The Jaunts of JeffB!

[JeffB]

I'm speechless, but ditto, Steve.   A most interesting tangent to your thread Jeff.

I couldn't agree more, Shafted. Steve brought up some highly intriguing points that I enjoyed reading. By presenting a proper, positive and tasteful image of a man in women's clothes, I help the cause, such as it is by dispelling the caricature quotient. When people stare at me on the street, perhaps they're sizing me up in their minds, and maybe I get them to thinking, "Hey, that guy in the skirt and heels didn't look too bad". By publicly wearing women's clothing and shoes, I'm openly challenging gender convention in terms of what I choose to wear as a man, just like women did decades ago when they donned pants for the first time, and I see that as a good thing.

[SleekHeels]

I can relate to a lot of that Jeff, especially the positive image and "dispelling the caricature". What I like about your style is that women could wear a lot of your outfits with self-respect -  the only reason that men (supposedly) can't wear them with self-respect too is prejudice, and that's what we're challenging, Fashion's a celebration of humanity, you just keep on celebrating Jeff, and inspiring others to do the same.

[JeffB]

I can relate to a lot of that Jeff, especially the positive image and "dispelling the caricature". What I like about your style is that women could wear a lot of your outfits with self-respect -  the only reason that men (supposedly) can't wear them with self-respect too is prejudice, and that's what we're challenging, Fashion's a celebration of humanity, you just keep on celebrating Jeff, and inspiring others to do the same.

 

Thanks for the kind words, SH. I simply do the very best I can, and I'm happy to be an inspiration to others. My singleminded, overriding focus IS to wear what women wear, to look stylish, and, above all else, tasteful, to be anything else would be, in my opinion, foolish because of the still existing (though fading) stigma of men wearing women's clothes being seen by the uninformed as freaks or deviants or clownish. Even if I'm not complimented by the world at large when out and about in the clothes I love wearing, then, at the very least, I want to be respected, the basic right of every human being. And yes, I'll keep on celebrating, my friend!

[JeffB]

Jaunt #229, 6/28/2014: Well, I guess summer is fully in force as the weather was nice and sunny and hot, perfect conditions for an outing, dressed just right for the weather in a light purple embroidered tank top, my 40 inch black peasant skirt, the Payless “Nicole Chopout” platform sandals and a black handbag. For anyone other than myself who's keeping score, this made my fourteenth consecutive outing wearing wedges as they've become my go-to shoe style, and wearing sandals in particular have become great fun for me as it's been more than a little hard to resist them, I just feel so at home in them. As for the long skirt, it's fun to wear too, not to mention very stylish as well, as much as I enjoy showing off my legs, long, filmy skirts really suit me and my personal sense of style, and I love wearing them. Anyhow, my first stop of the day was downtown and a branch of my bank to tap an ATM, after hopping out and feeding the meter, I walked into the bank and while I waited for an open machine, I stood next to an African-American fellow who appeared to be in his early 40's who also waited on a money machine, he glanced me up and down for several moments while we waited, and from how his brows furrowed ever so slightly, I could tell he did appear all that pleased with what he saw, there was just that certain look of revulsion on his face, but he didn't say so much as a word. After tapping the machine, I went inside and strolled up to the counter to get some singles for future use at the meters, got a nice smile from the teller who served me and wished me a nice day, and I smiled back. Back in my car, I drove into town and parked well over a block from the store, which was fine by me because it gave me an opportunity to be seen, and to enjoy the little pleasure that came from how the skirt swished about my ankles while I walked, tall and proud, like all my platform sandals, the Nicoles were crazy easy to stand and walk in and are pleasingly comfortable to boot, increasing the fun quotient of those shoes. Oh, as an aside, much to my surprise, despite the one inch platforms and wedge heels on all my sandals, I've had no trouble whatsoever working the pedals of my car in them.

