good genetics or a healthy lifestyle nature will allow you to get away with it for a little longer then most, but when your face starts to look old it doesn't matter how lean, mean and trim your body is, it's just not going to mesh.

So I'm all in favor of dressing more age appropriately. Which in the minds of most people seems to be to give up and start wearing comfortable yet ugly as f*** clothing. But classy can be sexy in its own right too.

That is often, if not always my objective as I enjoy looking stylish and classy by dressing my age, and that makes me feel good.

On 9/7/2016 at 0:43 AM, bluejay said:

OK, JeffB on your ensemble, Sunday. The free flowing skirt looks nice but I like your look with the shorter skirts. I'm older than you and I'm told by my lady friends, that I look much better, wearing a much shorter skirt, about 4" above my knee. My legs are in good shape and I'm not afraid to show them off. So I take the positive comments from my lady friends who range in age from early 20's to late 60"s. Even my 19 year old granddaughter says I look nice, wearing a skirt. I also like to wear shorts, with heels, not short/shorts, but ones that are about, 4" above my knees.

I also only carry cross body bags, but I carry mine on my left side. You carry yours on your right side. You must be left handed, as I'm right handed.

Happy Heeling,

bluejay

Thanks for the kind words. While I'll admit short skirts look nice on me, I just love the longer ones which lend an air of elegance and style. As for the crossbody bag, I'm righthanded, since I'm so used to carrying a standard purse of my right shoulder, I just did that automatically.

21 hours ago, Puffer said:

Jeff:   I've just caught up with your recent jaunts - very impressive!   I do like flat women's sandals, although they are almost impossible to find in the UK in 'our' size (USW13/UK11).   Two questions if I may:

1.  Very few flat/nearly flat sandals from Payless seem to be available in a wide width - probably a cop-out by the manufacturer as they reckon feet can overhang sandals easily!   Yours mostly look a tad narrow - is that the case and does it bother you?

2.  Like you, I have a Nook e-reader (Glowlight), acquired about 2.5 years ago, and am very pleased with it.  (There is a good range of e-books for free download from libraries in the UK.)   But Barnes & Noble no longer serves the UK market and I am hoping that it will last a few more years at least without requiring any servicing.   Have you had any issues with yours, please?

 

To answer your questions:

1) Those flat sandals are in standard width, but, that doesn't bother me as they still look proper and don't overhang all that much, if at all.

2) I've had my nook e-reader since 2010 and it hasn't caused me so much as a moment's worth of trouble. I really enjoy using it.

7 hours ago, 5150PLB1 said:

Age is just a number on the scorecard of life. What counts more is attitude, health, an how you look and feel in what you choose to wear. If you have good health, have a positive attitude, look and feel great wearing your heels and clothes,  then age becomes irrelevant.

I agree wholeheartedly!