The Jaunts of JeffB!

[JeffB]

I love it! Awesome work sir!!!

 

Many thanks for the compliment!

 

Jaunt #201, 10/2/2013:

After dressing up to the nines for my 200th jaunt, I dressed down for my follow-up adventure, going with a blue polo shirt, my Old Navy 17 inch denim skirt, the Payless "Cori" wedge flats and my crossbody handbag. Because the weather was unseasonably mild, what with temps reaching into the low 80's, more common for August than October, I couldn't resist breaking out one of my short skirts for a short outing as I went to the UPS depot in South Philly to pick up a very important package, namely the three pairs of "Karmen" pumps I ordered from Payless. After a twenty minute drive to the depot, I hopped out and went inside the building, there were only three customers who were already being waited on, a clerk asked if I needed help, I gave him the shipping slip left behind on my door the previous day. Following a brief wait, the clerk came out with the fairly large box which contained my shoes, I signed for the parcel and hurried out, eager to get back home. This was perhaps my shortest outing to date, but it was still an opportunity to go out and about in a skirt, and, as usual, I felt perfectly at ease and comfortable in my outfit, my demeanor in the UPS depot that of just another customer looking to pick up a parcel, I made no big deal about what I wore as wearing a skirt was as natural to me as breathing, and no one else noticed anything either. And that's how I like things to go on my outings.

[Curt]

Jeff, you look quite natural in the skirt. If someone wants to wear a skirt as a guy, this would be it. Good for you for going out in bare legs too! A couldn't do that. There has to be some king of hosiery. Quite a contrast from your last jaunt. Btw, thanks for the link on the dress you wore. I'm going to look for one like that. Hopefully a size 0 isn't too hard to find. I think I have to eat more! I would love to see what you could put together once you get up to jaunt #300.

[Thighbootguy]

JeffB,

 

After that numeric barrage, you have abrogated your privilege of accusing me of over analyzing anything . Having said that… ain’t numbers fun.

 

The blue polo shirt and skirt look great.

 

 

TBG

[fatfuzz]

Well, thanks for the kind words, everybody! Much appreciated! Meanwhile, I had no idea there were members in the Tri-state area. Cool!

 

SleekHeels: You brought up some good points there. I guess I don't mind being ignored, I suppose that means people are willing to let me go my own way just like other people go their own way. And yeah, it is nice to dress up for a jaunt.

 

ilikekicks: Well, I must admit I don't quite know what to say. To have five women staring at my pictures was quite the ego stroking little event. Cool! Many thanks to Granny for the kind words, I guess I do pretty good for 54! HA!

54?? No way!

 

Mind you I get the same - I'm 37 and most people take 10 years off that and are surprised to learn otherwise.

JAUNT #200, 9/29/2013

As promised, for my 200th jaunt (hard to believe I've been at this for as long as I have), I hit the road in a dress for a fairly short, but enjoyable outing as the sports fan in me had to get back in time to file this report so I can sit down to watch my Eagles do battle with Peyton Manning and the Denver Broncos. The dress in question came from Sears and was a sleeveless chiffon dress with a sheer open front jacket. When I saw this on the rack, I fell in love and bought it right on the spot, and it fit like a dream when I got back home. It had a level of style, beauty and elegance that I liked, and, more importantly, it looked good on me. Also, it marked the first time I wore something that wasn't a solid color, which could be seen as pushing the envelope, as was the entire outfit, this was something bold and dynamic, but I was eager to give it a try. I paired my dress with the newly bought Payless "Janine" black patent pumps, off-black pantyhose, a black handbag, and a nice matching necklace. Words fail to describe how good it felt to wear that outfit, and it felt perfectly natural to wear that dress too.