 

After spending some twenty minutes in the comic shop, I returned to my car, enjoying the stroll and the sunshine, and yes, I was seen by passersby, got a couple of stares, but no other reaction. Once back in the car, it was off to my regular haunts over in South Jersey near Moorestown Mall, today, I dined at Boston Market, enjoying the meat loaf and some mashed potatoes, seriously yummy. From there, I went to the nearby Barnes & Noble for some quiet reading time as I spent nearly an hour there reading sci-fi and sports magazines with a tall iced tea before going to the register with a couple of manga titles, and the whole time, no one paid me any mind. My last stop of the day was to Sears for some shopping, in the women's section of course, and I bought a cute, lace trimmed top in navy and a calf long, blue floral print skirt that matched well with the top and will make for a great outfit with the proper shoes and accessories. I think that the only thing just as much fun as wearing women's clothes is shopping for them! And the more I wear skirts, the more I know I will never go back to pants and jeans. I felt good as I headed back, I enjoyed a good outing and bought more clothes to wear on future adventures which is exciting in itself. More fun to come!

Jaunt #230, 6/29/2014: A new day, a new outing, though a short one, I just wanted to go out and do something since the weather was nice and sunny, but it was also more than a wee bit warm, so I headed out in a black tank top, a 15 inch denim miniskirt, the Payless “Salliana” platform sandals (my fifteenth straight outing in wedges) and a black handbag. Because it was so warm, wearing that mini made perfectly good sense as I was cool and comfortable in it, and, it was fun to show off my legs again, meanwhile, wearing sandals has become somewhat second nature to me lately, when putting together outfits, I've reached for them first as I feel right at home in them, I like how they look on me, and they feel good on me as well. Who knows, perhaps I might spend the whole summer in sandals, it's the perfect shoe for the season. We’ll see. Meanwhile, I headed west into Springfield and Best Buy as I haven't been there in awhile, they've redesigned the store, especially the areas for appliances and TV’s, naturally, I spent the bulk of my time in the store there, ogling the selection of UHDTV’s (Ultra Hi-Def or 4K TV’s) and marveling at how fantastic they look, problem is the prices for them were fantastic too, but, will any and all technology, the cost will come down eventually, so I'll just have to be patient. After well over half an hour, getting no attenti)no ace for salespeople asking if I needed help and being called sir (I expected no less), I left with the discounted version of Abraham Lincoln: Vampire Hunter on Blu-Ray, a cheesy flick, but one I liked. When I left the store, the temps seemed to have gone up, but I remained comfortable in my short skirt. From there, I went down the road to Subway for lunch, the place was empty when I walked in and placed my order, but people filed in as I sat down to eat, and I did get an odd look from a little girl who couldn't have been more than eight or nine, but that was pretty much it.

 

Other people saw me too, I'm sure they, like everyone else were probably taken aback at seeing a middle aged man in a miniskirt and platform sandals and may have had no idea what to make of me. Those were the times when I prepared myself to have someone walk up to me and ask why I was wearing what I wore, I was fully prepared for answers, but no one ever poses the questions, the world simply leaves me to my own devices. The last stop on my brief outing was to a nearby Office Depot as it just occurred to me that I needed a ream of paper for my printer at home, so I went in and bought a ream, pretty as you please. It sure felt good to have gone on that outing, short as it was, but every trip I go on help to further increase my confidence about wear skirts and/or heels in public, while I won't delude myself into thinking I can publicly wear women's clothes and shoes everywhere, but I know I can't, there are still limits to where I can safely go, as long as I have places where I do feel at ease and comfortable in the clothes I choose to wear, that's good enough for me.

[Mr. X]

another fine set of outings for you Jeff.  I relly like that denim skirt outfit!  It looks so cool and comfortable and you described.  Way to go!

[JeffB]

Thanks for the kind words, Mr. X. Yes, that denim skirt was quite comfortable to wear, especially in the hot weather that day. And wearing tank tops has become fun for me as well. All in all, it was a perfectly casual sort of outfit for a Sunday.

[bluejay]

Nice looking ensembles JeffB.

 

Keep up the great choices. And yes, I like to wear sandals and open toe slides too. Tonight I wore brown, Dockers capris, with a light tan polo shirt and my Easy Spirit, 5" wedge heel, open toe, slides in natural patent color. I had a couple of stares from the salesman, at Sears at the tool department. I think that he was shocked to see my bright fuchsia, colored toes, with my wedge heel sandals. Wearing sandals means I must have a colored  pedi too and I'm comfortable with that look.

