JeffB

Oh, wow! Those sandals are seriously sharp! I'd wear those in a New York minute! Well done, my friend!

Hmm! I'm that predictable, eh?    Meanwhile....

It's time for the Sunday Doubleheader!

Jaunt #284, 9/6/2015 (morning): Around eight a.m., I went to the supermarket on my weekly grocery run in a brown t-shirt, an Old Navy 19 khaki skirt, the Payless "O'Malley" slides in brown and a matching handbag. There wasn't much of a crowd at that early hour which is when I always do my shopping, the place was quiet with not many shoppers, and what few people that were there paid me no mind as I went about my shopping, and it felt relaxing to simply go about my business, and, thanks to coupons I clipped the night before, I managed to save a few dollars on my bill, definitely a good thing indeed! The only problem I had, per se, was the usual one when strolling through the frozen food aisles in a short skirt and having all that chilly air wash about my legs. BBRRRRRRR! Otherwise, a pleasant little outing.

Jaunt #285, 9/6/2015 (afternoon): With a few extra dollars at my disposal, I decided to spend them at Parx Casino, heading there in a black tank top, a 28 inch muted green plaid skirt I bought at Old Navy the day before, the "O'Malley" slides in black and a black handbag. Regarding the new skirt, when I saw it at the store, I was instantly intrigued, both by the pattern and by how light and airy it was, so I went ahead and bought it, and I didn't regret it as it was fun to wear. As usual when freestyling at a casino, it's quite easy to go unnoticed as patrons were too busy working slot machines to notice me, I arrived shortly after eleven and got right to work on a new penny machine on the floor based on the Sons of Anarchy TV show, and wouldn't you know it, I got lucky on the machine after some fifteen minutes as I won little over $100 bucks. Not bad, not bad at all. Not one to push my luck, I cashed out, got my money and fiddled on an old favorite, Sex and the City and won another seventy bucks or so after some ten minutes of action. Whoo! I then paused to have lunch, then fiddled another couple of machines before I decided to leave with my meager winnings. On my way to the parking lot, a black woman my age with her husband said she liked my necklace, then asked if I had any luck, I replied that I did okay and she chuckled.

From there, I headed back to the city and drove into center city, finding a spot a block away from Rittenhouse Square Park, I put five bucks in the meter and headed to Barnes & Noble where I renewed my membership, bought the newest issue of Sports Illustrated then retreated to the park, hustling and bustling and full of people thanks to sunny and mild weather, found a bench and sat down to read and otherwise relax. It was a great day to be in the park because it was so busy and full of people enjoying the day. After an hour and a half, I got up and left the park, passing a black woman about my age who said I looked nice, I smiled and thanked her, I walked two blocks down a crowded Walnut Street past people who didn't give me the time of day as I went to the Apple Store to check out the Macbook Air which I'm kinda interested in buying, despite it's rather steep price. After some twenty minutes in the store, I left and walked four blocks up the street to where my car waited and returned home. I'd say this was one of my more enjoyable outings, start to finish. More to come....

Hmph! I can't see the pictures either. Most annoying.

Oh, I never worry about stares. Since I know that's going to happen, I just do my best to take it all in stride.

TBG: Thanks for the kind words. Perhaps I'll wear more blue in the future. Admittedly, I don't frequent malls all that much while on jaunts, in fact, I think this past Saturday was only the second or third time I've done that, still, it was mildly interesting, if but for no other reason than the reactions. Will I do that again? Who can say.

Kilty: Perhaps the skirt was a tad long for the season, something like that would be more suitable for fall than summer, still, I enjoyed wearing it. As for looking out of place, well, I don't think that was quite the case.

Jaunt #283, 8/29/2015:

For me, outings are an opportunity to experiment with clothes and shoes, trying to decide what looks good on me and what doesn't. Yesterday was a day to experiment, going with a blue polo shirt with my knee length button down skirt in natural (beige), the Payless "O'Malley" platform wedge slides in blue/pink (I went with them as I thought they paired best with the shirt) and my black Buxton bag which I hadn't used in awhile. I rather enjoyed using that bag which is worn across the body, leaving my hands free. I thought the outfit worked pretty well, perhaps I may have been a tad overdressed for a Saturday, but that's nothing new with me.

