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The Jaunts of JeffB!


JeffB

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15 hours ago, JeffB said:

Now, why am I mentioning the gym so much? Well, since I was dissatisfied with a middle aged paunch I had developed, something that made fitting into some of my skirts a wee bit problematic, even with a body briefer I wear under my clothes, I decided it was time to exercise, eat healthy and trim down so I'll look better in my women's wear. I've been at it for two weeks now and lost a tad under ten pounds, and I already look better. I look forward to continuing my workout routine which I happen to enjoy and hope to slim down further. More to come....

 

You go girl :cheeky:
You'll look great and feel great!

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18 hours ago, Thighbootguy said:

I am somewhat surprised at my reaction when I scroll down in your post and see the pictures of a guy in a skirt or a dress.  For many months now the reaction has been "looks good".  I really don't see anything odd or unusual, rather a natural expression of fashion.  It has taken me a while to get to this point.  Thanks for bringing me (and all of us) along on the journey.

Repeating myself, the outfit looks good and very casual, but I still think some clip on earrings would be a nice accessory (as well as a pair of boots :penitent:).

:wavey:

Well, I'm glad to have changed your way of thinking. All I want to do is present the best public image possible, to prove that men can indeed wear women's clothing AS MEN and not look foolish or perverted. That's what fashion freestyling is all about, and I take what I do very seriously. Thanks for coming along for the ride.

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I don't want to LOOK like a woman, I just want to DRESS like a woman!

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While I don't wear skirts and dresses, I  wear many women's fashions daliy as a man. I have many women's tops and even a Victoria's Secret pull over sweater. It's amazing how many people compliment this sweater when I have it. Yesterday I wore a sleeveless turtleneck (VS) under a sweatshirt (jumper), jeans and my Charles By Charles David black laser cut wedges(tall wedges) to work.

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Jaunt #371, 5/20/2017: After some five straight days with abundant sunshine and temps in the low 90's which made it feel more like mid July than mid May, a cold front knocked down those temps considerably as we only saw a high in the low 60's with a cool wind and cloudy skies. However that didn't stop me from going on an outing, sporting my black denim jacket over a red t-shirt, a denim button down skirt, the Payless "Geneva" loafers and a black satchel bag.

My destination for the day was the King of Prussia Mall where I haven't been for over a month, arriving a little after eleven thirty, I hopped out of my car and walked right in, easy as you please as I've become acclimated to wearing skirts in the largest mall on the east coast, once upon a time, I never would've done something like this, now, I can't imagine visiting the mall unless I'm garbed in women's clothing. After a casual stroll to the comic book shop to buy the week's newest offerings, it was off to the food court for lunch, indulging in a chicken salad sandwich and a bottle of water from Chick-Fil-A, following lunch, I swung by JCPenney which was in the midst of a store closing sale, I wandered the floor for a good twenty or so minutes, but didn't see anything I liked, so I left. After leaving a candy shop where I treated myself to some mini gummi bears, a black woman in her late twenties said she liked my necklace, and I thanked her. It's always nice to get compliments from women about my attire, one outing, it's my skirt, on another, my shoes or my bag, or, in this case, my jewelry, once again, I guess that means I'm doing something right.

I wound up spending some three hours at the mall with nary an odd stare or glance from the scores of shoppers I passed in my travels. I guess I've gotten used to that, so I might push the envelope just a little bit on a future outing. We'll see. More to come....

Jaunt #371, outfit-1.jpg

Jaunt #371, outfit-2.jpg

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2 hours ago, jeremy1986 said:

Push it how, Jeff?

Oh, a shorter skirt, perhaps something just a little above the knee. No miniskirt, at least not right now, if at all.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Hate to say this, Jeff, but we're going to have to change your name to FlatsJeff....lol

Your outfits always look well put together.  Wear and enjoy!

 

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jeremy1986: Thanks for the kind words!

RonC: What can I say? There's a certain....something about flats that I like more than heels. Heh!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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Jaunt #372, 5/27/2017: Originally, I didn't think I'd get to go on an outing as the weather in these parts had been unstable over the last several days with rain, and today was supposed to have seen more of the same, but that never happened, as the sun came out with temps around 70, so I decided to head out in a black blouse, an olive crepe skirt, the Payless "Sinclair" platform wedge sandals in black and a black handbag. This is just the sort of casually dressy outfit I've come to enjoy wearing, and what I feel good wearing because it suits my particular style as a fashion freestyler. As I've said in this thread many, many times before, if you're going to wear women's clothes and shoes in public as a man, then you DAMN well better look good!