 

Happy Heeling,

bluejay

[JeffB]

Good for you, bluejay! Funny thing, two years or so ago, you couldn't have paid me to wear sandals of any kind, these days, they're almost all I wear, at least during spring and summer anyway because they're such fun shoes, especially my platform wedge sandals which I just can't get enough of. Pretty darn kooky to say the least.

[JeffB]

Jaunt #231, 8/2/2014:
Wow, hard to believe it's been little over a month since my last outing in late June, but hey, as John Lennon was famous for saying, “Life is what happens when you're busy making other plans”. But that's all water under the bridge as I headed out on a new jaunt after some early morning rain left conditions mild but cloudy, dressed in a blue, embroidered tank top, my 40 inch black peasant skirt, the Payless “Molly” platform wedge sandals (my sixteenth straight outing in wedges) in black and my black faux croc handbag. I've found that the combination of long skirts and sandals to be a good look for me, and I feel comfortable in that ensemble, and since we’re in the warm weather season, I've also come to enjoy wearing tanks too, it all just suits me.

My first stop of the day was to the main branch of the Post Office near downtown as I needed to buy a money order to renew my newspaper subscription. There were half a dozen people ahead of me in line when I entered, and othe a cursory glance from two of those customers, no one paid me any mind while I waited to be served. After I bought my money order, filled it out, put it in the envelope and dropped it off, I was out of the place with so much as a peep from anyone around me and headed into town and my friendly neighborhood comic shop. After parking a block away, I enjoyed a little walk to the shop, even better, since it was breezy, the lightweight skirt whipped about my shins while I walked, got a stare here and there, nothing of significance, par for the course with me, but I don't ever take that for granted. I spent a good twenty minutes or so in the shop before returning to the car, and even though it had been a year since I last wore the Molly sandals, they remain just as comfortable and easy to walk in as ever. And yeah, wearing wedges continues being a real blast for me, I just love this shoe style to pieces.

From there, I drove over the bridge and into South Jersey. Lunch was at Boston Market near the Moorestown Mall, there was a decent crowd in the restaurant, ten to twelve people, but no one paid me much if any attention as I placed my order (meat loaf with mashed potatoes and a bottle of water) and sat down to eat, no big deal. From there, I went to the nearby Barnes & Noble, I got a smile from an older lady whom I held the door for as she left the store, whether she appreciated my outfit, I have no idea. Once inside, I saw right away that there was a fairly large crowd, even for a Saturday afternoon, but again, no one gave me a hassle, chuckled, giggled or surreptitiously snapped pictures of me on their cellphones (something I'm sure has probably happened to me at one point or another on my outings, I'd be foolish to think that hasn't happened), which was fine by me, I don't go out of my way to be noticed, I just want to go where I want, dressed the way I want, I would spend close to an hour wandering the aisles and reading sci-fi magazines in the lounge before going to the register with an anime magazine.

My last stop of the day was to Sears where I wandered the aisles in the Misses department and bought two new skirts and a pretty top. I've kinda lost track of how many skirts I own at present, it wouldn't be an exaggeration to say I have somewhere in the neighborhood of four dozen, give or take a few, I just love wearing them and it's hard to resist something I like and think will look good on me, and I've yet to wear a skirt that didn't flatter me, whether it's a mini, a maxi or something inbetween. More fun to come....

[SkirtDude]

Hi, been lurking for a while, not here go hijack the thread, but want to say you look fabulous, that top is to die for! I've been thru a lot in the past year (stopped the hormone treatment as it didn't agree with me, It was bootleg / fake), started psychotherapy as I had lots of mental issues and have been diagnosed with a form of paranoid schizophrenia, sadly they don't see me qualifying for any hormone treatment as estrogen interacts with the heavy stuff like Citralopram they have me on.

