The Jaunts of JeffB!

[JeffB]

In deference to those that have a great deal more experience dressing up and appearing in public than I, I think it would be a big mistake to change your style to that of wearing more "eye catching" outfits in public. Unless, of course, your objective is to attract attention, such as TBG does, and not blending, like you obviously do.

Not to worry. My idea of being "outrageous" would be wearing a shorter skirt and higher heels, and, come to think of it, I've already done that on a previous outing with my miniskirt and thigh boots. However, I don't plan on altering my mindset when it comes to my outfits all that radically. At the heart of the matter, I'm very much a conservative dresser, and that will never change.

[JeffB]

7/19/2009:

Another Sunday, another outing. Golly gee whillickers, what a boring routine! HA! But seriously, folks, with warm, sunny weather to take advantage of, I went out on a new jaunt today. In my neverending mission to explore and expand on my personal sense of style, I decided to experiment and make like Johnny Cash by wearing all black as you can see below:

My JCPenney polo shirt, 20 inch Old Navy skirt, short strapped handbag (of late, it's become indispensable to me), bare legs and the Payless "Lance Flex" pumps. Deciding to go all black today came after spending nearly an hour that morning testing a variety of outfits before deciding on what I wore. As I've said before, wearing a skirt has become quite natural to me, and I feel a little more bold and confident each and every time I wear one. Oh, yeah, and it's lots of fun too.

Just a short outing, but an enjoyable one. First stop was to what I now call my regular hangout, the Borders bookstore in Springfield, after I arrived in the lot and climbed out, I passed a guy leaving the store and headed to his car, his eyes widened when he saw me but he said nothing as I went my way and he went his. A few months ago, I would have felt self-conscious, now, I let that stuff pass, I already know people are going to stare as as a man in a skirt and heels isn't at all a common sight. Nothing I can do about that, I simply dress the way I like. I spent little over an hour and a half in the store, sipping iced tea and reading reference books on Macs, I was just another shopper, though I like to think I was better dressed than most, including women!

Around 12:30, my stomach was demanding a fill-up, so I left Borders and drove down the road to a strip mall and Subway. By the way, it should be noted that I don't drive in heels, for safety sake, I wear my sneakers while behind the wheel, then change into my heels after I arrive at my destination. Getting out of the car, I headed into the shop which was empty, ordered a six inch meatball sammich which went down real good. My third and final stop of the day was to Best Buy as I love wandering through the place, ogling at all the fancy gee-gaws and other electronics. There was a pretty good crowd and I did get more than a few stares and turned heads here and there, again, I let it pass, even though I did feel the stares at times, a natural reaction I suppose.

And so, my fourth straight jaunt in a skirt and heels went well, no incidents, just the occasional odd stares, nothing more than that, and nothing I haven't anticipated beforehand, given how I was dressed. And with each outing, I felt just a little more comfortable and at ease with myself. If you can't be at ease, then you can't do what I do. PERIOD! However, I still don't feel that I've fully arrived at a total comfort factor to where I literally can go anywhere in a skirt and heels (namely a mall), but I'm not in a hurry, nor am I going to push things, I'll let it all come in its own good time. In the meantime, I have other places to go, and I'm mulling over new places, so I can still have plenty of fun.

[Thighbootguy]

Up the quota by one more... The past three outfits look great!

[radiodave]

Excellent look, as always. You and HappyFeat never cease to amaze. Keep up the great looks!

[danielp6406]

Very nice outfit :-)

It looks like the skirt, shoes and bag are custom made just for you !!!

Many women don't look that good...It's quite amazing how you pull it off so naturally.

(Now that you are wearing a bag, maybe you would like to bring your camera with you ?)

[Bootking]

Jeff, what is truly amazing is that first, you look so natural (especially with the bag) and second, you look DAMN GOOD! Great work, my friend!

[HappyFeat]

I am really trying to dig for a Johnny Cash metaphor, but the best I can come up with is the boy who dresses better than Sue...however you keep walking the line! Lame, I know...

