The Jaunts of JeffB!

[Shafted]

WOW! That is just amazing Jeff. It really makes me wonder what is holding society back.

[Foxyheels]

Congratulations on number 100 Jeff. Your positive attitude to dressing exactly what you want is an inspiration to us all. You clearly present yourself as a man and are very comfortable with your fashion choices. From your posts I assume you are mindful of where you go and thus don't meet the idiots in our society too often. I think you will rarely get anything other than the 'double take' reaction ( which I personally find amusing when it happens) due to your confident attitude. I applaud what you do as you really are a pioneer for men in heels, I look forward to reading about the next 100 jaunts.

[JeffB]

kneehighs: I appreciate your kind words, being that you're such a fashion expert. Not only did I look good, I felt good too!

SleekHeels: In retrospect, I suppose that the blazer I wore did work better with the dress than the one I had ordered, but yeah, I'm interested in seeing what that other one looks like once I finally get my hands on it. And no, I never took off the blazer the whole time I was out as I would've felt awkward showing off my shoulders. As for accessories, it occurs to me that a strand of pearls would've worked with the color of the dress. Hmm! Something else to consider. Heh!

Shafted: I also wonder about that! HA!

Foxyheels: Oh, yes, I am indeed mindful of where I go as I'm always careful and cautious about my surroundings, which is why I only venture out in daylight where I feel safer than I would at night. Thanks for calling me a pioneer. I simply do my best to present a positive image of a man in heels (and occassionally more).

[skirtedvik]

I like the dress and as far as I am concerned it SUITS you!Try other type of blazer,not a man's one is my suggestion.For the record - I like broad shoulders and I possess a pair of them and it looks good in a different way while wearing a beautiful outfit.

[roniheels]

Jeff,

I really like the look but especially the blazer with the dress. And I am sure there were others who probably wanted to tell you what the one woman said to you. You looked very stylish and professional in that outfit. It seemed as though this was a possitive jaunt. Congratulations!

[JeffB]

skirtedvik: Thanks for the kind words. I will admit I wasn't entirely certain if I could pull off wearing a dress without looking odd or stupid, but I was determined to go through with my experiment, and I was glad I did since I had such a good time. Suddenly, I want to wear a dress again in the future, and I most definitely will. roniheels: Stylish and professional, eh? Well, yeah, that's one way to describe my look, and it fits because I strive to always look my best while out in public, in fact, I sometimes obsess over that since my goal is make people think: "Hey! That guy looks good in his skirt and heels!" And the operative word here is "his", my goal is not to crossdress, while that's how society would view what I do, rather, I simply wear the clothes and shoes I like, who cares if said items come from the women's side of the store.

[JeffB]

Nutty as I am about numbers, her's a full breakdown of what I've worn after 100 jaunts:

JAUNTS BY YEAR

2008: 10

2009: 42

2010: 28

2011: 20

SKIRTS/DRESSES

Above knee: 41

Below knee: 20

At knee: 3

Skorts: 2

Dresses: 1

PANTS/JEANS

Jeans (tucked in boots): 19

Jeans (worn untucked): 12

Pants: 1

Capris: 1

FOOTWEAR

Knee boots: 23

Thigh boots: 19

Ankle boots: 1

Pumps: 41

Loafers: 16

I found it fascinating that since I began this thread, I've worn skirts twice as much as jeans and/or pants, or that I've worn boots a fraction more than pumps which I love. Go figure. But hey, it's all very much part of the fun of freestyling, and I'm having more fun than ever since I began this thread, and I plan to keep on having fun for quite a long time to come. So, check back here when I reach my 200th jaunt!

[Thighbootguy]

JeffB – Sorry I’m the last one showing up at the party (the browser at work blocks images).

The outfit looks great. The blazer and the handbag make the whole thing work and produce an excellent result. It’s a great example of how to combine things to produce a nice overall look.

I guess I never will understand wearing pumps. To my eye boots (even knee high) would have worked very well. Maybe when the weather permits you might give that look a try.

It sounds like the outing, though uneventful, was a lot of fun, especially the nice complement at the end.

Isn’t it amazing what presenting a confident image will do?

[JeffB]

TBG: Thanks for the kind words! And don't worry about being late, better late than never. I'm glad to have read that you liked my outfit. By the by, I told you I'd wear a dress, didn't I? And it was a thrill and a half! On the topic of pumps, I've always loved how they look and how they look on me. Long, gorgeous legs like mine just plain POP in pumps, oh, sure, the effect is pretty much the same in boots, but I'm comfortable wearing the world's sexiest shoe.