Sorry for the thread I posted last year, I didn't meet anyone, but you are my role model ♡♡♡

Your outfits look great, though I prefer the shorter pencil skirts that show of your fabulous legs and ass to the more 'grannified' look of late. Thankfully the Independent Living complex embraces my choice of clothing, and I'm saving up for some wedges like yours to team with a cute skirt ♡

Looking forward to your next jaunt, don't leave it so long, hon!

[JeffB]

Hello, Kilty! Nice to hear from you. I hope things get better with you. "Grannified" look? Hmm! Interesting. Still, I see lots of women much younger than I in longer skirts, as with everything I do, I follow trends I see other women sport and copy same.

 

Jaunt #232, 8/3/2014:
A new day, a new jaunt as I had an itch to see a movie, so I turned that into a jaunt, going out in a purple embroidered tank top, a 30 inch button down denim skirt which I just bought from Sears during my previous jaunt, the Payless “Nicole Chopout” platform wedge sandals (my seventeenth straight outing in wedges) and a black handbag. The new skirt, with it's button down styling looked nice and looked good on me, and, as you'll see from the pictures, it pairs well with the sandals and tank for a casually dressy look. Meanwhile, I think I'm coming close to another paradigm shift in my evolution as a freestyler as I've gone out of my way to wear more noticeably feminine looking tops of late, when I'm out and about in public, I want people to see that I'm wearing women's clothes, as a male, from head to toe, and it feels very good to wear such clothes. As for the shoes, the Nicoles are fast becoming my favorite sandals, not just because they're so comfy and easy to walk in, the styling is just killer, making them a treat to wear.

But, I digress. I drove straight to my destination, that being a multiplex over in Cherry Hill to see Guardians of the Galaxy. Arriving in the lot a few minutes before it's 11 a.m. start time, I hopped out and walked to the building, once inside, there wasn't much of a crowd, however, a thirtysomething dad with his young son narrowed his eyes ever so slightly at seeing me, then gave me a brief but harsh stare before hustling his kid away, perhaps before the youngster, preoccupied with a lobby poster for a Spongebob Squareparts movie got a good look at me, but the other half dozen people at the counter paid me no mind. As for the movie I went to see, Guardians was pretty darn good, better than I thought it would be, a perfect roller coaster summer blockbuster sort of film that I enjoyed. After the film ended, I walked out into the lobby which was packed with people, more than a few looked at me, but I paid them no mind as I walked past everyone and left the multiplex. I'm sure I probably startled some, but most didn't make any scene.

Back in the car, I headed down the road and drove to Best Buy near Moorestown Mall since I haven't been in the place for awhile. As it was about 2 p.m., there was a good crowd in the store, but again, no one gave me any attention, I guess a middle aged man in a knee length skirt and platform sandals doesn't get much of my rise out of the populace. I would spend well over half an hour in the store, ogling mainly at the 4K hi-def TV sets which are absolutely awesome, expensive too, but hey, that's usually the way things work with new technology on the market. After leaving the store with the Blu-Ray version of Prometheus, I headed home. A good day to be out in a skirt and heels. More to come....

[SkirtDude]

Jeff, bravo! Much prefer this skirt, though I'd be scared of wardrobe malfunctions if a few buttons popped open at the front of the skirt.

I didn't mean any offence, I guess I dress like younger women (not strictly true as they have an aversion to knee length denim skirts, it seems) I just find ankle length skirts a hassle, from stepping over things, to having to answer the call of nature... it's just easier with knee length.

I aim to try and get well, but the wardens here say I will be here for 'some time', so I'm not worried. Everything's paid for, so I'm in no hurry to go and look for work. Though I'm building up a decent wardrobe, more business casual as that's the look I prefer. Some denim, and some cute jeans too. Though some of the medication affects my balance, so no 'killer heels'for now...

Jeff, well done with your jaunts, you are an inspiration. I went out to the shops in a denim skirt today, the bulge in the zip is just that I didn't pull my skirt down and smooth it at the front after it rode up a little , my tummy control briefs keep everything else in order.  I've lost some weight and can get into a size 10 again which is great! I also spoke to my therapist about getting me on more suitable medications that don't make me put on weight and make me so lethargic, and she said she would start to review it and discuss with the care team at the next meeting at the end of the month!

