JeffB

Thanks for the compliments, everybody. However, I must admit I'm not sure how to react to the notion of being mistaken for a female with short, grating hair. HA! If that's the case, then there's a whole lot of people out there who need to visit their friendly, neighborhood eye doctor! Double HA!

19 hours ago, Thighbootguy said:

Great look JeffB!  The necklace and watch finish the look.  However to really improve the look drink a lot more Iced tea and a few less bacon mozzarella burgers.

So noted. But, I only had one burger. 

18 hours ago, Steve63130 said:

Very tactfully stated, TBG!

Nice outfit, Jeff.

Steve

Thanks for the kind words, Steve.

17 hours ago, SF said:

Or at least try the chili at Wendy's, it's very good.....   sf

I'll keep that in mind for the next time I visit Wendy's.

Jaunt #320, 6/26/2016: Sometimes, I feel as though every outing I undertake is another chance to push the envelope in terms of what I like to wear versus what society deems I be required to wear because of my gender. No big deal, I can grasp that, but it doesn't mean I have to conform to what society demands, because I don't. Case in point was yesterday's outing as I decided to wear a dress, nothing particularly fancy mind you, just a navy blue, short sleeved, Land's End knit frock with a breast pocket that I bought at Sears some two years ago, but never got around to wearing until yesterday. The dress came with a matching cloth belt and had side loops for same, but I didn't like it, so I replaced it with a thin white belt and paired it with the Payless "Stacey" low wedge sandals in white and a white handbag (yes, I still subscribe to the fashion tenet that one's bag must match one's shoes). Funny thing about the bag, I found a receipt in it from Boston Market dated 6/1/2014. Clearly it had been some time since this bag had been outside.

Even though the dress was a knit, it was still light and airy and comfortable despite plenty of sunshine and temps that reached into the upper 80's, more importantly, it was a treat to wear as I headed west into Springfield and Bed Bath & Beyond to buy a new cushion for the chair I sit in while at my computer to type these words of wit. Unlike my expeditions on skirts, I fully expected odd looks regarding my attire from other shoppers, but, nothing, not even from some little kids roaming the aisles with their parents. After making my purchase, I head back into town and stopped at Starbucks in University City where I had a cup of iced tea and some crumb cake while I read a book (The Adventures of Sherlock Holmes) on my nook e-reader. After little over an hour or so, I headed downtown and to Rittenhouse Square Park, my goal to be seen and gauge reactions. That proved to be a flop as even though the park was packed as usual for a Sunday afternoon, no one gave me so much as a glance, first, second or otherwise as I wandered the park until I found an empty bench in a shady area and continued reading for something like an hour an a half as people came and went, paying me not so much as an iota of attention. I found it cool that I loitered about in a dress in public and garnered no reaction whatsoever.

Meanwhile, it certainly felt good, damn good to wear a dress, better in some ways than a skirt, I experienced a sense, a feeling of, well, freedom because I was garbed the way I wanted. I was comfortable and completely at ease in how I was attired, and isn't that what fashion freestyling is all about? In addition, when I wasn't reading, I was subtlely people watching, mainly women and the seasonal dresses they wore, all the time wondering if I could wear outfits similar to them. Already, I'm thinking about how I could make sleeveless dresses (which I saw a lot of during my outing), maybe even sundresses work as part of my repitoire. I'll just have to see what I can do on that score. More to come....

On 6/22/2016 at 5:54 PM, heelsrus2000 said:

My pleasure! Last week, I met up with a member on another Forum who is really into his heels... A bit of a change from the old skirt in the mirror look. Don't worry,  I will look for a better wig

Well, I should hope you do! Just kidding!    Meanwhile....

Jaunt #319, 6/25/2016: Ahh, summer! A delightful time of year for being out and about on jaunts, especially when it's not overbearingly hot outside. Another thing about summer I've come to appreciate are girls and women who break out an incredible myriad of flat sandals for casual wear, and since I occasionally parrot what the fairer sex wears, I took a pair of flat sandals of my own, the Payless "Paprika" out for a spin, pairing them with a purple shirt with a lace applique in front, an Old Navy 20 inch dark denim pencil skirt and a black handbag. Right away, I felt perfectly at ease in the sandals which were comfortable and easy to wear, and looked good with the outfit I wore.