[tallguyinheels]

Excellent on both fronts, Jeff. I like that you have elevated yourself to the 5" heels and, wow, the dress is stunning. I couldn't imagine myself in that. Yesterday, I was out in new boots, Domina thigh boots - with 6" heels - the big noticeable difference - as you experienced - is the need to take shorter strides. Though a great opportunity , as you stated , to enjoy the experience. Well done.

[skirtsnhose]

6/5/2011:

All in all, it was quite a fun experiment, having pushed the envelope yet again by wearing a dress and living to blab about it here. Heh! . . . Do you think I was nuts to have done what I did? Perhaps, but I've probably done crazier things than this, so it doesn't matter in the end. In the meantime, I'll build on what I've done and strive to improve and do better the next time, should one come to pass. Does this mean I'll go out in a dress again? Maybe, because it had been thrilling, I won't rule out another venture in the future.

That wasn't so bad, was it? Dresses are a fantastically comfortable way to freestyle, and they can be a ton of fun. I've been adding a couple here and there to my wardrobe myself, and I've been finding the public response has been neutral to positive, just as you found out.

Bravo on your major freestyling achievement, JeffB!

[JeffB]

tallguyinheels: I must say I enjoyed the challenge of wearing five inch heels (which will be my limit for public outings), and it proved to have been easier than I thought once I got the hang of them. Weather permitting, I plan to wear them again on Saturday or Sunday. skirtsnhose: Nope! Wearing a dress wasn't so bad at all! In fact, it had been a lot of fun, moreso than I thought. And, after a while, it felt as comfortable to me as wearing heels, and that only increased the overall enjoyment of my outing. And yeah, I plan to wear a dress again in the future.

[Thighbootguy]

tallguyinheels: I must say I enjoyed the challenge of wearing five inch heels (which will be my limit for public outings), and it proved to have been easier than I thought once I got the hang of them. Weather permitting, I plan to wear them again on Saturday or Sunday.

Hmmm... If memory serves you have a pair of black knee high boots with 5" stilettos lurking in the closet somewhere. Strikes me they would look great with the dress and jacket.

[JeffB]

Hmmm... If memory serves you have a pair of black knee high boots with 5" stilettos lurking in the closet somewhere. Strikes me they would look great with the dress and jacket.

Really? I don't have anything like that in my closet! However, that's not a bad idea!

[JeffB]

#101, 6/11/2011:

After dressing up to the nines last Sunday, I decided to tone things down a bit for today's outing which was shorter than usual because of unstable weather and a day long threat of thunderstorms. Here's what I wore:

A denim blue camp shirt, my black Old Navy skirt, bare legs and the Payless "Katie" loafers. While the skies were overcast, the temperatures were cool and comfortable while I drove into town, and, hopping right out after I parked, I felt comfortable in my casual outfit as I strolled across the street to an ATM for some cash, attracting a couple of stares from passersby, nothing more. From there, it was off to my local comic book shop where I spent a good twenty minutes, then I walked around the corner to a nearby convenience store to buy a newspaper, all the while, it was fun to be seen and, for the most part, no one paid me much, if any attention, though, while on my way back to my car, I passed an older black gentlemen who's eyes widened and he turned his head to get a good long look at me while we passed. However, he bade me a good afternoon, and I returned the greeting. Whether or not he gave me a double take I have no idea.

From there, I drove to the always busy and lively Rittenhouse Square area where, after taking a good twenty minutes to find a parking space, I hopped right out to walk around and to be seen. I walked through the park at a slow pace, acting cool and calm as always, a few people craned their necks at me, but considering that hundreds of people were in the park, that small percentage was no big deal. While waiting for a traffic light at a corner across the street from Barnes & Noble, a white woman in her early 20's I guessed looked me up and down, then, with a smile said, "Nice skirt. It looks good on you." I smiled back and thanked her as the light changed and I crossed the street. That made me feel happy, knowing I presented such a proper image that someone felt compelled to compliment me, regardless of the fact that I was wearing an article of clothing not normally seen on a man. And, guys, THAT'S how we defeat that stigma regarding men and women's clothing.

Walking into Barnes & Noble, I retreated to the second floor lounge area where I enjoyed a bottle of lemonade while reading my newspaper. The lounge was full, but no one paid me much attention. After about an hour (remembering the time I had on the meter), I packed up and left, walked back to my car and drove back home. While my outing was short, it was satisfying as I was able to stroll through a busy downtown area in a skirt and wasn't made an object of derision. That made my outing very much fun.