 

http://hhplace.org/gallery/image/4336-dscf0779/

more sensible heels with this skirt, leather boots

 

Looking forward to your next jaunt

[JeffB]

I didn't have any problems with the buttons, the combination of the right size and the stretchy fabric of the skirt made it comfortable and worry free on that score. As for ankle length skirts, I've never had any trouble with tripping or anything like that since the addition of heels keeps that from being a problem. But, I haven't stopped wearing knee length skirts, I just like variety.

[JeffB]

Jaunt #233, 8/10/2014:
I was originally going to go out on a jaunt on Saturday, then be lazy and stay home today, but I decided to be lazy yesterday and go out today. Go figure. Anyhow, I wanted to look casual, so I opted for my black, lace trimmed, V-necked tank top, the 30 inch button down denim skirt which I bought from Sears just last Saturday, the Payless “Molly” platform wedge sandals in black and my black faux croc handbag. The new skirt which I've worn two times straight now just looks so stylish and pairs perfectly with my sandals, speaking of which, every time I've put together an outfit of late, sandals have been the first shoes I've reached for, in fact, they've pretty much been the only shoes I've chosen for weeks now, and with five pairs at my disposal, I have numerous options to pair with just about anything I want to wear.

But I digress. I headed west into the burbs, my first stop being Home Depot as I needed to buy a couple of gardening tools to combat the weeds in my small front yard. Arriving at the store, I hopped out and went right in, after asking for directions to the gardening department (I find it refreshing to be called sir, even when dressed in a lace trimmed top, a skirt and high heeled sandals), I went there and within a couple of minutes, I found the tools I needed. As I headed to the register, I passed a salesperson, a black lady who grinned at me and said, “I want your shoes!” I grinned back and said, “Sorry, I don't like walking barefoot.” That got a belly laugh out of the lady who repeated what I said to another salesperson and she laughed too. Quite a neat little exchange if I do say so myself. After leaving the store, I headed down the road to my home away from home, Best Buy. Once inside the store, I found myself amused at how I stood head and shoulders over everyone in the place, but, I guess that's bound to happen when a six foot two inch guy parades around in near five inch heels, and while I'm sure readers are probably tired of my saying this, but the Mollys, like all my other platform sandals are ridiculously comfortable and easy to walk in, no wonder they've been the only shoes I've worn of late. And yeah, they look damn good on me as well.

After better than half and hour in the store, wandering to and fro with nary a stare, odd look or chuckle from other shoppers, I headed to the register with a real treat, Alfred Hitchcock’s The Birds on Blu-Ray, and I mean to watch it tonight. My last stop of the day was to Arby's for lunch, there wasn't much of a crowd, just four of so diners and no line, so I placed my order, ate and headed back home. A relatively short outing, but an enjoyable one nonetheless.

[SkirtDude]

Loving that cute top! It would go so well with my new pencil skirt I bought the other day It's nice the sales people were so professional and polite, the skirt suits you, though I prefer something shorter to show off my legs whilst the weather is good. Shoes are super cute and I'm digging the necklace ♡♡♡

[JeffB]

Thanks for the kind words, Kilty!

[JeffB]

Jaunt #234, 8/18/2014:
With some time off on my hands and an errand to run, I decided to turn it into a jaunt, one where I pushed the envelope fashionwise as I sported a lace trimmed tank top in coral, the Old Navy black peasant skirt, the Payless “Molly” platform wedge sandals and a black handbag. Because it had been breezy when I left the house around 9:30 a.m., I added my Gloria Vanderbilt denim jacket which matched well with my outfit. Regarding the top, after reading about Thighbootguy having worn a pink top, I thought I'd give that a try, and while what I wore wasn't pink in the truest sense of the word, it was bright enough to be noticed. And, to be honest, it felt rather....empowering to wear such a brightly colored top. Also, in a moment of irony, while I had looked forward to summer where I could prance around in my short skirts, I've been wearing the heck out of my maxis of late, kooky to be sure, but I really like how I look in long skirts, especially when paired with my sandals.