Didn't do too terribly much, I swung by my friendly neighborhood comic book shop for a good twenty minutes, bought a newspaper then drove over into South Jersey where I had lunch at Wendy's (their bacon mozzarella burger was good) then went to the multiplex at Moorestown Mall to see Independence Day: Resurgence. That was perhaps the only blech part of the day since the sequel to the film that launch Will Smith's movie career (no, he wasn't in the new film) wasn't all that great to me, still, there was a pretty good crowd in the theater where I watched the film. The multiplex was packed to the gills as is usually the case on a Saturday afternoon, I did get a few quick stares here and there, but nothing more than that. However, I did a thumbs up from a young woman who grinned at me in passing, and I appreciated that.

While it's always nice to be appreciated, what I like more is to be able to come and go as I please in the clothes I enjoy wearing with any muss or fuss from the public at large, and that's what my adventures have been all about from the time since I launched this thread. More to come....

3 hours ago, Thighbootguy said:

Probably not, but if they did here is a likely choice of footwear:

(Here is the link to these boots: Furry Boots

Wow! That's something! They sure would keep you warm in winter!

On 6/20/2016 at 3:35 PM, heelsrus2000 said:

I am lost for words!  Nailed it with this outfit!  Youthful, chic I love the skirt with the frayed hem ♡♡♡ frayed hem mini's are in this season, I have to go to Primark and buy one myself  best look so far this month  

Thanks for the kind words. Much appreciated!

On 6/14/2016 at 2:02 AM, heelsrus2000 said:

Loving both pics, I think the first one is my favourite.  Great contrast of colours. There is no reason why guys should wear such drab clothes and you prove that time and again !

I love the wedges in your black skirt combo ♡♡♡

Thanks for the kind words. Much appreciated.

Jaunt #318, 6/19/2016: Originally, I was going to dress up for today's outing and go to the Philadelphia Museum of Art, but then, laziness set in and I decided to opt for a more casual outfit for a casual outing, going with a black tank top with a 17 inch gray denim skirt with a "distressed" (fringed) hemline, the Payless "Stacey" sandals and a black handbag. The skirt, which I bought from Primark at the King of Prussia Mall on Saturday intrigued me considerably when I saw it, having seen young women and girls wear variations of fringed skirts, I decided to give one a try because I thought it would look good on me, sure enough, it did, especially with the black top I paired it with. And while I could've opted for wearing heels, that outfit screamed to be worn with my (relatively) flat sandals.

Even though it was sunny and rather hot, I felt perfectly cool and and comfortable, the skirt was so light, it felt like I wasn't wearing anything at all, and the (relatively) flat sandals complimented the outfit well, in fact, it felt pretty darn good NOT to be wearing heels. I only made two stops, the first was to Starbucks in the University City area where I spent an hour sipping on a tall iced tea while reading an e-book on my nook e-reader. My second stop was to what's become a regular haunt, Rittenhouse Square Park, as usual for a Sunday afternoon, the park was packed with people as I casually strolled the area looking for a bench to sit at and read some more, once I did, I sat and stayed there for nearly an hour and a half, and the only person who gave me an odd look was a homeless man, but then, he wore a heavy jacket, wool hat, sweatpants and combat boots, so perhaps he looked odder than me.

If I took anything away from this outing, it was that (relatively) flat shoes like I wore certainly do have a place in my wardrobe. I won't deny that I'm hooked on sandals of all heel heights and plan to wear them more over the course of the summer. One other item of note: nothing beats wearing a short skirt on a really hot day to keep you cool, I plan to do that more often too. More to come....

12 hours ago, Puffer said:

 

This throwback to the absurd glam-rock fashions of the 1970s does heel-wearing men no real favours.   Anyone wearing sparkly platform boots will likely be ridiculed in anything other than a narrow club environment.   And the Vogue quote '“This is also a celebration of our homosexuality,” said the designers.' will surely add ammunition to those who equate heels on men with a gay lifestyle.   

Totally agree. That comment does no favors to heterosexual men who happen to enjoy wearing heels. If anything, that reinforces an old and tiresome stereotype that needs to be eliminated.