My first stop of the day was to a downtown branch of my bank to take care of a little business prior to the day's pleasure, and I was treated with all the respect of a customer seeking services, and my attire was never a concern, and I appreciated that. From there, it was off to downtown for a stop to my friendly neighborhood comic book shop where we got into a lively discussion about how miserable the hometown baseball team, the Phillies had stunk up the joint of late. Them it was off to Rittenhouse Square Park for a little relaxation time, for a late Saturday morning, there was a predictably large crowd enjoying the pleasant weather as I found a bench and sat down to chill. It was some twenty minutes later that a white haired gentleman who looked to be well in his 60's walked up to me, smiled and said he admired my skirt and said I looked comfortable in it, he then added that he used to wear a sarong and loved it. I smiled back and thanked him for the kind words before he left.

Now, it's exceedingly rare when I get compliments on my attire from men, so this came as quite the pleasant surprise, though one I appreciated as my prep time putting together my outfits yielded positive results. Thirty minutes later, I was back in my car and crushing over into South Jersey, namely Moorestown Mall and the multiplex where I saw Guardians of the Galaxy vol. 2 in a fairly packed theater, a wild and crazy summer popcorn flick that was great fun to watch. Afterwards, I wandered into the mall itself and ventured to Sears where I bought a couple of blouses, from one of which I look forward to wearing soon. Still, the highlight of my day was the compliment I got from that older gentleman, something that helps boost my confidence and validates how well I present myself to the world at large. More to come....

Jaunt #372, outfit-1.jpg

Jaunt #372, outfit-2.jpg

IMG_0412.JPG

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Great outfit.  Well done. 

Add small dark earrings with that necklace and those shades, it will add balance to the look.  Guys have been wearing earrings for a long time. Rather than assailing you with images, Google "guy wearing earrings image"

:wavey:

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Great Jaunt, Jeff! A skirt like the lady in the background would do you well, as they are more youthful. I see you pushed the envelope with a picture outside. Ask the next person who takes your pic to get a whole shot, including your shoes and the rest of your ensemble :cheeky: And as TBG says, earrings will complete the look, there are even clip-on ones if you don't wish to pierce your ears. Well done! :wave:

Edited by SkirtDude
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6 hours ago, JeffB said:

As I've said in this thread many, many times before, if you're going to wear women's clothes and shoes in public as a man, then you DAMN well better look good!

Very wise words. That's why I wear good looking heels at all times

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TBG: Admittedly, I'm not sold on earrings, but I'll keep an open mind about it. That certainly would be interesting though.

SkirtDude: Didn't even notice who was in the background when I took that picture. As for asking complete strangers to take my picture, hmm, not something I've ever considered, but I'll think about it for a future outing.

Jaunt #373, 5/28/2017: When I woke up in the morning, the first thought that popped into my mind was this: "I wonder if the weather will be good for an outing?" As it turned out the answer was "yes" as the forecast that called for some sun, some clouds and temps in the low 70's, so I thought I'd go casual with a turquoise tank top with a lace trimmed neckline, a denim miniskirt, and because it's Memorial Day weekend, I figured it was a good time to break out my white shoes, namely the Payless "Noble" flat sandals and a matching handbag. While I try to vary my hemlines from outing to outing to keep things interestinng, wearing a mini is lots of fun, mainly because I get to show off my legs, meanwhile, I've come to find wearing flat shoes to be just as much fun as heels, and sandals of any heel height are a blast.

I left a little before noon, heading west into Springfield where I stopped at Arby's for lunch, a roast beef sandwich and a bottle of water, then down to Best Buy for some ogling of gadgets and such before leaving with a Blu-Ray copy of The Great Wall which I had seen back in February and liked, so I was eager to add it to my home video library. And because I had nothing else better to do, other than go home and watch the Phillies lose again (they did), I headed into downtown to kill some time in my regular haunt of Rittenhouse Square Park with my nook e-reader while people came and went without giving me so much as a glance, with the exception of an old lady who stopped to say she liked my necklace and my top, remarking on how blue they both looked. I smiled and thanked her before she went on her way, now it's rare to get compliments as passersby don't give me so much as the time of day, but I got some kind words two outings in a row. Not bad, not bad at all.