Jeff, that is a fantastic outfit - classy is an adjective that comes to mind. You are really hitting the mark for style and comfort. Its is as if you were born to wear a skirt and heels. Isn't it wonderful to find that comfort zone? You do it so naturally that I will bet that you get more looks because of how you wear it instead of for what you are wearing.

Isn't it funny that when you are comfortable, the clothes somehow just become clothes? Anymore, I really don't pay much attention to those around me when I am freestyling, I just feel so good being free from restriction that nothing seems to bother me. As for any looks that you get, you are right on about people looking because it is not every day they see a guy in a skirt and heels, but I would venture to guess that their second thought is how good you look in them. I'll also bet that when a woman goes out in the same outfit, she gets more looks as well.

You are entering the zone and I am very happy for you!

[JeffB]

TBG, radiodave, Bootking: Thanks for the compliments! I really appreciate the kind words! Guess that means I must be doing something right! HA! But seriously, I've been having so much fun lately, more than I could have possibly anticipated when I began my exploration into skirt wearing, and pairing them with heels only increases the enjoyment factor. It's like I've discovered freestyling all over again, and it's positively intoxicating! I've probably mentioned this before, but it's getting to the point for me where I'll only wear skirts with my heels as pants just don't do it for me anymore. Bottom line: I like how I look in a skirt, I like how I feel in a skirt, and it's an incredible feeling. I consider myself something of a pioneer in the men's fashion freedom movement, and while I don't expect everyone here to follow in my footsteps, but I hope my exploits gives encouragement to those wishing to explore their own freestyling desires. If you have courage and confidence, you can accomplish your fashion freedom goals, regardless of what they might be. danielp6406: Bring a camera? I keep saying that I will, and I keep forgetting as I'm so used to taking the pics before I head out. HappyFeat: Well, keep working on that Johnny Cash metaphor! HA! "Classy" did indeed come to mind regarding the outfit I wore as I always strive to look my best in public. I couldn't agree more with what you said, it does feel like I was born to wear skirts and heels, and I make a point to wear them well, and since that shows outwardly, I guess that's what attracting those random stares. Right now, I can't imagine wearing anything else. And yes, the comfort does indeed build to where what I wear is as normal to me as sloppy jeans and sneakers and I almost forget exactly what I'm wearing until I hear the heels clicking on the sidewalk or floor. Yep, being in that comfort zone is great!

[tallguyinheels]

JeffB - you are always an inspiration. The other day in my much more conservative (no skirt that is), though 5" stiletto heels and longer slacks - walking into a Staples office supply for a lunch errand - A man passed me by in the parking lot at I headed toward the door - I could see his reflection in the glass and he does this big turnaround - to check my footwear out. I immediately thought - "Don't you dare feel self conscience - what would Jeff say." A big smile and didn't thing anything more about my heels during the rest of my noontime errands. You know, I drive a Dodge Ram and don't feel any less safe driving in heels vs. less elevated foot wear. FYI, I think you look great - but my legs could not do a skirt justice.

[scrappycoco]

You know between your self and happyfeet it make's me wish I had more of a selection of heel's and skirt's to wear. Most of the skirt's I wear are jean and I think don't look right with the one pair of heel's that I have. Oh well maybe someday!

[Dawn HH]

JeffB:-) You look natural and fabulous in that outfit. I agree that you look like you always was meant to wear skirts and heels. You certainly have come a long ways since the days that you took pics of your heels in your work cubicle. I enjoyed them then and I equally enjoy your pics of your outfits today. Cheers--- Dawn HH

[rxrenesis]

Nice outfit.

[Mr. X]

Way to go Jeff! I am really digging the Johnny Cash all black thing. I have done it a few times myself. As other have said you look so natural in you attire. It really shows in your pictures. Again, well done!