My first stop of the day was to a branch of my bank in the University City area as I had to withdraw some cash to pay a bill, after I parked, I hopped out, paid the meter and walked in, while waiting in line, an older lady who was better that a foot shorter than me asked how tall I was, I said I was six foot two, then, with a grin, I added, “without the shoes”. She then chatted about how everyone in her family was short while I mentioned how my relatives were tall, and she said she admired me for being tall. After withdrawing the money I needed, I left the bank then drive half a mile down the street to the main branch of the Post Office where I bought a money order, filled it out and mailed it off. With business taken care of, it was time for a little fun, so I drove into the northeast and Parx Casino, I place I've only visited in heels and/or a skirt. With temps having risen, I ditched the jacket so everyone could see the coral top, but once inside the casino, I was pretty much ignored as patrons were busy working slot machines to pay any attention to the middle aged guy in a long skirt and heels. My luck with the one armed bandits was only so-so in the hour I had been there, but I did win nearly eighty bucks on a one cent Superman the Movie machine, so it wasn't a complete loss, but I was there mainly to have fun, and I did.

Back in the car, I drove back to town and then over the bridge into South Jersey, heading to one of my favorite haunts in that neck of the woods, Barnes & Noble where I had a turkey and cheese wrap (delicious!) and a bottle of orange juice for lunch which I ate with the newest issue issue of Sports Illustrated, then leisurely read that and a couple of sci-fi magazines for about an hour before leaving with a manga title. My last stop of the day was at Sears for some shopping, and yes, I bought another couple of skirts, namely the 30 inch button down number I purchased two weeks ago, but there were in beige and stonewashed denim. I'll be sure to show them both off on future outings. Oh, yeah, it should also be noted that even though I wore a top that was as close to pink as one could get, I didn't get a rise out out of all the people I came across while I was out and about. Go figure. Maybe guys wearing pink is no big deal in this neck of the woods. More jaunts to come....

[Thighbootguy]

JeffB - I can't quite put my finger on why, but I don't like the tank top style on you when work by itself.  I like it with the jacket, but it just seems too open by itself.  I have a couple of sleeveless turtlenecks that seem to suit my eye, but nothing quite as open as the tank top.  Aside form that reseveration, the outfit loks great!

 

I lucked out in a thrift shop last week (you gotta try that venue).  They had lady's stuff on sale and I picked up six bright colored short sleeved tops, including two in pink.  Considering that most of my tops were black, this was quite a departure for me, but I have been having a great time wearing them.

 

TBG

[JeffB]

JeffB - I can't quite put my finger on why, but I don't like the tank top style on you when work by itself.  I like it with the jacket, but it just seems too open by itself.  I have a couple of sleeveless turtlenecks that seem to suit my eye, but nothing quite as open as the tank top.  Aside form that reseveration, the outfit loks great!

 

I lucked out in a thrift shop last week (you gotta try that venue).  They had lady's stuff on sale and I picked up six bright colored short sleeved tops, including two in pink.  Considering that most of my tops were black, this was quite a departure for me, but I have been having a great time wearing them.

 

TBG

That was a most interesting comment you made about my tank. I agree that it does look nice when paired with a jacket, and when the weather starts turning cooler around next month or so, I'll be sporting that look a good deal, but I also enjoy the open look of the tank as well. Perhaps I might try a camisole which would also look good with a jacket as I'm gravitating towards more feminine looking tops. As for thrift shops, the one I used to frequent in downtown Philly was destroyed little over a year ago in a building collapse, but a new store opened in the western burbs. I will give that a try in the future. Lastly, on the subject of brightly colored tops, while I've worn turquoise and red, it was fun to wear that coral tank yesterday, so you can bet I'll add pink to the collection!

