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The Jaunts of JeffB!


JeffB

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Well done JeffB. Another nice looking outfit. I like the color combination ! But what a surprise to see you are not wearing heels ? Lucky for you the temperature was warm enough to wear a skirt. I woke up this morning and looked outside to see a trace of snow my neighbor's car...

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Bluejay: Thanks for the kind words. Wearing skirts is great fun and I do all I can to look my very best in them. TBG: What happened on Saturday proved to me how I never know what to expect when I go on one of my little expeditions. It was refreshing to have encountered those girls who were both openminded and complimentary as well. Danielp6406: Thanks for the compliment. As for wearing skirts, temperature doesn't matter to me, I've worn them when it was 20 degrees and when it was 90 in the shade. It's just a matter of what I wear with them. Heh! Regarding heels, they're just part of what I wear with my outfits, not the be all and end all when I go on my outings.

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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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Good to see your Jaunts again, Jeff! I was getting worried. You've got great legs for those skirts, I'm so jealous :mecry: The weather in the UK is too cold for short skirts, even in a pencil skirt I'm still cold :smile: Looking forward to your next jaunt :unsure:

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Kilty: Thanks for the kind words. I'm lucky that I do manage to look good in a skirt, especially a short skirt, and I like to express how much fun it is to wear them in public. And the jaunts will keep on coming! canadianbeaver17: Indeed! I'm still rather surprised to have been complimented bythat particular demographic.

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

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I'm trying to get out there more, I've got a cute denim skirt I wear, it's been so cold I bought myself some slips to wear under it :unsure: Still looking for some decent shoes for my outfit, my mrs has some old boots, with quite a chunky heel I might get, or just pick up a pair in a thrift store. looking forward to your next jaunt :mecry:

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  • 2 weeks later...

Jaunt #148, 5/12/2012:

After what seemed like an eternity, sunshine and blue skies and warm temps returned to my neck of the woods the other day, and with conditions remaining the same today, I hit the road for a new outing. And because the weather was so gosh darn wonderful, I went out in a skirt, my familiar 22 inch denim skirt that I've had for almost four years now which I paired with a blue campshirt, the two inch heeled Blondo loafers and my trust Buxton Bag. I've said this before (and if you find this boring, forgive me), but I've become really comfortable and at ease wearing skirts on my outings, moreso at times than in heels, and that comfort shows in my deportment while out and about on my little expeditions.

Anyhoo, I headed into town to visit my favorite comic shop, this time, I managed to park literally across the street from the shop, so I went in, bought this week's new books and yakked some more about the live action Avengers film. After leaving the shop, I went around the corner to a nearby convienience store to buy a newspaper, but they were out, so I went to another store little over a block away, this afforded me an opportunity to be seen by passersby and folks dining outside eateries, but no one paid me any attention. I guess that a guy in a skirt is no big deal in downtown Philadelphia. And, by my attitude, calm and casual, like what I'm wearing is no big deal, I helped to reinforce that belief. And, as I stated in a previous post, wearing a short skirt in hot weather is a delightful experience because I'm left cool and comfortable because my legs aren't encased in stuffy material. I can't believe more guys haven't discovered or taken advantage of this wonderful pleasure!

From there, it was off to South Jersey and back to Chick-Fil-A for lunch. Even though the store was fairly crowded, no one gave me much if anything in the way of stares or double takes. Once I purchased my lunch, I sat down at a table, but I was right next to a young mother and three kids, none of whom looked to be any older than four or five. The kids did stare at me off and on (more on than off) while I ate, but I ignored them, and, much to my surprise, they didn't blab to high heaven about the guy in a skirt. I've had that happen a time or two and that's not exactly pleasant. That little brood left some ten minutes before I did, but the place had become even more crowded, but I walked right out the store, pretty as you please. My next stop was to Barnes & Noble where I spent well over half an hour in the lounge with a couple of magazines and a lemonade, sitting at a table, I crossed my legs like a woman so everyone could see me while I read and drank.

My next and final stop of the day was to the nearby Best Buy where I spent another half hour plus, wandering the aisles of goodies before leaving with Underworld: Evolution on Blu-Ray and a new pair of headphones as my old ones had given up the ghost. Once again, no one bothered me, no one stared or gawked, of course, someone might have snapped a pic on their camera equipped cellphone, but hey, that's the risk I take when I go out dressed the way I like. All in all, another good outing, and with warmer weather on the way, I foresee many more outings in skirts to come!

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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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I enjoy reading your stuff Jeff. Even if not much of anything happens. Nice outing.