[Dawn HH]

JeffB:-) Hey, my friend! I think that Happyfeat just put the "Feat" part of his posting name out there, and raised the bar so high that we all will have to wear much higher heels just to reach that spot in heeldom with our fingertips just to even feel like we even belong in that club. What do you think??? Cheers--- Dawn HH

[JeffB]

Dawn HH: I would agree that HappyFeat did indeed set the bar pretty high, but hey, a little competition here and there is bound to make me want to do my very best to present an even better public freestyling image to the public at large. Should prove to be a great deal of fun!

[Dawn HH]

JeffB:-) I'm with you on that and all of the way. Grab that bar. Cheers--- Dawn HH

[Thighbootguy]

JeffB - As DawnHH says "grab the bar", but I suspect it's more like Gary Patterson tells us, "Hang in There" (see image).

[Dawn HH]

It could be a very bumpy ride. Cheers--- Dawn HH

[JeffB]

JeffB -

As DawnHH says "grab the bar", but I suspect it's more like Gary Patterson tells us, "Hang in There" (see image).

HA! That was funny! I like Gary Patterson's golfing pics most! Those are a hoot!

[HappyFeat]

JeffB:-)

Hey, my friend! I think that Happyfeat just put the "Feat" part of his posting name out there, and raised the bar so high that we all will have to wear much higher heels just to reach that spot in heeldom with our fingertips just to even feel like we even belong in that club. What do you think???

Cheers---

Dawn HH

Thank for the praise, however if it weren't for so many of the people posting their outings here I might still be only wearing my heels to get the mail! As for raising the bar, its just about being out there and letting life happen.

I think JeffB would agree no matter the shoes or clothes you wear, you still are the same person and behave in the same way. Instincts are instincts.

Dawn HH: I would agree that HappyFeat did indeed set the bar pretty high, but hey, a little competition here and there is bound to make me want to do my very best to present an even better public freestyling image to the public at large. Should prove to be a great deal of fun!

Well JeffB, a little competition makes us all better. However since there is no real way of keeping score, you just keep getting out and I'll just keep getting out and all of the other guys just keep getting out and we all just keep sharing and then we are ALL winners.

[Dawn HH]

Nicely put, Happyfeat. I'll agree with you on that subject. Cheers--- Dawn HH

[Thighbootguy]

HappyFeat –

Not to dampen the soaring spirit of the competition but you raised a point upon which I differ, “I think JeffB would agree no matter the shoes or clothes you wear, you still are the same person and behave in the same way.” I’m not sure about JeffB but I have learned some stuff from TBG and, TBG has learned some stuff from me. I’ve mentioned that TBG is a persona that I put on along with my boots and that persona is different from plain ole me. TBG is more bold and assertive and has a much thicker skin when it comes to criticism. I, on the other hand, am much less engaging and much better with machines (computers) than people. In the past few years, I have noticed that I have become more outgoing and TBG has fewer sharp corners.

I suspect that many public heelers that don’t wear heel full time also experience a bit of a split personality when they are in heels. After all, if wearing heels wasn’t something “different”, we would wear them all the time.

Then there is the old notion that “Clothes make the man” (substitute shoes for this discussion), and you get the idea that what we wear might change us.

[JeffB]

HappyFeat: Like you, I've learned so much from the people here, and reading their exploits gave me the courage to venture out in heels without fear, followed later by heels AND skirts, my current outfit of choice for my jaunts. Thanks to HHP, I feel that I've grown as a person when it comes to expressing my own brand of fashion freedom, and that's a good thing. And yes, I intend to continue growing, continue pushing the envelope (as in wearing a dress), continue inspiring other heelers to leave their closets and continue having fun! TBG: I don't feel like I become a different personality when I don a skirt and heels, I'm still the same old me, only that I have an eclectic sense of fashion. Nothing more.

