JeffB

From the "Great Minds Think Alike" department, I was planning to start a thread about age and freestyling, but mlroseplant beat me to it, however, I don't mind that at all.

Now, I'm 57 and like to think I have a great pair of legs, enabling me to work a miniskirt and a pair of spike heels (or thigh high boots) just as well as any woman, if not better, but, more often than not, I tend to dress my age, mainly because I enjoy looking classy and stylish, something that suits the mental image I have of myself. perhaps that might be seen as staid, boring even, but I happen to like that image, especially since I spend a goodly period of time on my outings in broad daylight, surrounded by multitudes of people, so my goal is to blend in with my surroundings, to that end, I seek to dress like a middle aged woman. But, that doesn't mean I don't like to spice things up from time to time, and that's when I break out the minis as I look good in skirts of ANY length, and those are fun. As for striving to maintain my youth, I don't think that's important to me because I think young, but remain grounded, and I find that to be a healthy balance. I accept my age and dress appropriately because that makes me look classy when out in public, and that means a great deal to me.

By the by, CAT, you look great! Bravo to you!

heelsrus2000: While I like to think I have nice legs, I've found it hard to resist the longer skirts I've been sporting of late because they look nice on me. No, it's not like I'm hiding anything, I just like that particular style at present. Perhaps I'm dressing my age, perhaps, I won't deny that, but it's nothing to be ashamed of either.

TBG: Now I'm curious. I wish I could've seen that picture. Meanwhile....

Jaunt #331, 9/4/2016: I felt a goodly amount of melancholy associated with yesterday's outing because this figures to be the last time I do a jaunt on Sunday for the rest of the year after the NFL season starts up next week, and being a football freak in general and a Philadelphia Eagles fanatic in particular, my Sundays will be spent on the sofa until around early February or so. But I digress, for today's final Sunday outing, I thought I'd dress up a bit a black crinkle blouse, a print skirt, a new Liz Claiborne crossbody bag and, for the third time in the last seven days, the Payless "Tawny" crossband slides. What can I say? I really dig these shoes because they look good on me and go great with my skirts, especially the longer ones I've been wearing of late, in fact, I recent ordered those shoes in their other two colors, cognac (sort of a brown) and white, though with Labor Day here, I might not be able to wear the white pair until next spring. Regarding the new bag, while I enjoy the visceral thrill of a purse on my shoulder, a crossbody bag is even more fun as it leaves both hands free, and since I see many girls and women using such bags, I had to have one as well, and I liked it.

I headed to the greater northeast and Parx Casino to spend a few coins waging battle with those ever insidious one cent slot machines. As usual, no one on the floor pays me any attention as they're indulged in gaming, for anyone who wants a good place to go heeling, casinos and slot parlors are the way to go. After a light lunch, I got down to business, spending well over an hour and a half on the gaming floor when I wasn't pausing to watch the Phillies game on a TV over the bar, I played something like half a dozen machines and finished with a modest $110.00 in winnings, not at all bad for the time I invested, and while you NEVER get rich playing slot machines because the house always wins out in the end (and there have been times I've left slots parlors empty handed), it was still good fun, and that's all I'm after on my infrequent trips there. Feeling relatively flush, I left and drove into center city, stopping near my favorite hangout, Rittenhouse Square Park, with the weather sunny and pleasant with a nice little breeze that fluttered my skirt (something I get a thrill from), I found a bench and kicked back to relax and read from my nook e-reader among a throng of people as the park is always packed on a Sunday afternoon, in fact, I even got in some entertainment as a wedding party set up shop some twenty feet away for picture taking, the park is a great place for that when the weather is nice and I've seen that before, but not that close.

Just as enjoyable was strolling up and down a crowded street and having no one give me so much as even a mild glance, I was just another pedestrian, nothing more, nothing less, and that's more than good enough for me because that's the way I want things when I'm out and about, to blend in with my surroundings and go about my business just like everybody else. Isn't that the goal for everyone here? More to come....

On 9/2/2016 at 6:41 AM, mlroseplant said:

I have been thinking about this a lot lately. Maybe it will be a future subject in my thread.

Nice look, Jeff!

Perhaps in mine as well. Thanks for the kind words.

15 hours ago, Thighbootguy said:

I have also seen many women walking in heels that should have stuck to flats, and I think your goal is properly set.  My praise was for women that, while wearing heels, "carry themselves with a flowing grace" (envision ballroom dancing).  Not too many women pull that off, and I suspect even fewer guys (but ballroom dancers do have partners, but only one is normally in heels).  I do get complements like "You walk in heels better than I do" so I'm not staggering around in heels but I am far from moving with flowing grace.  (I can't dance either. )

Yes, I've gotten that compliment from time to time as well. That always makes me feel good as that's validation of my hard work to make sure I look AND walk my best in heels.