 

Jaunt #235, 8/19/2014:

Another sunny and warm day means a new jaunt, but I did something entirely different today as for the first time since late April if memory serves, I wore traditional heeled footwear, and not just any footwear, but my Pleaser “Vanity” 4 inch heeled thigh high boots (which I'm sure will please Thighbootguy no end) along with my Gloria Vanderbilt denim jacket over a red tank top and a 16 inch black denim skirt. Regarding the skirt, once upon a time, it was 20 inches long, but I took it to my local dry cleaners and had them hack four inches off for the express purpose of wearing it with the boots, and it worked to perfection. As for the boots, after little over three months straight of wearing nothing but wedges, it certainly felt different to be in stilettos again, but it took no time at all to reacclimate myself, especially the pleasingly loud click-clack of the heels. Meanwhile, the red top paired very well with the black skirt and boots, all in all, a very good looking outfit.

And with that, I headed out, west to Springfield, the weather was warm, but not overpoweringly hot, and that made wearing the thigh boots not just tolerable, but enjoyable, comfortable too. And, yes, I had forgotten just how much fun it was to be out and about in thigh boots, not to mention how awesome they looked on me, moreso with the miniskirt than with jeans. My first stop of the day was to Pizza Hut for lunch, after I parked, I went inside, there were only a dozen or so patrons and none of them noticed me as I was seated, then promptly attacked the buffet and ate while watching the Little League World Series. Half an hour or so later, fully stuffed, I left and drove down the road to Best Buy. As I pulled into a parking spot, I noticed a trio of women in traditional Muslim garb, all black from head to toe, given how warm it was, I wondered if they were more comfortable or less comfortable than I was in my short skirt and boots. Once inside the store, it was the usual, but enjoyable routine of cruising the aisles ogling at all the gizmos and gadgets, especially the 4K HDTV sets which I've grown quite fond of, after well over thirty minutes in the store, during which time, no one paid me any mind, I went to the check out lane with a Blu-Ray copy of The Amazing Spider-Man 2 and left.

My third and final stop, driving back the way I came was to a supermarket as I needed to replenish my supply of bottled water. Hopping out, I walked right in, the place was fairly busy for an early afternoon, but again, I wasn't hassled or anything like that, pushing a shopping cart, I went to the aisle where the water was sold, picked up two 24 bottle cases (2 for $7.00), went to the self-service lane, paid for my purchase and left, easy as pie. I was fully prepared for odd looks, gasps, giggles or chuckles, but nothing at all happened, I was treated just the same as everyone else, despite wearing a bright red top, a short black skirt and thigh high boots, footwear that's hardly a staple in August for women, never mind men. And that was very much a fun outfit to wear, I felt daring in the miniskirt and empowered in the boots which literally put me head and shoulders over everyone. You can bet I'll be wearing variations of that outfit regularly once the weather cools. More jaunts to come....

[Thighbootguy]

Jaunt #235, 8/19/2014:

Another sunny and warm day means a new jaunt, but I did something entirely different today as for the first time since late April if memory serves, I wore traditional heeled footwear, and not just any footwear, but my Pleaser “Vanity” 4 inch heeled thigh high boots (which I'm sure will please Thighbootguy no end) along with my Gloria Vanderbilt denim jacket over a red tank top and a 16 inch black denim skirt. Regarding the skirt, once upon a time, it was 20 inches long, but I took it to my local dry cleaners and had them hack four inches off for the express purpose of wearing it with the boots, and it worked to perfection. As for the boots, after little over three months straight of wearing nothing but wedges, it certainly felt different to be in stilettos again, but it took no time at all to reacclimate myself, especially the pleasingly loud click-clack of the heels. Meanwhile, the red top paired very well with the black skirt and boots, all in all, a very good looking outfit.

 

More jaunts to come....

 

JeffB - I will admit to having a biased opinion, but that outfit looks GREAT!  Shoes and  purse match, skirt shows off your legs and the boots, and the necklace over the red top completes the image.  You mentioned, "how awesome they looked on me" which is right on the mark, I could not agree more.

 

I'm not sure where the waist of the skirt falls on you, but consider wearing the skirt with the top tucked under the waist to show off the skirt a little more.

 

I know we differ on this, but I still find it more comfortable to present myself as a guy wearing thigh boots than as a guy wearing pumps.  The boots make such a strong statement hat everything else is either totaly accepted, or totally rejected.  Fortunately very few totally reject the image.