[Mr. X]

#101, 6/11/2011:

After dressing up to the nines last Sunday, I decided to tone things down a bit for today's outing

It's interesting how are mindset and wording of our postings change depending on how far each individual has progressed. Or where are comfort levels are at when we are out and about. Your at a level where a dress is considered dressed to the nines. Yet a skirt is considered dressed down.

Next guy comes along and says yesterday I was wearing my 5 inch heeled boots with jeans. I was toned down outfit wise. Today I switched it up and put on a skirt and loafers for the first time. I was dressed to the nines....lol

[JeffB]

It's interesting how are mindset and wording of our postings change depending on how far each individual has progressed. Or where are comfort levels are at when we are out and about. Your at a level where a dress is considered dressed to the nines. Yet a skirt is considered dressed down.

Well, it was a casual skirt! That makes all the difference!

[JeffB]

#102, 6/12/2011:

After a jaunt on an overcast Saturday in a skirt, I decided to spend an overcast Sunday in jeans. Makes sense, right? Right! Anyhoo, here's today's outfit:

The main reason for my jaunt today was to put in more time wearing the Pleaser five inch heeled "Seduce" pumps, to break them in so they'd become more comfortable, and get myself more used to the taller heels. I had enjoyed my first outing in the shoes last weekend and was eager to wear them again. As luck would have it, I needed to go to a computer store in the western 'burbs for a VGA cable for an experiment I wanted to conduct with my laptop and bedroom TV set, so off I went. Wearing the Seduce pumps also offered me a chance to acclimate myself further to driving in five inchers, and, I'm happy to report that it's very much a breeze. I arrived at the store a little after eleven, just after the doors opened, so I hopped out and strolled in, remembering to maintain proper posture and to walk with smaller steps than I would with shorter heels.

No sooner had I entered the store that I was reminded of the perils of high heels on slick tile floors as I felt my left foot slide out from under me, however, I was quickly able to reorient myself before suffering the embarrassment of a tumble. Maintaining my casually cool expression, I went about my business of searching for that cable I needed which I found, there was a decent crowd of shoppers in the store for late on a Sunday morning, but no one paid me any mind, save for the occasional salesperson who asked me for assistance, because it's a store with computers and gadgets and all sorts of geegaws, I would up spending nearly half an hour in the place before finally going to the checkout with my purchase. My mission accomplished, I then drove to Springfield and Borders where I relaxed in the lounge area with a cup of iced tea and some magazines to read, now, I did attract a couple of turned heads as I sauntered to the lounge area, no doubt from the sound of the heels, but nothing more as I spent an hour there.

After Borders, it was off to Best Buy to wander and otherwise goof off there, inside the store, I caught another of turned heads but again, nothing more, despite how crowded the place was, verifying what I've always known and related to nervous newcomers in this thread: that people are too wrapped up in their own lives and affairs to worry or care about a guy wearing high heels, and even though I probably approached six foot seven in those five inchers, I garnered next to no attention. I've probably said this a time or two as well, that I can't help but feel empowered when wearing heels, like I'm standing head and shoulders over the crowd, a feeling that's good for the ego. Meanwhile, I was becoming more acclimated to the taller heels of the Seduce pumps, it was still a wee bit of a chore to maintain posture and whatnot while walking, not to mention taking those all important smaller steps, especially on tile, and yes, it did tire me out just a wee bit, still, it was a lot of fun. And that's the important thing.

[Shafted]

JeffB, You are obviously finding out what myself and I'm sure others have found. The higher the heel the more magic they possess. I wear 4 inchers quite a bit, but when I go to my 5 inchers, I can't quite explain the feeling, but they are very empowering.

[roniheels]

Congratulations on two fine, fun jaunts. I am sorry to hear of your tumble, but sounds like your recovery was smooth. I know one day I will take a tumble in high heels, but as of yet, I'm happy to report, no fall yet.

I haven't been back to Best Buy in high heels yet. I have a day off this week, so I think I am going back in there just to prove I'm not intimidated by the looks and stares. I'll let everyone know how it goes.

[JeffB]

Shafted: Yes indeed! Like I said, I had felt empowered in those taller heels. Quite an entertaining feeling to say the very least, and a most enjoyable one too. Oh, I'm sure I could feel the same way in four inchers, as in "I'm bold enough to thumb my nose at society by wearing high heels", but there's something entirely different about fives. And it's great fun as well! To stand tall and proud in the shoes you love while carrying yourself with class and style is a tremendous sensation. roniheels: Not to worry, it's not like I wound up on my bottom for all in that computer store to see, but I think that if I hadn't caught myself and reestablished my balance, I probably would've fallen. Like you, I know that's going to happen sooner or later, and happen in someplace VERY public, I just have to be on my guard against it. Eternal vigilance and all that rot. As for Best Buy, go for it! You'll never know what might or might not happen until you take that dare and see what happens.