9 hours ago, Thighbootguy said:

Looking good JeffB!  The belt matching the sandals ties it all together.  The watch is a nice touch.  And as for going out in a thunderstorm... we wouldn't want you to melt now would we?  The casino does sound like a great heeling place and coming out with $70 isn't bad (considering that you went in with $100).

Well, actually, I went in with $60 bucks, so it wasn't too terribly bad an outcome.

Jaunt #317, 6/12/2016: Sometimes when Sunday rolls around and I go on an outing, I love to dress up and look sharp, then there are other times when I prefer to be perfectly casual. Today was a sterling example of the latter as I wandered out to Springfield to goof around in a red t-shirt, a 19 inch button down denim A-line skirt, a recent acquisition from Payless, the "Stacey" sandal in black with 1 1/2 inch wedge heels and a black handbag. The skirt, which came from a store called Primark was light and airy and it felt like I wasn't wearing anything at all, and with the weather being very warm again, I was delightfully cool and comfortable in it. As for the sandals, I liked the styling when I saw them on the website, also, I was looking for a pair of low heeled sandals for casual outings, I found the Stacey shoes comfortable and they matched well with the skirt. Wearing sandals has become my passion and I want to experience both high heels and low.

My first stop on what was mostly a brief outing was to Acme to buy a couple of odds and ends, the store was plenty crowded as it was just after twelve noon, but no one paid me much attention as I did my shopping. From there, it was time for lunch and I traveled barely a block to Arby's where I had a Beef & Cheddar sammich with a bottle of water. Tasty! My next stop was to my home away from home, Best Buy where I chatted with a salesperson about the latest evolution in high definition TV and the fact it was a tad pricey, but hey, it costs nothing to look, and I so do love gazing at gadgets and gizmos, that too is a passion. After checking out with a goofy sounding horror flick called Navy SEALS vs. Zombies (boy, I can't wait to watch that), I headed down the road to Office Depot, my last stop of the day to buy a ream of paper for my printer at home. As was always the case, I felt perfectly at home in my attire, in fact, it felt darn good to go casual for a change, and those new flat sandals I bought were a treat to wear.

All things considered, I guess this means I'll have to indulge in more casual Sunday outings which, in their own way, were plenty fun. More to come....

Dang! Size 19? Those aren't gunboats, we're talking aircraft carriers! I never thought women's shoes came THAT large!

Hey there, Mr. X! Cool outfit! The all blue theme worked very well. Congrats!

Jaunt #316, 6/11/2016: Just a short outing of sorts because of the threat of early to mid-afternoon severe thunderstorms, but I still went out, even though it was sticky and steamy, garbed in a sea green top with lace trimmed sleeves, a black denim pencil skirt, the Payless "Sinclair" platform wedge sandals in black and a black handbag. Regarding the sandals, I had previously worn a pair in navy and liked them so much, I got them in black/ Yeah, I think it's safe to say I'm pretty much crazy for sandals, I've really come to love wearing them, and, at this time of year, I can't imagine wearing any other shoe. So, perhaps I'll indulge in an experiment where I'll wear nothing but my slides and sandals throughout the spring and summer.

My first stop was to the main branch of the Post Office to buy a money order, the line there was a tad longer than usual, but I didn't mind waiting, other than an elderly Asian woman, no one gave me so much as the time of day. After making my purchase, filling it out and dropping it off, I got back in my car and headed into the greater northeast and Parx Casino to spend a few sheckels on the one-arm bandits. However, before that, I had lunch as it would be foolish to gamble on an empty stomach, then I went about fooling around on the slot machines. Despite the brightly colored top, snug skirt and heeled sandals, I was ignored as everyone was busy pulling those slot machine handles to pay me any attention, as has always been the case when I've gone there. As I've said before, casinos/slot parlors are a great place to go heeling because no one cares what you wear. As for my battles on the slot machines, well, it was nothing to write home about as I spent a good couple of hours there, but only managed to leave with around $70 bucks or so. But, hey, I go there to have fun, and that's good enough for me.