 

I hope you don't wait too long to wear your thigh boots again.

 

TBG

[JeffB]

Hey there, TBG! Thanks muchly for the kind words. I thought you'd enjoy what I wore on my latest outing. Regarding the skirt, it sits snugly right at my natural waist, and works great with the boots. I'll see what I can do about displaying it fully on a future outing, as I mentioned in my last post, wearing the thigh boots felt very empowering and the rush I got from wearing them was quite intoxicating. On the topic of boots versus pumps, I'm perfectly at home in both, I started out with the latter a long time ago while the former was an acquired taste, I see no reason I can't feel comfortable in both. I agree that boots do make a strong statement, but so can the right pair of pumps. It all depends on the person and how HE presents himself in his footwear of choice.

[Thighbootguy]

as I mentioned in my last post, wearing the thigh boots felt very empowering and the rush I got from wearing them was quite intoxicating.

 

Ain't it though. 

 

TBG

[SleekHeels]

Much as I agree with you that wedges are cool, it's nice to know that Pennsylvania is echoing with the click of stiletto heels again And overall that's a very confident and fun outfit. I think the strong colour of the tshirt under the denim jacket balances the strong statement of the boots well. It's great to have the choice of blending in with everyday styles or being more bold and adventurous, and you seem comfortable and confident across the spectrum Jeff.

[JeffB]

Much as I agree with you that wedges are cool, it's nice to know that Pennsylvania is echoing with the click of stiletto heels again And overall that's a very confident and fun outfit. I think the strong colour of the tshirt under the denim jacket balances the strong statement of the boots well. It's great to have the choice of blending in with everyday styles or being more bold and adventurous, and you seem comfortable and confident across the spectrum Jeff.

Thanks for the compliment, SH. Yeah, it certainly was fun to be bold and adventurous with the outfit I wore on Tuesday, highlighted by the boots which had been a treat to wear. And, to be honest, it was a breath of fresh air after dressing so, well, conservatively over the last few months. To have made such a strong statement with an outfit most women wouldn't wear left me feeling emboldened, and eager to strut the streets in that ensemble again, and soon, because I can!

[Mr. X]

Back to the boots, eh Jeff!  That outfit is quite a departure from your other recent choices of garb and footwear.  But you know what, I like it!  I was gonna mention the short skirt but you beat me too it.  As short as it is, it still looks good on you and with the boots.  I have some wedges too but I still prefer heels, be they boots and or shoes.  Anyhow, way to go!

[JeffB]

Thanks much, Mr. X! Once upon a time, I used to be rather self-conscious about wearing a short skirt in public, now it's no big deal, in fact, I love it! At the risk of sounding vain, there isn't a skirt, long, short and inbetween that doesn't look good on me. And thigh boots are terrific, plain and simple!

[Mr. X]

Once upon a time, I used to be rather self-conscious about wearing a short skirt in public

 

You self conscious?  I find that hard to believe.  lol

[JeffB]

You self conscious?  I find that hard to believe.  lol

Hard to believe, but it's true. A few years ago when I wore a miniskirt with my thigh boots, I was so self-conscious because of how short it was, I couldn't bring myself to sit in the silly thing. Nowadays, I don't worry about that, if my skirt rides up when I sit (call me crazy, but I kinda get a thrill out of that), it's no big deal, I'm damn proud of my legs and I don't mind showing them off. I wouldn't wear short skirts if I didn't.

[Thighbootguy]

I remember, several seasons ago, buying a micro skirt at a thrift store.  I asked the register clerk, "How do you wear something that short?"

 

She replied, "Leggings."

 

From expierence, she was right, and it is the only way you can sit down (or even move)  while wearing a micro skirt.

 

JeffB, I recommend one for your consideration (but only with leggings and thigh boots).  If you're gonna show off your legs, there is no better way to do it.

 

TBG

[JeffB]

I will follow your advice. Since I only wear skirts on my outings, leggings with something as short as you described would indeed be essential.