 

My outing was to center city Philadelphia and the Museum of Art which I figured would be the perfect place to wear my dress. After arriving and parking in the garage, I hopped right out, feeling not the least bit anxious or nervous about what I was wearing, and that's the key to this whole business, feeling comfortable and at ease, if you fail and that, you're going to give off bad vibes that people around you pick up, and suddenly, they wonder what's going on with you. But in my case, it was no big deal to wear a dress and heels, and I acted that way as I strolled to the entrance to the museum, the three inch heels of the Janine pumps good and loud. I did get a couple of odd looks here and there as I entered since there was a good crowd inside for an early Sunday afternoon, but I acted just like every over patron who enjoys taking in the wondrous art that the museum had to offer, and I took my time (relatively), strolling throughout the building. Several people gaped and stared and did double takes, thought I heard a giggle but wasn't sure, but no one made a scene, however, there was a positive moment when in the European art section, an older lady came up to me, smiling and one said, "Excuse me, I never thought I'd say this to a man, but I love your dress! It looks fabulous on you. And your shoes are terrific!"

 

I think I blushed, never expecting compliments which I don't get often, but I smiled back and thanked the lady for her kind words, she said she was amazed I looked so at ease in my ensemble and complimented me for being bold before she left, wishing me a great day. That was pretty darn cool to say the least. I would spend another hour and a half, slowly strolling about, the Janine pumps very comfortable for prolonged standing and walking before the time came that I had to leave and get back home. And that was my experience, proving that a man can indeed look good in a dress if he does everything just right. Now I'm eager to wear more dresses because of how great it felt to wear them, and I know I have what it takes to pull it off. And my evolution as a fashion freestyler continues. Now to finish this post and go watch my Eagles in action!

Go on Jeff B!

[JeffB]

Jeff, you look quite natural in the skirt. If someone wants to wear a skirt as a guy, this would be it. Good for you for going out in bare legs too! A couldn't do that. There has to be some king of hosiery. Quite a contrast from your last jaunt. Btw, thanks for the link on the dress you wore. I'm going to look for one like that. Hopefully a size 0 isn't too hard to find. I think I have to eat more! I would love to see what you could put together once you get up to jaunt #300.

Maybe an evening gown. Just kidding! Heh! I most appreciate your saying I looked natural in that skirt I wore today, my goal is to look as ordinary as possible, like what I wear is no big deal, and to me, that's just the case. As for the issue of bare legs, that feels natural to me, and given how hot it had been here this summer, wearing hosiery was a definite non-starter. But, come winter, I envision plenty of outings in tights. Good luck with that dress I gave you that link for.  

JeffB,   After that numeric barrage, you have abrogated your privilege of accusing me of over analyzing anything . Having said that… ain’t numbers fun.   The blue polo shirt and skirt look great.   TBG

Well, you won't have to worry about numbers again until jaunt #250. HA!  

54?? No way!   Mind you I get the same - I'm 37 and most people take 10 years off that and are surprised to learn otherwise.

I guess I look good for my advanced years.

 

Jaunt #202, 10/3/2013:

With a boatload of Payless "Karmen" pumps in my bedroom, I decided to start breaking them in, leading off with the nude patent pair which I matched up with the JCPenney brown polo shirt, my tan Penney American Living skirt and my brown handbag. Since fall is here (though it doesn't feel like it, what with temps in the upper 70's), I thought this would make for a nice, seasonal outfit. My first stop was to the city's main post office for some stamps, after parking, I hopped right out and walked right inside, the heels of the Karmens sharp and loud on the pavement, there were four people ahead of me in line, so I waited patiently, after over five minutes, with half a dozen people behind me, none of whom paid me any attention, I walked up to the counter, bought my stamps and walked out, pretty as you please.