My first stop of the day was over the bridge and into South Jersey where I went to the multiplex across from the Cherry Hill Mall to see Hitman: Agent 47. It was just before 10 a.m., but there was already a good crowd, so I earned a few gazes and stares as I entered the facility and stood in line to buy my ticket. In a darkened theater, no one can see what you're wearing, so I kicked back to watch the movie (based on the Hitman videogame) which I found to have been entertaining. After the movie ended, I earned a few more stares as I left the building, I hopped in the car and drove over to the mall and went to the food court for lunch. More stares here and there, especially from young kids and a few teens. Well, that was to be expected and, for the most part, I was used to it, but I wanted to gauge the reactions from people around me, and I wasn't disappointed as I wondered what those people noticed most: the skirt, the shoes or both? I would end up spending nearly an hour at the mall wandering about and it was interesting how some people took notice of me while most didn't, or, perhaps, chose not to notice.

Leaving the mall, I drove down to Moorestown Mall for a little shopping at Sears where I bought a couple of cute knee length printed skirts that I think will work very well for outings where I wanted to dress up, and they were on sale too! Cool!  I then walked through the mall, smaller than Cherry Hill to see if there were any stores that piqued my interest, there weren't, but it was still rather fun, and, yes, I did garner a few looks here and there. Since I don't cruise through malls all that often in freestyling mode, it was an interesting experience as I got to broaden my jaunting horizons, and that was enjoyable. More to come....

Some artist use a pencil, some use a paintbrush, some work in clay, and some use fabric and color artfully chosen and arranged into great looking outfits. 

 

A word of caution: A short leather skirt with thigh boots is a powerful image (but it is a LOT of fun).

 

TBG

Oh, I agree that does make for a powerful image, and that's why I want to wear such an outfit. I want to strut my stuff and demonstrate to the world at large that men can rock skirts, dresses and heels without actively trying to impersonate women.

That is one cool outfit, Jeff! You wear it well!

Thank you, SQ. Your kind words are much appreciated.

That is as you say Jeff, dolled up! Well done! I like the bag by the way.

Thanks for the kind words, Mr. X. Lately, I've recently arrived at the conclusion that a nice looking handbag fully completes an outfit. And it's fun to carry a purse!

JeffB;

 

I have previously commented that Pink was not your color.  Blue is your color!  That outfit is great and the accessories are well matched.

 

I'm glad you chose the Art Museum for your big outing.  The museum usually has a great group of people in attendance that are willing to accept something "different".  If hey weren't all the pictures in the Museum would look the same and only the people that liked that style of picture would attend.  Most art lovers appreciate diversity.

 

I remember your post about your last visit to the Museum and the fun you had.  Seems to me it will soon be time to go again back again in a short skirt and your thigh boots to add to the diversity of the patron's experience.

Yes, I would agree that blue does indeed suit me, and I took particular pride in the outfit I wore on Tuesday. Going on a jaunt at the museum was an absolutely amazing experience, taking in the art, even interfacing with other patrons makes me wish I had done this more often, but I plan to do so in the future. I had never considered myself as an "art lover" before, but I've come to understand what it's all about, and I truly enjoy it. With fall and winter in the queue, I'll be lining up future outings to the museum in a short skirt (perhaps a short leather skirt) and my thigh boots.

Thanks for the compliments. I guess one reason for wanting to change footwear come September or October is so I can break out my boots which I enjoy wearing, but I would agree with both of you that platform wedges have that certain style that can be worn all year around, weather permitting. I'll certainly investigate what I can about continuing to wear slides and sandals deeper into what's left of the year.

Could formal pencil skirts (not denim or chino) be on the horizon?

Oh, most definitely. I can see myself lunching downtown regularly in such skirts, especially dresses! Heh! Meanwhile....

Jaunt #282, 8/25/2015:

As everyone here knows, I'm a real nut about numbers, and since yesterday's outing marked my 200th in a skirt, I thought I'd celebrate the occasion by dressing up in a lace trimmed navy blue blouse, a 34 inch blue print skirt (both I bought at Sears over a year ago), the Payless "Karmen" pumps in blue patent, a matching Nicole Miller handbag and, to top off my outfit, I added my strand of pearls. Words can't describe how wonderful it felt to wear such an outfit which was as feminine as I could get, and I definitely felt feminine as well. Dressing like a woman is such great fun and I was proud of the outfit I put together to serve that purpose.