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Shafted, the boots that is! View my gallery here http://www.hhplace.o...afteds-gallery/ or view my heeling thread here http://www.hhplace.org/topic/3850-new-pair-of-boots-starts-me-serious-street-heeling/ - Pm me if you want fashion advice or just need someone to talk to.

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I enjoy reading your stuff Jeff. Even if not much of anything happens. Nice outing.

Many thanks. Well, if nothing happened during my outing, then that meant I was doing things right, that I dressed appropriately for my surroundings, thus avoiding any sort of fuss. I want to show through my actions that men CAN look tasteful in skirts and not be seen as some sort of freak or oddity.

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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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JeffB.. I truly enjoy reading about your outings and I must admit, It has me stirring up the possibility that I might try doing a skirt sometime. I had surgery recently and cant wear pants. Well.. I can but the constriction of pants is causing flaring/swelling and more air circulation will help with the healing. Ive worn a few skirts around the house as of late and Darian bought me a Kilt. The comfort is a whole new story compared to regular pants. I just dont feel I could pull off a skirt. Heels/boots is one thing, but a skirt is another story ;) . Its not a confidence thing, but a ' I dont think I would look right ' or the whole ' self image ' of how I see myself dressed isnt there for it. -ILK.

REPEATEDLY ARGUMENTATIVE, INSULTING AND RUDE. BANNED FOR LIFE.

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JeffB..

I truly enjoy reading about your outings and I must admit, It has me stirring up the possibility that I might try doing a skirt sometime.

I had surgery recently and cant wear pants. Well.. I can but the constriction of pants is causing flaring/swelling and more air circulation will help with the healing. Ive worn a few skirts around the house as of late and Darian bought me a Kilt. The comfort is a whole new story compared to regular pants.

I just dont feel I could pull off a skirt. Heels/boots is one thing, but a skirt is another story ;) .

Its not a confidence thing, but a ' I dont think I would look right ' or the whole ' self image ' of how I see myself dressed isnt there for it.

-ILK.

How interesting. Well, you never know what you can do until you try and see what happens. When I first contemplated wearing a skirt way back in 2008, I also didn't think I'd look good or look right in one, but I decided to go ahead and give it a go anyway, and I've been having fun ever since. Don't let self-image issues stop you from wearing a skirt if that's what you want to do. Sure, it's bound to be a tad unnerving at first, because, unlike heels, there's NO hiding a skirt while out in public, but if you look stylish and tasteful for whatever surroundings you happen to travel in, I think you'll do well. Good luck!

Jaunt #149, 5/13/2012:

With another sunny and warm day on tap, and a couple of errands that needed my attention, I decided to turn this into a jaunt, and, like yesterday, I ached to show off my legs, and I did so in a 17 inch beige skort paired with a blue polo shirt, the Payless "Janis" low-heeled pumps and a handbag. I suppose this could be seen as another example of pushing the envelope as this had been the first time I wore a skirt or skort that was so bright in color, and this, I figured was bound to attract attention, that and the fact it was very short, showing off plenty of leg, but that prospect excited me very much. My first stop was to a local ATM machine in the Univiersity City area for some cash, hopping out, I did catch the eyes of a group of young Asians, two males and three females, and they did give me a long look as I walked past, but nothing more. Like yesterday, I felt cool and comfortable, and the skort felt so light and airy, it was almost like I wasn't wearing anything at all. Along with the loud, solid clack of the two inch heels on the pavement, it combined to make me feel good.

From there, it was off to the main branch of the city's Post Office which had limited Sunday hours, and I had to mail off a parcel and buy a money order. Upon arriving, I hopped right out without hesitation and walked in, the line inside was seven deep, but I didn't mind, if anything, this would afford me the opportunity to gauge reactions of those around me, but other than a lady ahed of me saying hello, there were no reactions, no wide-eyed stares of double takes at the sight of a guy in a short skort and heels and hefting a handbag. Just going about my business, I paid for the money order and the parcel I had to mail, simple as that, and no one paid me any mind, something I found a tad curious, but I accepted that. After leaving the post office, I headed west to Springfield where I stopped at Subway for lunch, there were only four people in the shop, three teenagers treating their mom to lunch, something I thought was plenty cool. I did get a stare and cocked eyebrow from one of the kids, a girl, but nothing more than that, they left while I was halfway through my lunch and had the place to myself.