[JeffB]

8/15/2009:

After a three week hiatus, due mostly to a combination if crappy weekend weather and general laziness, I was back on the road again as I sported the following outfit for a purely casual Saturday outing:

A blue JC Penney polo shirt, my 22 inch denim skirt, my now favorite short-strap handbag, bare legs and my two inch heeled loafers. Like I said, just casual, nothing fancy, but I longed to wear a skirt and planned to have fun in it. After tapping an ATM, and noticing a couple of turned heads, it was off to a downtown comic shop where I engaged in conversation with the staff and a couple of customers about G.I. Joe which I planned to see, and after that ten minute chat, I was really jazzed to see the flick. After leaving the shop, I walked around the corner to a nearby store for a newspaper, earning a couple more looks, then it was off to South Jersey. First stop was to Chic-fil-A for lunch as I just love their chicken salad sanwiches, especially when paired with a tall cup of lemonade. Yeah! That's livin'!

Then it was off to the Moorestown Mall and the multiplex to see G.I. Joe. Crossing the parking lot to the mall, I pretty much went ignored, even by kids and there were plenty of them there to boot. But I racted casual like any other guy in a skirt on a warm and sunny Saturday afternoon. As for the movie, it was just like the cartoon series from the mid 80's, the perfect sort of slam-bang, high budget, special effects laden, summertime blockbuster, and it lived up to the hype. After the film ended, I decided to take a leisurely stroll in the mall itself, my purpose being to be seen and gauge the reactions, if any. I guess I expected too much because I didn't get any reactions, people simply minded their business and never gave me so much as a serious glance. I must admit I found that to have been slightly perplexing.

From there, it was off to the nearby Barnes & Noble where I spent a solid half hour wandering the aisles, flipping through a couple of magazines and buying some manga before departing for my next and last stop, yep, Best Buy where I spent another solid half hour where it was plenty packed with shoppers, but again, no long looks, extended glances, double takes or anything. I simply went about my business and everyone else went about theirs. Again, it was perplexing since a man in a skirt in a public setting is not a commonplace thing for people to see, and yet, nothing. Still, I did have fun on my outing as I really enjoyed being back in a skirt, wearing it has become as natural to me as breathing, and on a day as hot as this one was, I felt noticeably more comfortable than I would've been in pants of jeans.

There's no longer any nervousness for me when I wear a skirt in public, to me, it's just another piece of clothing, so what if it has only one opening instead of two? Big. Fat. Hairy. Deal. As I've stated many times before, I feel good when in a skirt, and, to be honest, I can't imagine wearing anything else on my freestyling jaunts. I wish I could convey to everyone here just how great it feels to wear a skirt, how delightful an experience it is to me, like I was born to wear this garment that legions of narrowminded people would deny us simply because they believe men shouldn't wear something they believe is the province of women only. Baloney! I'm living proof that men not only CAN wear skirts, but look good in them to boot!

[danielp6406]

Greatings JeffB :-)

Another nice and "casual" outing.

You said "I must admit I found that to have been slightly perplexing"

"Ignored...No reactions...no serious glances..."

You know why ? Many of us said it before and I will say it again:

You look "natural" while wearing your skirt so I guess this is why you don't get any negative reactions.

Congrats

[stefan]

Good for you Jeff, You look really good in that skirt. I totally agree that a skirt is a really confortable garment. And I also beleive, as others, that as long as you look at ease yourself in a skirt not many people will notice. And for some reason a denim skirt seems to go more unnoticed than others. It's almost as its invisible´.

[JeffB]

danielp6406: Thanks for the kind words. Yeah, I suppose I'm just going to have to get used to going relatively ignored while wearing a skirt. HA! But yeah, it does look natural on me, feels natural too! stefan: I quite agree. Denim does seem to go ignored in public. All in all, I guess that can be looked at a good thing.

[JeffB]

8/16/2009:

It's been awhile, but today, I decided to go on a Sunday "Double Skirt" outing.

MORNING

Around 7 a.m., it was off to the supermarket in the following outfit:

A steel blue shirt from Sears, a light, 19 inch khaki skirt from Old Navy, bare legs, my short strap handbag and my two inch heeled loafers. Getting dressed this morning, reaching for a skirt was as second nature to me as putting on a pair of socks. After arriving at the supermarket, I did notice a turned head as I headed inside but kept on going. Being in the market itself was a blase, unrewarding experience as I casually went about my business of buying groceries for the week, for the most part, I had forgotten that I was wearing a skirt, to me, I simply had clothes on, nothing more. But when I got to the frozen food section, I was brutally reminded that I had a skirt on when I felt those way chilly temps on my bare legs. In other words----BBRRRRRR!! Thirty minutes later, I was out the door and on my way back home.