 

From there, I headed into town as the afternoon was young. Now, even though I NEVER step foot out of my house unless I'm one hundred percent satisfied with my outfit, I did express a wee bit of concern about the pumps since I rarely saw anyone wearing nude colored shoes, and I don't want to be seen as being unfashionable. However, it turns out those concerns were baseless as I saw no few than eight women wearing nude shoes, so that put my mind at ease. Needing to tap an ATM, I parked, got out, fed the meter and went to the local branch of my bank nearly a block away. Being in that area of center city at around 12:30, alive with hustle and bustle and crowded with lunchtime crowds on the streets was an absolutely amazing experience as there were so very many women in pencil skirts and heels, dresses and heels, skirt suits and heels, talk about a smorgasbord! And the best part of it all was that I fit right in with the crowd in my own skirt and heels, no one stared, gaped or turned their heads as I walked past, incredible! After I tapped the ATM, I casually walked back, earning virtually zero attention from the crowd, got back in my car and drove off. Being part of that crowd, dressed the way I was quite the enjoyable experience.

 

My final stop of the outing (after some searching for a parking spot) was to Barnes & Noble where, following a half-block walk, I spent well over half an hour in the store, reading the paper with bottle of iced tea and a croissant, and again, no one gave me the time of day, I was just another customer, nothing more, nothing less. This was certainly one of my more pleasant outings as I got to break in a new pair of shoes and enjoyed the nice weather. What could be better?

[Curt]

Hey jeff, I know what you mean about the bunch of women in skirts and heels. I was in the fashion mecca of toronto at bay and bloor streets. There were a ton of women around me in heels. The sound was intoxicating. Are your jaunts more frequent lately? Looking good! Ashley

[SkirtDude]

Looking great Jeff! Love this beige skirt! Really suits your complexion too. You're a snappy dresser ♥♥♥

[SleekHeels]

That's a very well-balanced look Jeff, the length and shape of the skirt works really well and I love the colour combination. Browns and beiges seem to be quite a rarity in the shops these days. I have a sandstone skirt that hasn't made its debut yet, so consider me inspired (as always) !

[bluejay]

Nice look, JeffB.

 

Thanks for the post and pics.

 

Happy Heeling,

bluejay

[JeffB]

Hey jeff, I know what you mean about the bunch of women in skirts and heels. I was in the fashion mecca of toronto at bay and bloor streets. There were a ton of women around me in heels. The sound was intoxicating. Are your jaunts more frequent lately? Looking good! Ashley

 

Thanks for the kind words. Seeing all those pencil skirts has encouraged me to wear them more as they look good on me. As for the frequency of my jaunts, I'm one of those 800,000 federal workers placed on unpaid furlough because of the government shutdown, so I need something to do to pass those unplanned hours.

 

Looking great Jeff! Love this beige skirt! Really suits your complexion too. You're a snappy dresser ♥♥♥

 

A snappy dresser? Well, I don't think I've ever been called that before! Thanks! To be honest, I've never taken my complexion into consideration when I put an outfit together, but yeah, yesterday's outfit did suit my coloring.

 

That's a very well-balanced look Jeff, the length and shape of the skirt works really well and I love the colour combination. Browns and beiges seem to be quite a rarity in the shops these days. I have a sandstone skirt that hasn't made its debut yet, so consider me inspired (as always) !

 

Many thanks for the compliment. That was a pencil skirt of sorts, and the length is quite nice for me. I've only started wearing muted colors like browns and beiges, and they seem to work well for me and are perfect for this time of year. Meanwhile, I'm glad to have inspired you to wear that skirt you mentioned which sounds interesting.

 

Nice look, JeffB.

 

Thanks for the post and pics.

 

Happy Heeling,

bluejay

 

The pleasure was all mine, bluejay. Glad you likes the pics!

[Thighbootguy]

Well, I wear glasses when out and about (but not in my pics because of glare off the lenses) because I'm old and nearsighted (or maybe farsighted). I kinda think they add an aura of sophistication when wearing a skirt and heels. Nothing wrong with looking classy, I try to do that all the time.

 

JeffB - Let us see at least one picture with the glasses (Look 30° to the side of the lens to kill the glare) .  Glasses can change (for better or worse) your whole look.

 

TBG

[JeffB]

JeffB - Let us see at least one picture with the glasses (Look 30° to the side of the lens to kill the glare) .  Glasses can change (for better or worse) your whole look.