My last stop of the day was to Bed Bath & Beyond as I needed some washcloths, the store was pretty crowded, and I did get some stares, however, that was all I got as I casually wandered the aisles until I found what I wanted, paid for same then left. Another good jaunt, and all the while, I felt comfortable and at ease (and delightfully cool) in my outfit, as I've said before, wearing skirts and skorts is as natural and commonplace to me these days as wearing pants is to everyone else, and I've embraced that comfort level, on top of that, any chance I can get to show off my killer legs is worth the opportunity! Meanwhile, my next jaunt, my 150th WILL be in a dress! Count on that!

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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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Thanks for the read JeffB! Your outings always seem so effortless and comfortable for you, it's a great attribute to have I think. Also congratulations on your next jaunt being your 150th documented!

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JeffB, You had two nice outings, this past weekend. Your outfits looked very nice. I especially liked the off white skort and royal blue shirt. That is also a favorite color combination of mine. I like to wear the royal blue shirts with white pants, cropped jeans and white capris but I still have to wait to after Memorial Day to wear white! (I might hear from some fashion fashinato that white slacks, capris or shorts are for the period between Memorial Day and Labor Day, Ha Ha.) Happy Heeling, bluejay

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Thanks for the kind words, guys! Much appreciated! By the by, bluejay, being something of a renegade, I decided not to wait for Memorial Day to wear a light colored item! HA!

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

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Jeff, The denim skirt you wore in your most recent jaunt looks gorgeous :yummy: I wish I had the confidence you do, I feel so exposed when I'm out and about, yet I read of you just getting out there and going about your everyday duties... :cool1: I still stand like a man alot in a skirt, so I'm trying to learn your demure poses, but want to be able to comport myself in such a way it doesn't look forced :cry1: Looking forward to your next jaunt - wish we had better weather here in London, it's not exactly skirt-friendly at the minute with all this rain and cold winds... :text_sigh:

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Jeff,

The denim skirt you wore in your most recent jaunt looks gorgeous :yummy: I wish I had the confidence you do, I feel so exposed when I'm out and about, yet I read of you just getting out there and going about your everyday duties... :cool1: I still stand like a man alot in a skirt, so I'm trying to learn your demure poses, but want to be able to comport myself in such a way it doesn't look forced :cry1:

Looking forward to your next jaunt - wish we had better weather here in London, it's not exactly skirt-friendly at the minute with all this rain and cold winds... :text_sigh:

Thank you for your kind words. I greatly appreciate them as I do my very best to look as stylish and tasteful as possible, and while I try to avoid tooting my own horn, I think I look damn good in a skirt, and that goes a long way towards the image I present while in public. Regarding the poses I display, it's all about practice, practice and still more practice (in private in front of a floor length mirror) so I don't affect the posture of, well, a man in a skirt, and I do all I can to walk, stand and even sit like a woman while out and about. It certainly takes a lot of work, but what I do can be done by others. I'm glad you enjoy my little adventures.

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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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Jaunt #150, 5/19/2012

As promised, I wore a dress for my 150th jaunt, but I did a little tweaking here and there for this special occasion yesterday. Normally, I rarely if ever go out at night since I'm not a night person and I'm usually in bed by ten or so, but for this jaunt, I decided to pull out the stops and look really fancy, and I did by donning my sleeveless black sheath dress which I first wore a year ago around this time on my 100th jaunt along with my black blazer, off-black pantyhose, the Pleaser "Vanity" 4 inch heeled pumps in black patent and two new items: a black faux croc print clutch bag and a strand of pearls, yes, pearls. Looking at myself in the mirror, I nodded from appreciation, having arrived at the conclusion that I've never better, and I certainly felt fabulous, also, this outfit perfectly put into perspective my new philosophy on freestyling: "I don't want to LOOK like a woman, I just want to DRESS like a woman".

Now, an outfit like this would've looked considerably out of place in broad daylight unless it was Sunday morning and I was headed to church (something I might consider in the future, I'm sure the Man upstairs doesn't care how his worshipers are dressed), so I decided to go out to dinner instead. With that in mind, I headed out to the western 'burbs and to Olive Garden, after arriving in the parking lot which was fairly full, I hopped out with no hesitation, feeling cool and calm and confident, I strolled to the restaurant, pretty as you please, thrilling to the clicking of my heels and how great it felt to be wearing a dress. When I entered, there were several patrons waiting to be seated, I got a couple of short stares and a cocked eyebrow, but nothing more than that. After a few minutes, a waitress gave me a smiled and took me into the dining area, the place was packed and I got a goodly number of stares, but I ignored them and strolled right past, feeling plenty bold and not caring about the reactions I got.