On 9/1/2016 at 3:59 PM, swedeheeler said:

Ordered this today just to complement for the short ones I got. 

http://www.ebay.de/itm/181708372785

Not my cup of tea, but hey, to each their own. I hope you enjoy it.

Now that September has arrived, summer will be winding down and fall will be on the way, that will mean changing my attire for the upcoming season. Deciding just when to stop wearing white clothes and shoes after Labor Day has gone; breaking out my long sleeves tops and jackets; swapping out my light fabric skirts for heavier fabrics; switching my slides and sandals in favor of pumps and boots. For sure warm weather will be around for awhile, at least for most of this month, but, as temperatures gradually cool, it'll be important for me to be prepared in terms of clothing and footwear for the season to come. For sure I'll be observing women as to what they'll be wearing and jotting down ideas for what will work for me in terms of fall attire.

19 hours ago, Thighbootguy said:

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

 

I got enough sun over the summer as it is, thankyouverymuch. 

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

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

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

On 8/26/2016 at 9:49 AM, Thighbootguy said:

Beauty is in the eye of the beholder.  It really is a matter of how we see ourselves. Some folks (male and female) like their look when wearing a tailored three piece suit, some folks really like their look wearing jeans. Some folks like to project a masculine look and others like to project a more feminine look.  The look we project is generally a reflection of what is inside the clothing and I am thankful that I live in a place and time that lets me make that projection.

Well, I'm proud to say I enjoy presenting a purely feminine look when on my outings. When I look pretty, I feel pretty, and it's a wonderful experience, I wouldn't have it any other way.

22 hours ago, bootedbloo said:

hi all

Just ordered a pair of Arollo Boots. Model is 'Queen'. Can't wait to get them & wear them out! I'll post my pics when I receive them. 

Impressive to say the least! I hope you'll enjoy them.

16 hours ago, heelsrus2000 said:

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

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

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

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

14 minutes ago, Thighbootguy said:

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

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

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

I rarely wear anything higher than four inches as I do a lot of standing and walking while on my little adventures, and I value comfort over heel height.

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

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

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

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

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

23 hours ago, Thighbootguy said:

Well done young man, well done. 

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

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

On 8/26/2016 at 9:54 AM, Rockpup said:

He studied nuclear engineering at MIT amd is a nuclear policy analyst. His FB shows quite a few pics of him in heels, it is fairly obvious he just wears whatever he wants. Good to see others are out there 'just doing it'

http://sdgln.com/news/2016/06/07/sam-brinton-talks-about-wearing-heels-walt-disney-world-inspiring-young-gay-child

Pretty darn cool!

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

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

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

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

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

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

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

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

This past Saturday, I bought a cute Liz Claiborne top and skirt set, both in light gray from JCPenney, and when I tried it on back home with a pair of black patent pumps (the Payless "Karmen" shoes), I was suitably impressed with how nice I looked, and that brought to light yet another paradigm shift in my ongoing evolution as a fashion freestyler: I look better as a guy in women's clothes than I do in men's clothes. I've made no secret of the fact that I can work a short, tight skirt and a pair of stiletto heels just as effectively as any woman, in some cases, better, and I'm proud of that admission. Few things in life makes me happier than when I'm strutting my stuff in a skirt or dress because I love wearing them, and, more importantly, I look damn good in them. I can only assume that I'm fortunate to be thin in stature, and my height also lends an air of style to the clothes I wear, plus the fact I go above and beyond to look nothing short than my very best when out and about, and that means everything to me. I've come to realize how women's clothes suits me in ways men's clothes don't, that I look better in a skirt of any length, color, fabric and style than dull and boring men's pants, and that knowledge is certainly intoxicating in ways I can't describe. I plan to continue strutting my stuff and looking my best in the clothes I choose to wear, and love to wear.

19 hours ago, Rockpup said:

Mom and gay son spots a guy wearing heels at Disney, mom tracks guy down to share this moment.

 

I found that to have been absolutely remarkable.

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

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

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

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

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

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

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

15 hours ago, Thighbootguy said:

But then there is the "Hurtles of high heels" that we all encounter.

I think we could have our own HHPLACE event.  We could award points for style, degree of difficulty (based on heel height), and inversely for speed (more point the longer your in heels).  There would also be additional points for venue: zero for staying at home, -1 for going out on a dark street at night, a bunch for going to a mall, a bigger bunch for wandering around downtown as @JeffB and @CAT do  , and a huge bunch for going to a motorcycle rally like @mlroseplantdid.

Heh! Sounds intriguing!

Very cool shoes, guys! I'm most impressed!

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

JeffB;

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

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

Thanks for the kind words!