My destination for the day was the Philadelphia Museum of Art, the last time I visited there was a few years ago when I wore a white campshirt, a dark denim miniskirt and the Pleaser 4 inch heeled thigh high boots, but I opted for a dressier ensemble this day. Something else that was different was that the place was packed with people yesterday, including lots of young kids which kind of surprised me, however, that was no big deal, in fact, I looked forward to being seen and the reactions to my appearance. Guess what? There were no reactions, I was treated like everyone else in the place. As for the visit itself, the museum was most definitely a treat, so much amazing and remarkable and beautiful art to see, I was wowed from how terrific the experience was, and that included interfacing with folks here and there, none of whom paid any attention to my clothes, I especially enjoyed chatting with an older lady for a solid five minutes about European tapestries from the 16th century and if they had been displayed or walked upon. I wound up spending a solid three hours in the museum, and I'm not sure I had seen everything, but that's cool, gives me a reason to visit again in the future, heck, perhaps I might even become a member, that would be cool.

It certainly felt great to dress up for my museum visit, something I don't do all that often, given my penchant for casual attire, but I'm going to plot future outings where I get to doll myself up to the nines. This particular aspect of my freestyling will become more important to me over time. More to come....

Bravo on your latest outfit, Mr. X! Bravo! It's really sharp!

Once upon a time, say three or so years ago, you couldn't have paid me to wear either of the following:

--sandals

--slides

--platforms

--wedges

Of course, things have changed since then as I've fully embraced all of the above. In fact, since spring arrived in these parts, I've gone on 25 outings, 20 have been in slides or sandals, especially the former as I've fallen in love with the Payless "O'Malley" slides, they've been my go to shoes over the last couple of months as on many occasions, they've been the only shoes I've wanted to wear, and I thoroughly enjoyed wearing them because of their style, comfort and how easy they are to stand and walk in them, thanks to the stability of the platform wedges, as has been the case with the sandals in my collection. Needless to say, those seasonal shoes have paired wonderfully with my skirts.

I guess this qualifies as yet another paradigm shift in my continuing evolution as a fashion freestyler as I've come to realize there's more to shoes than just the enclosed variety (i.e., pumps and loafers) which I had worn religiously for years. However, with September right around the corner, and cooler weather to follow, my season of slides and sandals will soon come to a close, and a part of me will be sad about that. Still, once autumn and winter have come and gone and spring returns, I'll be eager to head out in my slides and sandals once more. Opinions?

We should take this as a warning to the world to look out for JeffB in a few years.  Being retired has a way of changing your view of yourself and the rest of the world.

Indeed! I'll be free to go jaunting as much as I want with no fear of any reprecussions or anything like that. I can't wait!

I got that.  But even 100% skirted on jaunts is a whole new level in my eyes.  Good luck!

Well, I've been all skirts (along with the occasional dress) all the time since late April of 2013, and it's been thoroughly enjoyable so far.

Take it to the next stage and tell the work place I'm sure that they would be accomodating

Nahhhh! I'm good. I only have a few years left until I retire, so I'm content to maintain the status quo. 

Heck, I don't know if ANYTHING you'd see models wearing on runways and catwalks can be worn in normal settings, not even on Rodeo Drive, Soho or the French Rivera, but that's just my opinion. While it does appear that gender bending is becoming more than just a fad when it comes to fashion, it's still a long way from being the norm, or whatever passes for same, and, I think that will only happen when more downscale designers start turning out clothing you don't need to take out a second mortgage on your house to afford. As for freestyler so like me, I'll be more than content to shop the Ladies aisle at Sears or JCPenney for what I need.

The Pope is visiting the comic shop?

Well done with your decision regarding bifurcated clothing, but how will going to work skirted be? Is the environment at work accomodating of freestylers or do you have any formal trousers for the office left?

It's a bold move but well done on making the decision you need some fitted dresses and formal skirts for the office

Freestyling is one thing Jeff. But you decision to go skirted all the time takes it to a whole new level! Good luck, and well done!

Oh, no! I meant to say I'm only going skirted on my jaunts. I'll still be wearing pants to work and such.

Jaunt #281, 8/22/2015:

The timing for my latest outing couldn't have been better as it came after several days of steamy and sticky weather that made being outside considerably less than pleasant. While sunny, it was less than humid as I headed out in a blue t-shirt with a lace front, my Old Navy 20 inch khaki skirt, the Payless "O'Malley" platform wedge slides in natural (a.k.a. beige) and a matching handbag. This outing also came after having made another important decision regarding my career, for lack of a better term, as a freestyler, a few days earlier, I had taken the six pairs of jeans I kept in storage to Goodwill where I donated them. This was a point of no return for me as I cut my last tie to owning any bifurcated outer clothing for use on my jaunts, from here on out, I'm truly, all skirts, all the time. And I wouldn't want it any other way.