Admittedly, I did feel a wee bit self-conscious when I took off my blazer and displayed how broad shouldered I looked in the sleeveless dress, not to mention how snug it was, even though it was a size 16, the largest size available (If I'm going to continue wearing dresses, I might have to shop in the Plus size department in the future), but, all in all, no big deal. Even though the place was packed, no one gave me the time of day while I dined, enjoying chicken and shrimp carbonara which was fantastic while the person who waited on me was pleasant and professional from the word go, something I appreciated. As I finished, I got a pleasant surprise when a couple of black women around my age walked up to my table, one said I looked stylish while the other said she liked my pearls. With a smile, I thanked them both, adding that I didn't expect a compliment because of what I was wearing, the ladies pish-poshed and said they didn't care that I was a man in a dress, only that I dressed nice.

Pretty cool, eh? I certainly thought so. And, after paying my bill (giving my waitress a nice tip), I headed home on quite a high, thanks to those kind words I got. And with that, another push of my freestyling envelope was made as I dressed appropriately for a night out and had a great time, even if all I did was stuff my face. Heh! Bottom line, I felt comfortable and at ease, and that was the important thing, and it gave me courage to want to do something like this again in the future. More fun to come!

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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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Proof positive Jeff. If done right the sky's the limit. And people will have no problem with it.

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Shafted, the boots that is! View my gallery here http://www.hhplace.o...afteds-gallery/ or view my heeling thread here http://www.hhplace.org/topic/3850-new-pair-of-boots-starts-me-serious-street-heeling/ - Pm me if you want fashion advice or just need someone to talk to.

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Shafted: I couldn't agree more! Those compliments did indeed validate the appropriateness of my outfit last night.

skirtedvik: Good idea! I'll see if I can find one.

Jaunt #151, 5/20/2012

After dining out last night in a dress, I thought I head out into the sunshine for a new jaunt today. Even better, I pushed the envelope yet again buy wearing---get ready for it---FLATS!! Yes, boys and girls, no heels today, and that was very much intentional as I had been eager to get my hands on a pair of flat shoes for jaunting and I found a nice pair on the Payless website:

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Those are the "Cori" flats with a 1 1/2" wedge heel, when I saw those shoes last week, I just HAD to have them, so I ordered a pair and was lucky that they came in 13 wide, and they were stylish and comfortable, so I paired them up for today's outing with a denim campshirt, my Old Navy 17 inch denim skirt and my Buxton Bag. Showing off my legs has become somewhat commonplace for me of late, and with temps reaching into the high 70's, it was a good day to wear a short skirt which made me feel quite cool. I headed back out to the western 'burbs where I stopped first at Best Buy, hopped out and went right in, earning a couple of stares from shoppers who entered with me. I spent the next thirty plus minutes goofing off and wandering the aisles before going to the check out line with the Blu-Ray version of 2001: A Space Odyssey. Just like last week, I felt airy in that skirt which was fun to wear, especially with my new shoes.

From there, it was off to Subway for lunch, unlike last week, I had the place all to myself for the most part, and here's where some delicious irony comes in. While I ate, a woman who looked to be a tad older than me walked in, and damned if she wasn't wearing the very same shoes I was, only she had pants on. I don't think she noticed me, or the fact I had on the same shoes, and that made me chuckle. After I finished, I left and headed down the road to the strip mall where Borders bookstore used to be and went to Hallmark to buy a birthday card for a co-worker, there were several people in the store, but no one paid me any attention, a nice thing, and I can't emphasize this enough: as long as you dress appropriately for whatever surroundings you happen to be in, chances are excellent you will manage to blend in. And that's why I longed to wear flats because, as I've observed, not even women wear heels ALL the time.

I see this as yet another sign of my continuing evolution as a freestyler as I went out of my way NOT to wear heels on an outing, and I still had fun!

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Edited by JeffB

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

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JeffB- #150 was well done indeed! I was going to comment that I led the look with the blazer better than without bit I think skirtedvik has the right idea of a short jacket.

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I dream of a world where chickens can cross roads without having their motives questioned.

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JeffB, Great jaunts you had. You looked very stunning in your dress and heels. I also liked your flats you wore with your skirt. Flats do have a place in a wardrobe, as I have several pair of "Georgio Butini" men's designer shoes that look more like women's flats then men's shoes. Again Great looks! Happy Heeling, bluejay

Edited by bluejay
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TBG: Yes, I do plan to search for a short blazer this weekend. I'm sure I can make that sort of look work. On the subject of blazers, I've worn gray and now black, since I wouldn't want to repeat myself on a future jaunt in my dress, I wonder what color would work best with a black dress? Hmm! Bluejay: Thanks for your kind words. I certainly felt great inside the whole time I had the dress on, and it was wondrous. Something tells me I won't wait for my 200th jaunt before I go out again in a dress! By the by, I had fun wearing those flats on Sunday. I'll be getting lots of mileage out of them this coming summer! rxrenesis: Thanks! I try as best I can to inspire others.