I continue to be mildly amazed at how easy it is for me to come and go in public in women's wear, even a miniskirt, however, I don't take any success I have for granted, I continue to obsess over the image I present to the outside world, going out of my way to avoid looking silly, clownish or inappropriate, my goal is not to stand out (which can be hard to do in high heels because I'm already tall), but to blend in with my surroundings, to be just another pedestrian taking care of business or simply having a good time. More to come....

Jaunt #373, outfit-1.jpg

Jaunt #373, outfit-2.jpg

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4 hours ago, JeffB said:

my goal is not to stand out (which can be hard to do in high heels because I'm already tall), but to blend in with my surroundings

That's asking a lot in a turquoise top and a mini skirt, but well done just the same.  

When I compare the pictures in your most recent post with the ones in your immediately prior post I see an age difference (just based on the clothes) of at least 30 years.  I struggle with my selecting clothing that is for a person much younger than my chronological age, but then you are only as old as you feel, and I couldn't wear this stuff back then. :penitent:

:wavey: 

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18 hours ago, Thighbootguy said:

That's asking a lot in a turquoise top and a mini skirt, but well done just the same.  

When I compare the pictures in your most recent post with the ones in your immediately prior post I see an age difference (just based on the clothes) of at least 30 years.  I struggle with my selecting clothing that is for a person much younger than my chronological age, but then you are only as old as you feel, and I couldn't wear this stuff back then. :penitent:

:wavey: 

Hmm! It never occurred to me that a change in clothes could span such an age difference, but yeah, I can see what you're getting at, from Saturday's more staid ensemble to Sunday's more, well, risque outfit. Most interesting indeed!

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20 hours ago, Thighbootguy said:

That's asking a lot in a turquoise top and a mini skirt, but well done just the same.  

When I compare the pictures in your most recent post with the ones in your immediately prior post I see an age difference (just based on the clothes) of at least 30 years.  I struggle with my selecting clothing that is for a person much younger than my chronological age, but then you are only as old as you feel, and I couldn't wear this stuff back then. :penitent:

:wavey: 

That kind of hits home, as I struggle with the same issues myself.

Last fall, when our church was still searching for a new choir director, the church hired this young gal just graduated from college to fill in as choir director during the search for a permanent person. At the first rehearsal in September, she had each of us choir members introduce ourselves, and had us answer two questions: 1) What is your greatest weakness, and 2), What is something you've done in the past that you'll never do again?

The usual answers were something like what you'd expect, for example, chocolate and skydiving. When it came to my turn, I answered, "Wearing age inappropriate clothing, and once I tried wearing flats," as I sat there wearing tiny shorts, a tight t-shirt, and high heels. It was good for an actual, genuine laugh, anyway. These people know me, so it was not a nervous laugh. 

My reasoning, and I've discussed this productively with my wife, is that I like to see women dressed in this way, why wouldn't I try to emulate that style? I've still got the body for it (Well, almost. I'm still chasing that perfectly flat stomach, but I'm close), so why not?

My question to you, @JeffB is, do you use the same process when you put together your outfits, in other words, do you sort of copy an outfit that you like that you've seen on somebody else, and if so, are the women that you copy of a certain age range? Or do you just dream up an outfit from your head? You always do such a nice job of looking put together in a way that I often do not. Thanks in advance!

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8 hours ago, JeffB said:

Hmm! It never occurred to me that a change in clothes could span such an age difference, but yeah, I can see what you're getting at, from Saturday's more staid ensemble to Sunday's more, well, risque outfit. Most interesting indeed!

I prefer Sunday's look to Saturday's, as it's taken 20 years off you! You've got the figure for the shorter tighter stuff and I think you shouldn't hide it away in unflattering crepe skirts but that's just my opinion. I wear denim pencil skirts just above my knee (23 inch), enough to be smart, yet if it's a nice fitted designer like D&G with a generous slit at the back, it's kind of sassy which makes me feel good. Shorter skirts are nice but I'm just worried with modesty, but you can pull off that look! I was wondering the same about your combinations, whatever it is you do it looks great :cheeky: 

Looking forward to your next jaunt :)

 

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On ‎29‎/‎05‎/‎2017 at 0:36 PM, JeffB said:

Jaunt #373, outfit-2.jpg

Love this look!

Denim mini's (or most denim skirts in general) always make me miss a heart beat ... and those flat are perfect with it! 

I agree  - I have also learnt (via my wife) that flats can also be sexy too (though I will always choose heels first!)