[SleekHeels]

I agree, I do find the extra height empowering even with my 3½" ankle boots I've worn a couple of times, even though that only takes me to about 6 foot tall. I guess it's relative to what we're used to in flats, just seeing the world from a little higher gives that psychological boost. The boots are quite stable and make it easy to walk confidently. However, my last outing was my first time in my 5" pumps (I'll post when I've had a chance to take photos) which is a pretty teetering height for my UK7's and I found that even though I had to walk much more carefully, I felt a different empowerment, not from the extra height but just from the feeling that I was coping with the heels elegantly and also coping with (maybe even enjoying) the attention from having to walk much more slowly in everyone's view - it's like time slows down and you can savour the moment.

[JeffB]

Jaunt #103, 6/19/2011:

Even though temperatures threatened to reach into the upper 80's, I was determined to go out on a jaunt, especially after being too lazy to have done so the previous day, and, it was enjoyable. Here's what I wore:

A white camp shirt with my Old Navy peasant skirt, bare legs, the Pleaser "Vanity 2013" pumps and my black faux croc print handbag. By my own admission, I was perhaps a smidgen overdressed as I was off to the Borders bookstore in Springfield to spend some quality time with my laptop, but I'm something of a slave to my own personal edict that demands I look my very best when out and about in a skirt and heels. I have to set a particular standard when it comes to my mode of dress, so it stands to reason that I'll stand out in a casual setting, like a bookstore. Anyhoo, I arrived at the store about five minutes before it opened, without a care, I hopped out with my bag that held my laptop and strolled to the door. A crowd of little over a dozen people were milling outside as I approached, men, women and kids, a few of them looked me up and down, especially the kids, but no one said a thing as, like them, I bided my time until the doors opened.

Once inside, I made my way to the lounge area, set up my machine, then went to the counter for a medium iced tea before sitting down (casually smoothing my skirt before I sat) to goof off online and do some writing. For the next three hours, I was in my own little world, but, every now and then, I noticed out of the corner of my eye, a few people giving me a quick once over as they walked by, nothing more, I was left alone, and that was fine by me. Well, kinda, I wished at least one person had approached to ask why I was dressed the way I was, however, that wasn't the case. Shortly after two, I packed up and left, my next stop being Best Buy as I needed to buy some new rechargeable batteries for my camera. Once again, I hopped out of the car and strolled right on into the store, in the more crowded, noisier atmosphere (the only time a Best Buy is bookstore quiet is when it's closed), I attracted a goodly number of more stares, and, at one point, heard someone whisper, "Goddamn!" from behind my back, but I chose not to respond.

After little over thirty minutes of wandering the aisles (it's impossible for me to just go into a Best Buy, grab what I need and leave), went to the cashier with my purchase, and as I reached into my bag for my wallet, the cashier, a young woman rang grinned and said, "Nice bag." Now that was certainly out of left field, despite the skirt and the heels, what she noticed most was the handbag! HA! Go figure! I grinned back and thanked her. From there, it was back home so I could type up this report, then relax to watch the Phillies play. To be honest, I don't know what to make of that little encounter with the cashier, other than it was ironically humorous, not to mention remarkable how people will take notice of one particular thing and ignore pretty much everything else. I mean, let's face it, a guy carrying a handbag is not exactly a normal occurrence, even when garbed in men's clothing, in my case, it was doubly above "normal", but hey, it made for nice interlude.

In any event, I got to enjoy another jaunt, and earned myself a pleasant little surprise to boot, and for me, that's all part of the total freestyling experience.

[Mr. X]

as I reached into my bag for my wallet, the cashier, a young woman rang grinned and said, "Nice bag."

Don't you just love getting little comments like that. I do admit is was strange of here to comment on the bag though the way you were dressed.

[SandalFan]

To be honest, I don't know what to make of that little encounter with the cashier...

I think she might've been compelled to say something, but wanted to be nice about it, and your bag was the one thing she liked.

[roniheels]

Nice Jaunt, Jeff. I know what you mean when you say you are hoping for more comments to go with the reactions. As far as the girl at the checkout, I'm with you. I'm not sure if she really didn't notice your entire attire. Or if she was being sarcastic by just commenting on your bag. I have not yet been back to Best Buy. But on my next outing I mean to do so. Thanks for the latest update.