The traffic back home was miserable because of road construction jamming things up, but what really annoyed me was that those afternoon thunderstorms never materialized, meaning I could've stayed out longer. Oh, well, them's the breaks, still, I did enjoy my outing, and that's the important thing. More to come....

Whoa! I have influence with people? Who knew? Anyway, neat shoes there, TBG, they look nice when paired with your outfit.

Another new pair of shoes from Payless, the "Havana" block heel sandals. Very snazzy looking and stylish, goes well with skirts.

13 hours ago, heelsrus2000 said:

What a fantastic ensemble!  The turquoise really suits you ♡ people were probably staring as they were so jealous   nice skirt as well and I have to invest in some slides like that, but I fear not tanning my feet properly and having strap lines of lighter skin crisscrossing my feet  

I have to see Captain America when it's released over here in the UK. You always look so composed when you model your jaunt ensembles, I am surprised that you have never been tweeted or appeared on social media,  but I guess people must really accept fashion freestyling nowadays. A picture of you whilst actually out on your jaunt at the mall would look even better and encourage more to embrace heeling and fashion freedom!

Still, looking forward to your next jaunt 

Thanks for the kind words. Yeah, I tend to think turquoise works well with my skin tone, and it's a fun color to wear. So far, I've yet to encounter problems with strap lines of shoes. Speaking of which, just wait until you see the shoes I wore on my latest outing!

6 hours ago, bluejay said:

Nice look JeffB. Finally the summer heat hit here too. Spring disappeared in a few short days. A couple weeks ago we were looking at snow flurries. Record heat on Friday and Saturday, a little cooler today only about 88*, but still very hot for this time of the year.

With Memorial Day here, it was time to break out the white. I wore a 20" white skirt, Saturday night, with a royal blue polo shirt and my new Aerosoles , "Light N Sweet" white leather, wedge heel, slides. I carried my Vera Bradley, multi colored floral, cross body bag. I got a nice compliment from the woman sales associate, at the Land's End kiosk, in the Sears store, who has seen me wearing heels, many times.

Today, I wore a hot pink 20" skirt, with a white polo shirt and again the Aerosoles, white leather wedge heel slides. Today, I matched the shoes with a white leather, cross body bag.

Having recently returned from a vacation, my legs were nicely tanned and I did look good wearing my skirts. Any yes the comfort level on a hot sticky day, wearing a short skirt, is a great way to go, for us men. A skirt is so much more comfortable than shorts.

Hope everyone has an enjoyable Memorial Day, here in the USA.

Happy Heeling,

bluejay

I appreciate your compliment. Ahh, yes, Memorial Day, most definitely time to break out the white. I'd do so today, but we're going to have periods of rain throughout the day. Oh, well, there's always next weekend. Meanwhile, two thumbs up on your outfit!

Jaunt #315, 5/29/2016: With Sunday being just as sunny and nice as the previous day, it was a good time for a new outing. But, unlike Saturday, I wanted to dress up, going with a black tank top, a black and white printed skirt, a new pair of shoes from Payless, the "Havana" block heel sandals and a black handbag. The skirt, one of three I bought at Sears two weeks ago checks in at 32 inches long, is light, airy, perfect for spring and summer, also, it's lined, a first for me, in short, it's a pretty skirt and I enjoyed wearing it. Then there's the shoes, plain and simple, I'm hooked on sandals and was most intrigued with these, especially the 3 1/2 block heels, something I've never worn before, I found the Havana sandals most stylish and paired well with my skirt. Altogether, it was an outfit I felt great wearing as I was proud of how I looked.

My first stop was to Micro Center, a computer store in the western suburbs to buy a new wrist rest for my computer keyboard, after finding what I wanted and wandering the aisles for nearly half an hour. Going to the registers, I was waited on by a petite Latina who, after ringing up my purchase, smiled and said my skirt was pretty, I grinned and thanked her for the compliment. From there, I returned to town and headed into downtown and my favorite haunt, Rittenhouse Square park, just like on Saturday, the park was filled to the brim with people enjoy the weather, I managed to wander through the park, ignored by just about everyone until I found an empty bench where I sat and proceeded to finish reading an e-book on my nook e-reader for well over an hour as people came and went, but no one gave me so much as the time of day as I sat and read. It was a great day to be freestyling in a crowded city park, something I plan to do more often as it's a great way to spend a pleasant afternoon. More to come....