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On 5/30/2017 at 7:14 AM, mlroseplant said:

My question to you, @JeffB is, do you use the same process when you put together your outfits, in other words, do you sort of copy an outfit that you like that you've seen on somebody else, and if so, are the women that you copy of a certain age range? Or do you just dream up an outfit from your head? You always do such a nice job of looking put together in a way that I often do not. Thanks in advance!

Well, when it comes to putting together outfits, I usually subscribe to the Indiana Jones Method, in other words, I make things up as I go along. Sometimes, I emulate outfits I see women wear, other times, I come up with my own ideas and inspirations based on several factors: 1) the time of year; 2) the weather; 3) the surroundings I plan to be in; 4) my mood. But, I don't do much copying as I prefer to work from my imagination and create my own outfits, and since I have a fairly large selection of clothing and footwear to draw upon, the combinations I can create are considerable. And I do a great deal of experimenting when it comes to creating outfits, it's not uncommon for me to spend at least an hour fiddling around with tops and skirts until I assemble something I like and feel good wearing in public because I never leave the house unless I'm one hundred percent satisfied with how I look. I hope this was of help.

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Jaunt #374, 6/3/2017: With a new month having begun, Saturday started with some showers and a chilly wind, by the time ten a.m. rolled around, it was still cloudy and a tad nippy, so I dressed for the occasion, sporting my denim jacket over a pink t-shirt, a 22 inch black chino skirt, the Payless "Geneva" loafers and a black satchel bag for an outing to the King of Prussia Mall. After a stop to a gas station to fuel up, I drove straight to the mall, my goal on this, my seventh jaunt to KOP was to push the envelope, even if just a little, going from those just below the knee button down skirts to what I wore today which was above the knee by some three to four inches. After arriving at KOP shortly after 11, I hopped out of the car and strolled into the mall, wondering if anyone would notice either the pink shirt or the shorter skirt.

As usual, the answer to that was a big, fat nope. Big surprise, eh? Nary any widened eyes, gasps, double takes, long stares, none of it, but, I've gotten used to that. The more important thing was that it felt extremely good to come and go as I pleased, dressed the way I wanted, in the largest mall on the east coast, and that's plenty awesome, and that made the outing all the more enjoyable. From having lunch in the crowded food court to some shopping at JCPenney which is slated to close, enabling me to catch a good deal on a couple of dressy skirts I bought for just under twenty-three bucks, not too bad, I'll have to go back to see what else I can get my hands on before the store closes. I wound up spending about four hours at the mall, it's amazing how time flies when you're having fun, and I certainly did enjoy my time there, in fact, it's pretty much become a given that I'll only go to KOP in a skirt because I've become acclimated to it, and I like that.

Perhaps I'll push the envelope a little more on my next trip there with a shorter hemline, or maybe with one of my form hugging pencil skirts, and since it's spring, with summer right around the corner, why not wear a pair of sandals. We'll see. More to come....

Jaunt #374, outfit-1.jpg

Jaunt #374, outfit-2.jpg

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Great look! Chino skirts are great, a good stepping stone to formal pencil skirts :silly: Those really do look like rose-tinted spectacles, as I can see a hint of pink reflecting off your glasses :lol: The length is great, I wouldn't wear anything too short but a tighter pencil skirt would look great on you. Why not try a formal cotton pencil skirt such as what most wear to work rather than chino or denim? There are some nice ones about, in gray / black / navy or other colours that can still look casual for a jaunt, or can be dressed up for work etc (see attached) and the shoes are cute too. That's an image from La Redoute UK (posed by model), though I'm sure the likes of Sears would have these commonplace skirts for sale. I generally go for 24 inch, sometimes 27 which I think can still look great. Less is more, a longer skirt looks good rather than one halfway up your thigh... I also stand with my legs closer together as well. I'm still a guy but that's how I'd stand in a skirt :cheeky:

I think the look would suit you... :)

 

 

smart_black.PNG

Edited by SkirtDude
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SkirtDude: Regarding that picture, one of the skirts I bought last Saturday looked like the one you displayed, I just need a dressy looking blouse to pair with it and I'll have a great looking outfit. I take wearing women's clothes seriously and want to look my best in them. By the by, thanks for the suggestions.

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On Thursday, June 08, 2017 at 10:44 PM, JeffB said:

SkirtDude: Regarding that picture, one of the skirts I bought last Saturday looked like the one you displayed, I just need a dressy looking blouse to pair with it and I'll have a great looking outfit. I take wearing women's clothes seriously and want to look my best in them. By the by, thanks for the suggestions.