Anyhoo, my first stop of the day was downtown and my friendly neighborhood comic book shop, much to my surprise, I found a parking spot only half a block away from the shop, got a stare from a couple of young kids, but that was it as I walked to the shop where I spent a good twenty minutes or so, chatting with the staff about sports and the visit by the Pope next month and how that would affect their being open on that last weekend in September. Leaving the shop, I walked around the corner to a newsstand where I bough a newspaper, then returned to my car and drove over the bridge into South Jersey and the Moorestown Mall area where I had lunch at Chick-Fil-A. The place was, as usual, fairly bustling as it was about 12:30 p.m., there were a goodly number of teens in the store, got a few stares, but nothing more. After lunch, I decided to take in a movie at the nearby mall, seeing The Man From U.N.C.L.E., it was pretty good but not great, still, it was worth watching, despite the less than stellar reviews it had gotten. My last stop of the day was to Best Buy and my (close to) weekly dose of ogling all things electric and electronic, finally leaving with the Blu-Ray version of Ex Machina which I had been curious about.

As usual, it felt great to wear a skirt, especially on such a warm day as it kept me nice and cool, despite the temperatures. As usual, the O'Malley slides were the first shoes I reached for when putting together my outfit, as I've said before, they're easy to wear and comfortable and, despite the four inch heels, it doesn't feel like I'm wearing anything even remotely that high, which is why I call them my casual wear shoes, and dressing casual for the surroundings I was in was important to me. More to come....

I found a pair of real leather Nine West knee high boots in a long toe style with a 3" stiletto heel in a size 12 for $17.  I didn't know Nine West made a 12.  I wore them to the grocery this morning and turned a few heads.  I thought the heel was lower than 3" but that's what they measure.

 

GEDC0156.jpg  GEDC0155.jpg

GEDC0154a.jpg  GEDC0153a.jpg

 

The long toe takes a little getting used to.  I don't notice the toe when I'm walking but I have sent several area rugs flying when the toe caught in the rug.

 

Nice boots, TBG! I must say they kinda remind me of my Payless "Tara" knee boots in terms of style, and the long toe. I've had those boots since 2008 and they still fit like a dream.

Speaking just for myself, I don't subscribe to labels when it comes to this subject. If I were to describe myself, I'd say I am a freestyler in that I'm perfectly content to wear women's clothes and shoes as a man, no wigs, no makeup, no false breasts, nothing like that. I'm the living example of my signature, "I don't want to LOOK like a woman, I just want to DRESS like a woman.", and that's more than good enough for me. I've never had anyone ask about my sexuality when out and about in the clothes I chose to wear, nor would I pretend to be something I'm not, I'm simply a heterosexual male who happens to love wearing women's clothing. If that makes me a square peg in a role hole, so be it.

JeffB;

 

Pink is not your color.

 

The pink top shows a lot of skin so you have to take your natural color into consideration.  I wasn't sure what was bothering me about the pink so I Googled "fashion color wheel".  A it turns out the  denim blue is close to a complementary color to your skin (so it looks great) but the pink is about 30 degrees away which doesn't really fit the practiced combinations.

Hmm! Most interesting. I read the article and understood what you were getting at in terms of the fashion color wheel. Perhaps the pink top is a bit too bold for my skin. I will study the color wheel more and do what I can to put what I learn into practice.

I thought the pink really stood out sharply as well. Perhaps a different shade of pink could be helpful. Salmon, or try darker with a Rose of some sort.

I will take your suggestion into consideration as well. Thanks for the idea.

Oh, I see! Hmm! That's interesting too!

Jeff, if you do that, you'll have to report it on flatheelplace.org, not here! LOL Just kidding.

 

Nice outfits. I agree on getting a navy bag. A brown one would have been better suited to the second outfit maybe.

 

Steve

Brown, with blue? Hmm! Interesting. Anyhoo, I'll see about getting my hands on a navy bag this weekend. Buying women's clothes, shoes and accessories is considerable fun.

Nice doubleheader Jeff!  I have a hard time geting out once, let alone twice in a day.  I like the pink outfit you wore!  As much as anything we wear though, I think wearing pink takes "guts"!  Especially in such a neon version of the color like you wore.  But again, well done!

Thanks for the kind words. I used to think that wearing pink as a male was a non-starter, but I've come to think that it's really no big deal as it's a nice color to wear. By the by, I forgot to mention that I had seen a guy around my age wearing rose pink Bermuda shorts, so I'm not alone in my appreciation for that color. HA!

Nice outings!

 

I think my own observations on women's shoes are often tied to the weather, day of the week and location of the country. More casual and less coverage in warm weather and on weekends. Here in the PNW, you tend to see a lot more heels and ankle boots in the non-summer months. The flip flops and flats are out in full force in summer.