 

TBG

 

Hey there, TBG! I gave it a try like I suggested. I don't know if they'll look good, I'll leave that to your judgment.

 

Jaunt #203, 10/4/2013:

With the summer-like weather continuing, I thought I'd wear an outfit better suited for August than October as I went with the K-Mart Basic Editions black v-neck lace trimmed tank top, the I Heart Ronson 15 inch denim miniskirt from JCPenney, the Payless "Molly" platform wedge sandals and a black handbag. The Ronson skirt is fun to wear, and, as I've mentioned on the previous two times I've worn it, since I wear it under a top and without a belt, letting it sit at my natural waist, it looks longer than it really is, but it still shows off plenty of leg and feels comfortable. After being semi-dressed up on Thursday (Jaunt #202), I opted for being purely casual, and I acted casual the entire time I was out and about.

 

Today, I headed to the west, my first stop being Best Buy, I arrived there a little before 11:30, after parking, I hopped right out and casually strolled into the store, there was a mildly decent crowd, a guy who was looking at inkjet printers near the front of the store nearly bumped into me as I entered, and he looked up at me and gaped a little before saying "Excuse me". I can't say I blame him for gaping, in the Molly sandals with their five inch wedge heels (still can't believe how EASY these shoes are to walk in), I'm six foot seven, which is pretty darn tall, and I towered over everyone in the store. I wandered the store for well over half an hour, gazing at all the electrical and electronic goodies Best Buy has to offer which is always great fun for me, I did get an odd stare here and there, but other than having salespeople ask if I needed help on two or three occasions, no one made a big deal of what I wore, and that was my intention from jump street, to be just another person taking advantage of the nice weather to enjoy some shopping. Going to the register with the original Universal Studios releases of Dracula and Frankenstein on Blu-Ray (didn't see The Wolf Man or The Mummy though, I'll have to try another location), my shopping was complete and I left.

 

My second and final stop was down the road to Subway for lunch, hopping out the car, I earned a stare from someone in a car ten feet away as I walked to the store and entered. There was no customers, so I placed my order, sat down and ate, a few people came and ordered, but no one paid me any mind, and that was good enough for me. All in all, a good outing in a miniskirt on a delightfully warm day. Let's see what happens tomorrow.

[Thighbootguy]

JeffB –

 

The glasses look fine, in fact they enhance you smile.  The skirt and top look great.  6’7” is up there.  I’m 6’5” in 5” heels and that lets me stand out but the additional 2” would make a difference.  Watch out for doorways.

 

TBG

[Lime15]

Looking effortlessly great as always! 

[SkirtDude]

You're smiling in your 3rd pic! You've got a cute smile and I looove those glases ♥♥♥ You have confidence and style, looking forward to your next jaunt

[bluejay]

Great look, JeffB. Love those black, wedge heel sandals.

 

Thanks for the post and the pics.

 

Happy Heeling,

bluejay

[JeffB]

JeffB –

 

The glasses look fine, in fact they enhance you smile.  The skirt and top look great.  6’7” is up there.  I’m 6’5” in 5” heels and that lets me stand out but the additional 2” would make a difference.  Watch out for doorways.

 

TBG

 

Thanks for the commentary on the glasses and how they enhance my smile. That never occurred to me before now. And yes, I'm always conscious of doorways when wearing the Molly sandals. HA!

 

Looking effortlessly great as always! 

 

Thanks for the kind words. I do as best I can. It should be noted that it takes a goodly amount of effort to look effortlessly great.

 

You're smiling in your 3rd pic! You've got a cute smile and I looove those glases ♥♥♥ You have confidence and style, looking forward to your next jaunt

 

Thanks for the kind words on my glasses! That's a first! HA!

 

Great look, JeffB. Love those black, wedge heel sandals.

 

Thanks for the post and the pics.

 

Happy Heeling,

bluejay

 

Thanks! I love wearing those sandals too!

