SkirtDude Posted May 28, 2017 Posted May 28, 2017 (edited) 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 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! Edited June 10, 2017 by SkirtDude 1
Cali Posted May 28, 2017 Posted May 28, 2017 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 2
JeffB Posted May 29, 2017 Author Posted May 29, 2017 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.... 2 I don't want to LOOK like a woman, I just want to DRESS like a woman!
Thighbootguy Posted May 29, 2017 Posted May 29, 2017 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. 2 I dream of a world where chickens can cross roads without having their motives questioned.
JeffB Posted May 30, 2017 Author Posted May 30, 2017 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. 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! 1 I don't want to LOOK like a woman, I just want to DRESS like a woman!
mlroseplant Posted May 30, 2017 Posted May 30, 2017 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. 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! 2
SkirtDude Posted May 30, 2017 Posted May 30, 2017 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 Looking forward to your next jaunt 2
jeremy1986 Posted June 1, 2017 Posted June 1, 2017 On 29/05/2017 at 0:36 PM, JeffB said: 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!) 1
JeffB Posted June 2, 2017 Author Posted June 2, 2017 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. 1 I don't want to LOOK like a woman, I just want to DRESS like a woman!
JeffB Posted June 4, 2017 Author Posted June 4, 2017 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.... 1 I don't want to LOOK like a woman, I just want to DRESS like a woman!
SkirtDude Posted June 4, 2017 Posted June 4, 2017 (edited) Great look! Chino skirts are great, a good stepping stone to formal pencil skirts Those really do look like rose-tinted spectacles, as I can see a hint of pink reflecting off your glasses 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 I think the look would suit you... Edited June 4, 2017 by SkirtDude 1
JeffB Posted June 8, 2017 Author Posted June 8, 2017 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. 1 I don't want to LOOK like a woman, I just want to DRESS like a woman!
SkirtDude Posted June 10, 2017 Posted June 10, 2017 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? ) 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 1
JeffB Posted June 11, 2017 Author Posted June 11, 2017 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! 1 I don't want to LOOK like a woman, I just want to DRESS like a woman!
jeremy1986 Posted June 11, 2017 Posted June 11, 2017 20 minutes ago, JeffB said: You look great, @JeffB forgive me asking... but what kind of underwear do you wear on your jaunts? 1
Thighbootguy Posted June 11, 2017 Posted June 11, 2017 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. 1 I dream of a world where chickens can cross roads without having their motives questioned.
Thighbootguy Posted June 11, 2017 Posted June 11, 2017 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. Great outfit. The necklace, bracelet, and watch all work together to complete the look. To really finish things off add some small earrings (or great hooped ones) and more feminine glassed frames. 1 I dream of a world where chickens can cross roads without having their motives questioned.
JeffB Posted June 11, 2017 Author Posted June 11, 2017 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. Great outfit. The necklace, bracelet, and watch all work together to complete the look. To really finish things off add some small earrings (or great hooped ones) and more feminine glassed frames. 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!
KneeBooted Posted June 11, 2017 Posted June 11, 2017 @JeffB I thought I would let you know that you're semi-famous! I googled 'men in skirts and heels' earlier and look who showed up! 3
JeffB Posted June 12, 2017 Author Posted June 12, 2017 WOW! That takes me back! Seriously cool! Guess I got my fifteen minutes! I don't want to LOOK like a woman, I just want to DRESS like a woman!