Thanks for the kind words. My evolution as a fashion freestyler has made wearing women's clothing a great deal of fun as I've gone to great, almost obsessive pains to look the very best I can when out in public. And yes, when I am out and about, I'm wearing MY clothes, they just so happen to come from the women's side of the store. To openly challenge society's conception about what men are allowed to wear has been most fulfilling, when people see me, I want to force them into the realization that not only don't I look odd or freakish in the clothes I choose to wear, but that I look good in them as well. Proper and tasteful presentation is EVERYTHING to me, and if I can display to the world at large that men CAN look good in skirts and heels if done correctly. And that's a mission I undertake to the very best of my ability with each and every outing.

New sandals, the "Sinclair" platform wedges from Payless. It's crazy how I've come to love sandals, and these shoes with their four inch heels both look great and feel great to wear.

Thighmax: Thanks for the kind words. I'm just doing the very best I can. I'm glad folks like you appreciate my efforts.

Jaunt #314, 5/28/2016: A couple of weeks ago, temps here struggled to crack 60 over the weekend, yesterday, we saw a high of almost 90. NINETY! In late May. That's the problem with living in my neck of the woods, spring lasts about a week before we go directly into the microwave. Anyhoo, the heat didn't stop me from going out for the day on a jaunt, attired in a turquoise blue top with lace style sleeves, my Old Navy 20 inch khaki skirt, my new Payless "Sinclair" platform wedge sandals in navy and a black handbag. The top, which I bought from Sears was so cute, I bought it in three other colors, black, red and sea green, as for the shoes, they were also cute, fit well and were comfortable. At this time of year when the weather is warm, sandals are really fun shoes to wear, and my passion for platform wedges made those shoes a treat.

My first stop of the day was to the main branch of the city's Post Office to buy a money order, there was a bit of a long line as there were half a dozen people ahead of me, I did get some long looks from a couple of Latino kids waiting with their parents nearby to have passport pictures taken. Those kids were both wide-eyed and puzzled at my appearance, when I grinned at them, they turned away. Oh, well, them's the breaks. After buying my money order, I left for downtown and my friendly neighborhood comic book shop where I spent some twenty minutes, then headed down to Rittenhouse Square Park, even though temps were already in the 80's, I felt perfectly cool and comfortable in my short skirt, the airy feeling was most delightful, something I wouldn't have experienced in long jeans or even shorts, again, it makes me wonder why more guys don't wear skirts to keep cool on exceedingly hot days. The comfort that comes from wearing them is real and considerable. As usual for a sunny late Saturday morning, the park was bursting at the seems with people, none of whom paid me any attention as I casually strolled about until I found a bench and sat down with a paper to read and just enjoy the surroundings for nearly an hour. Being in the park is great fun for me as I get to people watch and be watched.

Returning to my car, it was off to South Jersey and the Moorestown Mall area where I had lunch at Wendy's where I was ogled at by several young teens in baseball uniforms, while I did get a couple of giggles, that was pretty much it. After that, it was off to the nearby multiplex to see Captain America: Civil War, had to stand in line for nearly ten minutes, earning me a few stares, but nothing came from that, after buying my ticket, it was off to the men's room to take care of business where I got a long look from an older gentleman who looked somewhat irked, but didn't say anything. As for the film, WOW! It was great! I recommend it highly! Casually walking through the main lobby after the film, I got some more looks but ignored them as I headed back to my car to return home. I think this outing represented the most looks I've gotten on an outing in awhile, but it was no big deal, still, it would've been cool to have interacted with anyone who wanted to engage me in conversation about my attire, but that didn't happen. Speaking of cool, short skirts are definitely a must on hot days in order to be comfortable, and I plan to wear mine more in the future. More to come....

Time for a confession: I'm a man who loves wearing women's clothes...as a man. Perhaps that makes me a crossdresser or a transvestite, but I don't need to don a wig, put on makeup or strap on a padded bra, just the act of wearing the clothes alone is more than enough of a thrill for me. To wear a skirt or a dress is positively exhilarating; to hear the clicking of high heeled shoes on my feet is intoxicating; and the heft of a full handbag on my shoulder is pleasurable. And the fact that I venture out in public garbed in women's attire from head to toe is exciting in ways I can't possibly describe, and, heaven knows I try, real hard. This is the true extent of my existence as a fashion freestyler, and I love every minute of the experience.