AFTERNOON

After back to back outing in my loafers, I desperately needed some elevation. In other words, it was time for high heels! Here's my outfit:

A forest green polo shirt from JCPenney, my 20 inch black Old Navy skirt, bare legs (of course), my short strap handbag and the Payless Lance Flex pumps in black. Even though I'm mostly all about wearing skirts these days, let me tell you it felt great to be perched again on four inch spike heels and hearing their delightful click-clack cadence on the ground as I strolled towards the Borders bookstore in Springfield on stop one of the outing. And, at the risk of needlessly patting myself on the back, I thought I looked damn good, as I usually do in such an outfit. Heh! Once inside, I picked up the Sunday paper, bought a large iced tea, then relaxed in the lounge area, reading with my legs primly and properly crossed, something I practice that at home. And, as usual, I went pretty much ignored by other shoppers.

Just like this morning, it didn't register to me that I had on a skirt and high heels, to me, it was simply clothes and shoes, nothing more. If I appeared a tad overdressed for the store on an early Sunday afternoon, so be it, I didn't mind, it felt good to be well attired and looking sharp, especially when compared to how sloppily dressed other women were. I mean, it's one thing to be casual, but some of the women I saw went overboard in that regard if you know what I mean. After about an hour in the lounge, I went to check out, bought my paper and left for Subway and lunch. By the time I left, it was already blazing hot, but I didn't feel the heat as I was quite comfortable in the skirt instead of heavy, confining jeans. Once arriving at Subway, I had the place all to myself while I ate, a rarity of sorts, but that was okay.

My third and last stop of the day was at Best Buy, more to be seen than to actually buy anything. I did get a couple of sideways glances here and there, no big deal, I simply went about my business of window shopping, that is, until I stopped at a Wii console and, despite my best intentions, decided to play a game of bowling. So there I was, deeply engrossed in the game, making all sorts of gyrations while rolling the ball and moaning when I couldn't get a strike or pick up a spare. I'm sure I made for quite a hilarious sight, especially in a skirt and heels, but I didn't care, I was having fun. I tell ya, one of these days, I'm gonna buy a Wii for myself! It's awesome! After little over a half hour and with a new DVD in my possession, it was back home after yet another fun filled and rewarding fashion freedom outing.

At this point, I guess I'm no longer perplexed when people ignore me, despite my eclectic choice of clothing. I simply dress the way I like and enjoy the experience. Wearing heels is great, wearing heels and a skirt is fantastic! I simply can't get enough because of how such a combo makes me feel, free, empowered, emboldened. In a way, I'm saying to the world: This is me! This is who I am and how I choose to dress! If you can't handle that, tough! I can't wait to go on another outing!

[stefan]

8/16/2009:

At this point, I guess I'm no longer perplexed when people ignore me, despite my eclectic choice of clothing. I simply dress the way I like and enjoy the experience. Wearing heels is great, wearing heels and a skirt is fantastic! I simply can't get enough because of how such a combo makes me feel, free, empowered, emboldened. In a way, I'm saying to the world: This is me! This is who I am and how I choose to dress! If you can't handle that, tough! I can't wait to go on another outing!

Jeff,

Thoose outfits look great and it feels good that more and more men dresses in skirts and heels. And when they look as hot as you do people should only have a positive reaction.

[ShockQueen]

JeffB, you never cease to amaze. I am so proud of you for going out, having fun, and throwing all caution to the wind. At least in a skirt, you CAN make those wild gyrations trying the Wii Sports games, and someday when you get really good at it, you'll be the most fashionable pro on the Nintendo circuit! :-) I doff my top hat to you, my friend....you are a true class act! :-)