Edited by JeffB

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

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Jeff,

New dress for your 200th Jaunt? :) Love the skirt in your most recent jaunt, I might get some flats soon :) Looking forward to your next instalment :)

Many thanks for the kind words! Most appreciated!

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

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Look especially sharp and stylish Jeff, a great way to celebrate your 150th jaunt. I really like the length of the blazer falling on the hip which is very flattering. For sure give a shorter jacket a try too (they never seem to work for me but my legs are probably half the length of yours!). As for colours I tend to find a darker jacket over a lighter coloured dress (or skirt and top) tends to rebalance the proportions of relatively narrow hips to wider shoulders. It's not that I wouldn't wear a lighter jacket over a darker dress, just that the cut of the outfit becomes a lot more important to making it work. I really admire that you seem to grow in confidence with summer outfits, that's very inspiring as I tend to feel more comfortable in winter.

If you like it, wear it.

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SleekHeels: Thanks for the suggestions. I found them useful and I'll try to utilize them. Wearing dresses and skirts is clearly a sign to me that it's no longer about just the shoes, rather, the entire outfit, and, at the risk of sounding vain, I love showing off my legs, something I can't do properly in jeans. Heh! As for confidence, as long as you have it, and flaunt it, it doesn't matter what the season might be, just go out there and do it!

Jaunt #152, 5/26/2012

Even though the forecast called for steamy, summer like temperatures, it would also be sunny, good enough conditions for a Saturday jaunt as I took my new Payless "Cori" flats for a second trip while wearing a blue campshirt, a new skirt I bought from Sears and a handbag. Given how most women dress down on weekends, I decided to follow their example, for the most part. Heh! I was especially eager to wear the new flats again as they were very comfortable, stylish and, yes, cute! And what self-respecting freestyler wouldn't want to wear cute shoes? As for the new skirt, it's a gauzy, black, 30 inch A-line with a matching half-slip like attachment beneath, and, like the shoes, it proved to be a lot of fun to wear. My first stop was to Starbucks to read a magazine, buy a cool beverage, and be seen. Even though there was quite a crowd in the place, no one paid me any attention as I got my order, sat in a chair and spent over thirty minutes there.

After that, it was off to center city and my favorite comic shop, as usual, finding a place to park proved time consuming and I wound up in a spot over a block away, no prob, again, it offered me a chance to be seen in my outfit, and, other than a trio of young black males who broke out laughing as they drove past, no one paid me any mind as I strolled to the shop, enjoying the soft swish of the skirt about my legs and the comfort of the shoes. I spent nearly half an hour in the comic shop, half that time yakking with the staff about The Avengers which I had seen last weekend and loved, as usual, they ignored what I wore. Then I left the store, walked up the block to a convenience store to play the lottery and buy a newspaper, then it was off to South Jersey. When I entered the Chick-Fil-A near Moorestown Mall, I did get some glances from a few people here and there, but nothing more than that, I bought my order, ate while gazing through the sports section and left, simple as that.

My last stop of the day was the nearby Barnes & Noble where I spent another half-hour plus in the dining area with a couple of magazines and a tall iced tea. Yes, I drank a lot, but it was hot, and it's important to stay hydrated. There wasn't much of a crowd in the store, and what people there were in attendance ignored me. Funny how a guy in a skirt didn't raise so much as one eyebrow. Nevertheless, I had another fun time freestyling, it felt great to wear that breezy, gauzy skirt, and those "Cori" flats were an absolute delight to wear because they were so comfortable! Who needs heels when I've got great flats like those! I can see I'll be getting a lot of use out of those shoes in the weeks to come!

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Edited by JeffB

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

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Hi Jeff, Really well done on the 150th Jaunt! Its astounding how what you have evolved into wearing is so so similar to what I'm up to here in NZ. I am wearing dresses now - as well as skirts, and I too have a shift-dress or sheath-dress as you refer to it. That outfit works really well for you, the pearls look sharp, and compliment it really well. Perfect shoes. Congratulations! A short blazer was suggested which would work, can I suggest a bolero? I would have 10 or so now - because they are so practical. I've picked most of my boleros from thrift stores, and they comein a vast array of cuts and colours and fabrics. I could find and post a photo if it would help. Cheers Heel-Lover

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