 

Jaunt #204, 10/5/2013:

With summer in October continuing, I headed out for a new jaunt, wearing my K-Mart blue campshirt, the Old Navy dark denim 17 inch skirt, the Payless "Cori" wedge flats and a black handbag. Because it was so warm out (temps reached into the mid 80's), wearing a miniskirt seemed like the right thing to do on a day like this, and it was a good decision as I felt perfectly cool and comfortable, in fact, it actually felt liberating since I got to show off my legs, and that made things all the more fun as my goal for the day was to look as casual as possible, and the Cori flats are a definite favorite for my casual outings.

 

My first stop of the day was downtown to visit my favorite comic book shop, after parking a block away, I hopped out, paid the meter and strolled down to the shop, passing a beefy homeless man sitting in front of a closed down movie theater who's eyes widened, mouth fell open and his head swiveled as I walked past. I spent a good twenty minutes or so in the shop, no big deal, after leaving the store and heading back to my car, I passed by the same homeless man who gaped at me a second time, guess he wasn't used to seeing someone like me. Heh! From there, I drove into South Jersey and headed to the Moorestown Mall area, stopping at Chick-Fil-A for lunch, there wasn't much of a crowd in the store when I entered a little after noon, placed my order and ate without incident. My next stop was to the nearby Best Buy, once again, I confidently strolled into the store, earned a couple of stares here and there, but no big deal as I spent well over half an hour in the store, mingling with other shoppers, unfortunately, I couldn't find the Blu-Ray version of the original Wolf Man, so I had to settle for leaving the store with Iron Man 3.

 

My last stop of the day was to Barnes & Noble, after half an hour spent gazing over magazines, I headed to the video area, and when I was there, I passed a couple of African-American gentlemen my age, one of them, his accent seemingly Jamaican looked me up and down, then asked if I was wearing a skirt, I nodded, grinned and said yes. Guess he couldn't tell that I was. And that was it, but I found that little exchange mildly comical. Another pleasant day of freestyling as I took advantage of the warm weather to have fun.

[Steve63130]

Hey, Jeff! I've been out of town for the past 10 days on vacation and just got back. I'm catching up on the missed threads, so please accept my belated congrats on your 200th outing (and then some!). Looking great! You're doing a great job in keeping Payless in business. Tell them I said you deserve a free pair or two. lol

 

Steve

[Foxyheels]

Loving the outfit in Jaunt 202 Jeff, the colour and style suit you perfectly and the fit is amazing for your physique. A great example of free styling, you remain our number 1 example and pioneer. Keep up the good work. 

[JeffB]

Hey, Jeff! I've been out of town for the past 10 days on vacation and just got back. I'm catching up on the missed threads, so please accept my belated congrats on your 200th outing (and then some!). Looking great! You're doing a great job in keeping Payless in business. Tell them I said you deserve a free pair or two. lol

 

Steve

 

HA! I'll go to my neighborhood Payless and make my demand! Thanks for the kind words.

 

Loving the outfit in Jaunt 202 Jeff, the colour and style suit you perfectly and the fit is amazing for your physique. A great example of free styling, you remain our number 1 example and pioneer. Keep up the good work. 

 

I appreciate the compliment. I liked that outfit a lot too. I'm glad that I can be seen by folks like you as a top example of freestyling, and I'll continue to do the very best I can.

[JeffB]

Jaunt #205, 10/19/2013:

With the weather transitioning from the August warmth of the previous couple of weeks to more traditional temps for this time of year, I dressed for the occasion as I headed out for a little outing in a Gloria Vanderbilt denim jacket from Sears over a long sleeved magenta scoop neck t-shirt, a 16 inch black denim skirt, the Payless "Tara" knee boots and a black handbag. Before I continue, let me give you a little history on the skirt, originally it was 20 inches, but I thought it would look better at a shorter length, so I took it to my neighborhood cleaners and had them take four inches off. VOILA! Instant miniskirt, and I love how it looks on me, especially with the Tara boots.