I know the effort you go to, and I am sure it will look fabulous! I have been wearing formal pencils for years, and have had nothing but compliments. Denim ones are great for casual trips, like chino ones, but the formal skirt is very versatile, it would look good with loads of existing tops in your vast collection! I am an avid follower of your thread (who would have guessed? :silly: ) and since quitting the other forum due to racist comments I have been keeping a low profile in general. But seeing what sartorial rabbit you will next pull out of the hat has given me confidence and ideas for my wardrobe too. I have also added back in regular guy stuff as I need balance as well.  A skirt suit would suit you as well, but I am keen to see your formal skirt, even a simple white blouse would look good with it. Team it with stockings (too hot for tights) and pumps! 

Looking forward to your next jaunt :) 

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Jaunt #375, 6/10/2017: Gotta love a warm and sunny day since that gives me all the impetus I need to go on an outing, garbed in a turquoise blouse, a dark gray denim pencil skirt, the Payless "Stacia" low wedge sandals in black and a black handbag. I would call this outfit casually dressy as in the blouse being dressy and the skirt as casual, and it makes for a nice combination along with the comfortable sandals for the amount of time I'd be on my feet. My first stop was to the main branch of the Post Office to buy a money order, walking in, there was a crazy long line in another area of the main floor for people waiting to have passport pictures taken, I did get a couple of stares here and there, meanwhile, my time spent in the main line was only a tad over five minutes before I made it to the counter to buy my money order, fill it out, slap it in a envelope and leave.

My next stop was to the Rittenhouse Square Park area to chill for a bit, for me, it's not just sitting on a bench in the park so I could be seen and go ignored, I just enjoy the ambience of the park, the combination of shade, warm weather and the throngs of people who came and went, the park is just a great place to be, whether to read, check stuff on social media or just relax. It's fun! Now, here's something that will make Thighbootguy in particular chuckle since he's said more than once that I'm able to come and go as I please because people identify me as female, as I entered Barnes & Noble after about an hour in the park, the security guard at the door, a thirtysomething black woman said, "Good afternoon, Miss." That made me chuckle as I replied to her. After buying the newest Sports Illustrated, I left and walked down a mondo crowded street some two blocks to the Apple Store where I bought an armband for my iPhone to use while working out at the gym.

Returning to the car, I drove over the bridge to South Jersey and the Moorestown Mall area where I had lunch at Wendy's, a Caesar salad and a bottle of water, then to the nearby multiplex to watch Wonder Woman which was flat out awesome. And while I probably enough in the way of women's clothes, I went to Sears and added another couple of blouses and another crinkle skirt like many of the others I already have, followed by some wandering through the Moorestown Mall itself which didn't have quite a large crowd like say, King of Prussia, still, it was plenty of fun. My outing lasted close to seven hours and I enjoyed every minute. More to come, including....THE NUMBERS!

Jaunt #375, outfit-1.jpg

Jaunt #375, outfit-2.jpg

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2 hours ago, jeremy1986 said:

You look great, @JeffB

forgive me asking... but what kind of underwear do you wear on your jaunts?

In years past, the answer to this question brought an admonishment from the Admins that it was  "Way too much information".  I suggest this be continued as a PM.

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3 hours ago, JeffB said:

as I entered Barnes & Noble after about an hour in the park, the security guard at the door, a thirtysomething black woman said, "Good afternoon, Miss."

Glad to know I'm not alone in my assessment. :penitent:

Great outfit.  The necklace, bracelet, and watch all work together to complete the look.:thumbsup: To really finish things off add some small earrings (or great hooped ones) and more feminine glassed frames.

:wavey:

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6 hours ago, Thighbootguy said:

In years past, the answer to this question brought an admonishment from the Admins that it was  "Way too much information".  I suggest this be continued as a PM.

Quite right. However, I will provide an answer to jeremy, that being....black. And that's as far as I'll go on that subject.

6 hours ago, Thighbootguy said:

Glad to know I'm not alone in my assessment. :penitent:

Great outfit.  The necklace, bracelet, and watch all work together to complete the look.:thumbsup: To really finish things off add some small earrings (or great hooped ones) and more feminine glassed frames.

:wavey:

In retrospect, I find myself being amused at having been called "Miss". A first for me to say the least. Heh!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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