[JeffB]

Mr. X: Indeed! It's why I so enjoy my little adventures, mainly because I never know just what will happen, or what someone will say to me. And that compliment on my bag truly took me by surprise. SandalFan: Perhaps she was, but she didn't say anything else, other than to thank me for my business. roniheels: No, I don't think there was any sarcasm there. I'm guessing she didn't see my outfit when I approached her register, I don't know for sure. Still, it made for a curious little interlude.

[Mr. X]

Mr. X: Indeed! It's why I so enjoy my little adventures, mainly because I never know just what will happen, or what someone will say to me. And that compliment on my bag truly took me by surprise.

I feel the same way when I am out and about.

[JeffB]

Jaunt #104, 6/25/2011:

After three straight days of miserably hot and humid days with thunderstorms lurking about, Saturday, while warm wasn't as humid, so it was time for a jaunt. Here's my outfit:

The white camp shirt with my Penney's a.n.a. jeans and the Pleaser "Seduce 2013" 5 inch heeled pumps in black patent. After having enjoyed two previous outings in those five inchers which I'm slowly mastering, I thought I'd take the patent pumps out for a spin. Paired with the dressy camp shirt and my favorite jeans, I thought I presented a darn handsome image, perhaps moreso than normal for a lazy Saturday. My first stop was downtown to tap an ATM for spending money, once again, the key to walking in five inch heels is short steps, not long strides which I had been long used to taking in three and four inchers, the physics of such strides in high heels is flat out impossible, and taking those short strides irked a motorist turning onto the street I was crossing (I could see the annoyance in his face), but I wasn't about to rush, again, such a thing in those shoes was out of the question.

After getting my money, it was back across the street (while catching the notice of a guy crossing the other way), into my car and off to my local comic shop. Walking nearly a block from where I parked to the shop afforded me the opportunity to further break in the new shoes, taking short strides and looking calm and cool while consciously trying to avoid the little spaces between sections of sidewalk that can catch and wreck a heel tip, something I've had happen to me more times than I can count while wearing thin heels. Once in the store, I spent a solid twenty minutes there, picking out new stuff then chatting with one of the guys who works there about the Green Lantern movie, how it was decent, but not great. From there, it was back in the car and over the bridge into South Jersey, stopping at the Cherry Hill Mall for lunch and a bit of shopping. Something else to keep in mind when wearing higher than normal heels, making sure your footing is good on tile floors, well, I'm proud to report I didn't suffer so much as one slip.

The food court was fairly full, though I've seen it plenty well packed, a few people noticed the shiny toes of the pumps peeking out from under the hem of the jeans, and, no doubt the heels as well, but other than said glances, no one bothered me, nor did anyone titter, giggle or chuckle at the guy wearing glossy women's shoes. I ordered from Subway (which I love) and ate in peace, again, no one gave me so much as the time of day beyond a few stares and double takes, Once I finished, I headed into Penney's which was near the food court for the aforementioned shopping, and no, men's attire was the furthest thing from my mind as it's fun to shop for women's wear, after some twenty minutes perusing the aisles, I settled on a sharp looking black denim skirt with copper buttons on the front pocket flaps, it's short (measured at 20 inches) and sleek looking, just the way I like my skirts. Even better, I caught a half off sale and paid all of around $21.00. Not bad, not bad at all. I'll be sure to show it off for everyone at my earliest opportunity.

Next stop, the Barnes & Noble bookstore near Moorestown Mall where I spent almost half and hour cruising the aisles and being relatively ignored, save for one young black lady who's eyes widened and jaw dropped when I walked past. After buying a couple of manga (Japanese comics) titles, it was off to the Moorestown Mall itself for a particular task, I entered the Sears store and walked through into the mall where I went to a watch repair kiosk to have the battery in my men's watch replaced since it died on me the previous evening. I was told by the person who waited on my that it was take little over five minutes, so I went back into Sears to kill some time, but it proved to be time well spent as I found a charming navy skort which was around the same length as the skirt I had bought at Penney's, so I snatched that up, spending little under twenty bucks before returning to the kiosk to pick up my watch. The whole time, I did catch more than a few glances and stares, but then, when you wear patent high heels, that's to be expected.

All in all, a darn good outing. I still feel that I haven't fully mastered walking and standing in five inchers, even after this, my third outing in them, but it's coming along nicely. Heck, Rome wasn't built in a day, so I can afford to take my time. Admittedly, I felt the strain in my calves, and my feet were throbbing more than a little, but that was to be expected since I was breaking in new shoes on the street, another outing or two, and they should be good to go. Ahh! Such fun!

[Mr. X]

Wow Jeff! I almost didn't recognize you in those jeans...lol. You better put your skirt back on or people will think your weird or something...lol