As everyone here knows from my years as a member of this board, my special journey started with just the shoes, and, in the beginning, I thought that would be enough to satisfy me, but, as time went on, I came to realize that wearing my heels with men's clothing, dull, boring and hopelessly static wasn't enough, I needed more. That was when I ventured into skirt wearing in the latter half of 2008, more of a crazy personal dare than anything else, that first outing in a simple denim skirt (which I still have, by the way) was fun for me, mainly because of how the skirt looked on me, and how I liked what I saw, from that moment on, I started integrating skirts into my jaunting routine, they looked good on me, and I desired to wear them more, going with various lengths, short, knee length and maxi length, pairing them with pumps and boots, that was the beginning of my exploration into fashion freedom, but even that wasn't quite enough since I was wearing men's tops with the skirts and footwear. I decided I had to branch out more to satisfy the demands of my thirst for fashion, to see just how far I could take this sartorial passion that was welling up inside me, and I wasn't about to stop.

That inevitably lead to women's tops: sweaters and turtlenecks in fall and winter, and when spring and summer came around, t-shirts, blouses and my favorite, tank tops. Again, I wouldn't wear such articles of clothing if I didn't think I looked good in them, and, being rather critical about my appearance, I made damn sure that I was happy with my appearance, otherwise, I didn't leave the house. Period. Hosiery was already part of the equation as I often wore knee highs under my pants and jeans, but when I gravitated to skirts, pantyhose became a must, followed by tights to keep my legs warm in winter. At the risk of sounding egotistical, as good as my long legs look bare, they're sensational when I've got hose on. Purses and handbags were next as part of the evolution since pockets on skirts were small, and it looked gauche to stuff items like my wallet, keys and smartphone, just to name a few items into them. Another confession: early on, I'll admit to being more self conscious about being seen with a handbag than I was about wearing a skirt and heels, but that anxiety quickly faded. In fact, and I've said this more than a few times, I don't feel dressed without a purse.

The final part of the equation were dresses. Since I was already comfortable in tops and skirts, able to go practically anywhere I saw fit without encountering any unpleasantness, I thought it was time to push the envelope by going out in a dress. That first outing was in a sleeveless black sheath from Sears with a blazer and a pair of heels, that journey was most enjoyable, mainly because I went out of my way to look the very best I could, and, having achieved that goal, I realized that I looked good in that dress, and that filled me with plenty of confidence to brave the outside world. That lead me to wearing dresses whenever I could, one of my more pleasant outings was in a black cowl neck sweater dress with hose and a pair of high heeled knee boots, and, to say the least, I looked damn sharp that day. Since then, I decided to integrate dresses more into my repertoire. The bottom line here is that there is something incredibly special about wearing women's clothes in public as a man, it says I'm bold enough to ignore gender assignation when it comes to clothing and wear what I like, not what society says I should. And I fully appreciate that special brand of boldness.

There's a true wonder to women's clothes, the colors, the styles, the fabrics, how wearing them helps me feel softer, gentle and happier while putting me in touch with my feminine side. I can't help but feel uplifted when I wear these clothes, like they put me on an entirely different plane of existence. I never fail to feel elated when I come and go as I please, dressed how I like without any trouble or negativity, I believe that because I go out of my way to present the utmost when it comes to a tasteful and proper image, people accept me for my appearance, or choose not to bother with me, nevertheless, I'm pleased. Now, I have to stress that not everyone can, or should do what I do, perhaps I'm an anomaly, a rarity when it comes to the concept of men who choose not to be constrained by the clothing and footwear society demands we wear. I'm extremely proud to be one of those men who've fully embraced the concept of fashion freedom, I take tremendous pride in wearing women's clothes, and letting the world see me in them. And the feeling is wonderful!

Very nice, Mr. X! As a recent devotee of sandals, I like your shoes in particular. How high are the heels?