Bubba136 Posted June 12, 2017 Posted June 12, 2017 I remember that picture! Being mentally comfortable in your own mind is the key to wearing heels in public.
nzfreestyler Posted June 12, 2017 Posted June 12, 2017 Hi Jeff, OMG. What a polished look ! I'm new here and I'm going to have to go back through this massive thread now to check out the style! 1
JeffB Posted June 12, 2017 Author Posted June 12, 2017 1 hour ago, nzfreestyler said: Hi Jeff, OMG. What a polished look ! I'm new here and I'm going to have to go back through this massive thread now to check out the style! Hello to you, nzfreestyler! Thanks for the kind words. I hope you enjoy my thread. And now....THE NUMBERS! JAUNTS BY YEAR 2008: 10 2009: 42 2010: 28 2011: 61 2012: 34 2013: 33 2014: 45 2015: 46 2016: 53 2017: 23 (and counting) CLOTHING Skirts: 290 (above knee-183, below knee-74, at knee-33) Jeans: 63 (tucked in boots-39, untucked-24) Skorts: 9 Dresses: 7 Capris: 4 Pants: 1 Long Sweaters: 1 FOOTWEAR Payless shoes: 235 Other shoes: 140 Boots: 135 (knee high-72, thigh high-45, ankle high-18) Pumps: 101 Sandals: 42 Loafers: 41 Slides: 31 Flats: 25 PERCENTAGES Skirts: 77.6 Jeans: 16.8 Skorts: 2.4 Dresses: 1.8 Capris: 1.0 Pants: 0.2 Long Sweaters: 0.2 Boots: 36.0 Pumps: 26.9 Sandals: 11.3 Loafers: 10.9 Slides: 8.3 Flats: 6.6 First skirt outing: 12/13/2008 First dress outing: 6/5/2011 Last outing in pants/jeans: 4/28/2013 1 I don't want to LOOK like a woman, I just want to DRESS like a woman!
nzfreestyler Posted June 12, 2017 Posted June 12, 2017 Hey thanks Do you employ a full time statistician! I might be available! Just kidding! Well I hadn't had a chance to look yet, but I definitely will. You have a lot of skirts, which is similar to myself, and I also see a lot above the knee. I too wear a lot above the knee, so I'll be going through this massive lot!!!! Ha - might have to call in sick tomorrow - it could take all day. 1
Thighbootguy Posted June 12, 2017 Posted June 12, 2017 (edited) @JeffB, based on your "NUMBERS" going back to 2011I have noticed a disturbing trend. It seems that you wearing of thigh boots has leveled off since July 2015 at 45 jaunts. Its been a while. Edited June 12, 2017 by Thighbootguy 1 I dream of a world where chickens can cross roads without having their motives questioned.
Cali Posted June 12, 2017 Posted June 12, 2017 (edited) While lately your Ankle High boots have skyrocketed. Me thinks some people have a lot of free time. Where are the flats and other footwear? Next I want a skirt/ dress broken down by height, and a pie chart on blouse color. No slacking off here. Edited June 12, 2017 by Cali 1
Thighbootguy Posted June 12, 2017 Posted June 12, 2017 (edited) 25 minutes ago, Cali said: Next I want a skirt/ dress broken down by height, and a pie chart on blouse color. No slacking off here. Admittedly this is selective reporting. As a former Data Base Administrator I generally didn't care what was in the database, rather, only that it was available for the user community so for those interested in further analysis , look at the posts in this list: 6-Jun-17 24-Dec-16 8-Aug-16 18-Jan-16 13-Jul-15 24-Dec-14 1-Oct-13 18-Sep-11 4-Mar-11 6-Jun-11 25 minutes ago, Cali said: Me thinks some people have a lot of free time. Yep... retired DBA. Edited June 12, 2017 by Thighbootguy Added links 1 I dream of a world where chickens can cross roads without having their motives questioned.
JeffB Posted June 13, 2017 Author Posted June 13, 2017 WOW! Graphs! Color me impressed! I'll have to see about upping the ante on the thigh boots! I don't want to LOOK like a woman, I just want to DRESS like a woman!
Thighbootguy Posted June 13, 2017 Posted June 13, 2017 4 hours ago, JeffB said: I'll have to see about upping the ante on the thigh boots! As I suspected, charts and graphs are the way into a statistician's heart. 1 I dream of a world where chickens can cross roads without having their motives questioned.
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