 

Headed into center city, I stopped off at a branch of my bank for some cash, getting a homeless guy to swing his head around and gape at me as I walked by, but that was the only reaction I got while I was there. My next stop was to my favorite comic shop in the downtown area, after parking halfway down the block, I strolled to the shop, passing a few people who didn't give me any attention. In the shop, I spent a good twenty minutes before heading to the register where I got a pleasant surprise, the person working the register was a twentysomething Asian woman who smiled and told me she liked my boots, I smiled back and told her I had them for over six years and they fit like a dream. As always, it was cool to get a compliment on my attire. Pretty cool. From there, I strolled around the corner to a nearby convienience store for a newspaper, getting no reaction save for a turned head here and there, nothing more than that.

 

Returning to my car, I headed over into South Jersey and to Boston Market near Moorestown Mall for lunch, I did get another couple of turned heads as I stood in line to give my order, but was left alone while I ate. My final stop of the day was to the nearby Barnes & Noble where I spent little over half an hour, wandering the magazine racks, sat down in the lounger area to read through a few, putting the boots on full display for all to see, and while the skirt rode up while I sat, I didn't mind at all, in fact, I enjoyed showing off my legs which I had crossed. Must've been the exhibitionist in me, otherwise, I wouldn't wear miniskirts at all. Heh! Another pleasant day of freestyling and I had fun, and that's the goal of what I do. Meanwhile, I've arrived at the decision to finish the year wearing skirts, with chillier weather on the way, I'm eager to break out all my long skirts and pair them with my knee boots. Should be great!

[Jimnj3]

Very good look for you Jeff! A very nice outfit!!   Maybe even a higher heeled boot next time?

 

Jim

[Mr. X]

Looking good Jeff!  You look very comfortable in that outfit!

[Shafted]

Looking good Jeff. Still don't know how you pull off that look so well. Could it possibly be self-confidence? Duh.

[SleekHeels]

Fantastic Jeff, I think that's my favourite of all your outfits, the style, the colours, the proportions are perfect! The whole look oozes a relaxed,  positive self-confidence, a real feel-good combination. No doubt you'll agree that the outfit definitely looks more complete with the bag. Just an idea for when you re-visit this outfit, maybe a subtle silver necklace would be a nice touch too, though it sure is 10 out of 10 even without that.

[bluejay]

Love your look, JeffB. that skirt and knee boot comb , rocks with confidence, that you are showing. Great work! Keep 'em coming!

 

Happy Heeling,

bluejay

[SkirtDude]

Looking great! I wouldn't have the confidence to wear something so short, but you pull it off well, hon ★★★

[JeffB]

Thanks for the kind words, everybody! I greatly appreciate the compliments. I sure had a LOT of fun wearing that miniskirt and boots which made me feel, well....sassy. HA! Perhaps I've found my niche when it comes to wearing short skirts, after all, I certainly have the legs for them! Double HA! But seriously, yes, it IS all about having confidence, otherwise, I wouldn't be able to do what I do. I feel that every jaunt I go on is a brand new adventure filled with all sorts of possibilities for enjoyment and personal fulfillment, and Saturday cemented the tremendous joy that comes from freestyling and wearing what I like, not what society dictates I wear. If I want to wear women's clothes and shoes in public, that's my prerogative, not anyone else's. And more fun is to come!

[SF]

Jeff, Nice stories, it is good that you can go out dressed how you like.  6ft 7inches, with 5 inch heels, wow...  You would tower over everyone else.  I am 6ft 3inches and try to keep my heels to less than 3 inches, to avoid the "towering" effect as well.  

I am out in heels as much as possible (in guy mode), not sure if I will ever "jump the shark" and go gal, ha ha.  I find heeling is fun and enjoyable, too bad more folks here don't have the opportunity to do it more often.  Take care...  sf

[Shafted]

For me, towering over everyone else is awesome. Again this is all about self confidence. I can preach this all day long until I'm blue in the face. If you want to be able to wear anything you desire, you only need do it. It may take some intestinal fortitude, but it is so worth it.