Not bad, TBG! You certainly seem to have embraced platform sandals.

8 hours ago, Thighbootguy said:

Hey, remember the sacrifices we have to make for fashion.

HA! I'll take that under advisement! 

10 hours ago, Thighbootguy said:

JeffB;

The outfit looks great.  I think the denim jacket is a little too casual for the overall look and that the black leather one would have worked a little better.  Stylish, fashionable, tasteful... all seem appropriate but I don't think I'll go as far as "cute"; but its nice to a complement.

Regarding my decision to wear the denim jacket, it was too cool to go with just shirt sleeves, but too warm for the leather jacket. As with everything, it was all about experimentation to find something I thought that would work. For a situation like that, perhaps a blazer would work better. I'll see about obtaining one. As for being called cute, that did kinda take me by surprise, but hey, a compliment is a compliment.

5 hours ago, heelsrus2000 said:

I would agree with TBG that it is not exactly "cute" unless the lady in question was being facetious I think a nice ladies mac (raincoat), one of those lightweight ones would have completed the outfit for a more demure look. The denim is very casual, although double denim  (the jacket and similar denim skirt) would look good together. The skirt is very formal, IMHO. Though a similar printed pencil skirt would go with the denim top

No, the lady in question was being genuine, I could tell. Meanwhile, wearing a printed skirt was fun, I'll have to do that again in the future.

Jaunt #313, 5/22/2016: Unlike most outings, this was mainly a spur of the moment trip as I had a crazy desire to put on a skirt and a pair of heels and go out, nothing more, nothing less, and out I went in my denim jacket over a black tank top, a dressy printed skirt that fell below my knees that came from Sears, the Payless "Karmen" pumps in black matte and a matching handbag. The outfit was highlighted by the skirt which was light, airy and easy to wear, a step above casual, thus my having worn pumps instead of say, the O'Malley slides, and it allowed me to dress up just a bit, and there's nothing wrong with dressing up on a Sunday. With no particular place to go, I drove downtown, parked some two blocks away from Rittenhouse Square and strolled to one of my usual spots, Barnes & Noble, on the second floor was the cafe where I bought a sandwich and a bottle of water and sat down for well over an hour as I ate and composed a new thread for the forum about women's clothes on my iPad. The whole time, no one paid me any mind as I sat at the table and typed away, time well spent to say the very least, and most enjoyable to boot.

After that hour had passed and I typed the bulk of my little treatise, I packed up and left the cafe, down on the main floor, I poked around the magazine section when a plump black woman in her mid to late twenties looked me up and down then said to me that my skirt was pretty. When she asked where I bought it, I told her it came from the Sears store in Moorestown Mall, I added that I bought it a year ago and didn't know if it was still on sale. The woman looked a bit disappointed but said she'd go there one day and look, before walking off, she smiled and said I looked cute, I smiled back and thanked her. How about that, here I was, a 57 year old man with graying hair called cute by someone, needless to say that came as quite a surprise, but a pleasant surprise. One more example of how all the hard work I put into assembling a stylish, tasteful and proper image of a man in women's clothing produced a positive result, a goal I long sought for myself as a fashion freestyler. As I'm forever fond of saying, I guess I'm doing something right, and having fun wearing the clothes and shoes that I love at the same time. More to come....

I don't think I've mentioned this, but April 28, 2013 marked the last time I've worn jeans or pants on my outings as it's been all skirts (and the occasional dress) ever since, and I've never looked back, never had a reason to. Even early on in my initial outings in skirts, I quickly realized how good I looked in them, how much fun they were, and that fueled my desire to wear them more and more. Everything from 15 inch minis to a 40 inch floor sweeper, I just love wearing skirts of all kinds, styles, fabrics and colors, and I'll never stop wearing them!

Just to add my two cents worth, I don't think you should actively try to "shut off" your emotions when it comes to doing what you love. In my opinion, that would lead to frustration and disappointment when you find that you can't, in other words, just go with the flow. While I don't wear the sort of sky high platforms you do, I'm every bit as much "out there" because I wear skirts and dresses in public, yet, I never worry about how I'm perceived, I just go about life doing what I enjoy, that's all any of us can do. Take things one day at a time and you'll be fine.