Yes, I would agree the weather plays a big part in terms of shoes women wear, especially on weekends when they're off from work and don't have to worry about dress codes, and I can understand that. While I do have flats, I refuse to even think about wearing flip-flops.

I have a few pink shirts, but I am in "denial" and call them "coral." ha ha    Wear them all the time and really like them…..  Sometimes even with heels….   sf

I have a coral tank top, but I like the pink top that I wore yesterday more.

Greetings, friends! It's been awhile, but it's time for the SUNDAY DOUBLEHEADER!!!

Jaunt #279, 8/9/2015 (morning):

While I enjoy being nice and lazy on a Sunday, today, I just had a mad desire to go out in a skirt this morning, and since it was time for my morning supermarket run, I decided to kill two birds with one stone, going out in a blue t-shirt, an Old Navy 19 inch khaki skirt, the Payless "Genevieve" cognac loafers and a brown handbag. It was a little past eight a.m. when I arrived at the supermarket, there was a goodly crowd in the store when I entered, but that was no big deal as I grabbed a cart and strolled in. I did get a couple of stares here and there, but nothing more than normal, as long as I was properly dressed for the time of day and the environment I was in, I had no reason to feel nervous or out of place, and I was neither. The only discomfort came in the frozen foods section and having to feel those chilly temps on my bare legs. BBRRRRRRRR! But hey, in a way, that felt good too, all part of the overall experience. After some thirty minutes, I had shopped, paid for my goods and left for home.

Jaunt #280, 8/9/2015 (afternoon):

This outing was precipitated by having bought a fourth pair of "O'Malley" platform wedge slides in navy/pink (they call the color 'multi') at a Payless store downtown the day before, they were on sale for $10 bucks, how could I resist such a deal. The reason for having bought the slides that particular color was because I felt they'd match better with my blue denim skirts than the black pair, and I was eager to test that theory as I went out late in the morning wearing a pink tank top, my Old Navy 17 inch denim skirt and a black handbag. And, as you can see in the pictures below, the navy/pink did indeed go well with the skirt I wore, however, I didn't have a navy handbag to go with the shoes, a problem I'll address at my earliest opportunity. Once again, wearing the O'Malley slides made for quite a treat as I've come to love wearing these shoes, and with plenty of summer left, I'll have plenty more opportunity to wear them.

I headed west into Springfield for a short outing to take care of a couple of errands, the first to Bed Bath & Beyond to stock up on towels and washcloths, I spent a good twenty minutes in the store and, as usual, no one gave me so much as the time of day as I made my purchase. From there, I stopped off at Best Buy for some regular ogling of all things electrical and electronic, but I did have something I was looking for, that being the movie Hitman (after the videogame) which I want to see before the reboot comes out in a couple of weeks. Next up was lunch at Arby's where I enjoyed their newest sandwich, the maple bacon BLT which I had with a small cup of lemonade, and that sandwich was awfully darn good! My last stop of the day was downtown and the main branch of the Post Office to buy a money order. My wait in line was just five minutes before I got to counter, bought my money order, fill it out and send it off.

As usual, it felt damn good to be out and about in a skirt, and, by acting like what I wore was no big deal, no one else made a big deal out of it either. I also made a personal observation about shoes, I'd say that ninety-five percent of the women, young and old I saw while out and about wore either flat sandals or the dreaded flip-flops, heels was far and few inbetween, if at all. I got that because women were in casual mode and chose to wear flats, but to me, the O'Malley slides were MY casual shoes, despite the four inch heels, they just feel low in stature to me, not to mention supremely comfortable and easy to wear, just like flats. Perhaps I might experiment with flat sandals, just for fun, but for now, I'll stick to the O'Malleys for my summertime casual shoes. More to come....

Hi Jeff, 

Interesting observation and question. I certainly feel empowered by getting past the first heeling days and now have more confidence to wear what interests me, and now hosiery under shorts, skirts and unikilts are happening too. I think once someone gets by those initial fears and sees yes you can wear non traditional items and be safe there is much to explore. It does make me look at more items and think...could that work for me?   Sky is the limit..

To answer your question directly, does wearing heels make skirt wearing a natural progression? I think it allows us to expand to whatever we feel is a traditional ladies wear item and be more accessible males to wear. I wore corsets for many years before heels, then hosiery, heels and now skirts. An individuals journey to freestyle wearing.

Well said, my friend. I appreciate your well thought out comments.