The Jaunts of JeffB!

[SF]

???????? (wow)....

[JeffB]

JeffB,

You certainly had a great heeling jaunt today. Your look was really nice. The long skirt kept your legs warm too, for a winter's day. Glad you enjoyed yourself out and about.

Happy Heeling,

bluejay

Thanks for the kind words. Actually, it wasn't too terribly cold yesterday as temps reached into the low 50's, so it wound up being a comfortable day. Still, I was eager to wear that nice looking skirt which I found to have been rather stylish.

Jeff: Just a thought, but having regard to your ethnic background, I wonder if some people might assume you were going for some sort of 'tribal African' look by wearing a skirt etc (if not heels)? (I might have put that a bit clumsily but I think you know what I mean.) After all, long 'skirt-like' garments are by no means unknown on men in many cultures and long boots (heels or not) are also sometimes worn. Would a white man in the same outfit be considered more 'unusual' and comment-worthy, or not?

Hmm! Now that's a most interesting question, and something that never occurred to me before. To be honest, I'm not entirely sure my attire could be considered as "African Tribal" since I wore purely "Western" style garb, still, that was a very intriguing premise you suggested. And yes, I have seen men of different cultures wearing skirt like garments, though with typically boring men's shoes instead of stylish heels. As for whether or not Caucasian men would be considered unusual, I'm not sure, especially since I've rarely gotten comments on my attire. I suppose it all depends on the people such a man would interact with.

???????? (wow)....

C'mon now, is that all you have to say?

[Curt]

JeffB, I like how you call you outings. A jaunt! A jaunt is basically a walk in the park. You dress the way you want and bring inspiration to the others who want to do it. I've broken down a lot of barriers from reading your posts. Are your jaunts everyday? I usually wear some type of high heel every day and try to be on the cutting edge of fashion! Keep your jaunts coming! Clar

[JeffB]

JeffB, I like how you call you outings. A jaunt! A jaunt is basically a walk in the park. You dress the way you want and bring inspiration to the others who want to do it. I've broken down a lot of barriers from reading your posts.

Are your jaunts everyday? I usually wear some type of high heel every day and try to be on the cutting edge of fashion!

Well, I'm glad my exploits have inspired you. Guess that means I'm doing something right. Heh!

To answer your question, my outings are on weekends as I don't have the time during the workweek to go out.

[Curt]

Cool! Wearing heels is an everyday thing for me. I'm to the point where I don't go out for the sole purpose just to show off my heels. I just wear what I like. Going to church is different. I wear a different outfit every sunday. I dress to impress. Sort of like a runway model in an everyday life sort of thing.

[HappyinHeels]

JeffB, Glad to see you're taking freestyling to new venues as promised in 2013. I have never worn a skirt to a dealership but have worn women's jeans with wedge sandals and kneeboots a couple of times. Boots garnered no meaningful attention while the wedge sandals got compliments from several girls also wearing wedges. The world seems to thrive on praise and confidence. HappyinHeels

[JeffB]

Cool! Wearing heels is an everyday thing for me. I'm to the point where I don't go out for the sole purpose just to show off my heels. I just wear what I like.

Going to church is different. I wear a different outfit every sunday. I dress to impress. Sort of like a runway model in an everyday life sort of thing.

Sounds interesting. What sort of outfits have you worn to church?

JeffB, Glad to see you're taking freestyling to new venues as promised in 2013. I have never worn a skirt to a dealership but have worn women's jeans with wedge sandals and kneeboots a couple of times. Boots garnered no meaningful attention while the wedge sandals got compliments from several girls also wearing wedges. The world seems to thrive on praise and confidence. HappyinHeels

Well, I'm trying to broaden my horizons by going to new places in heels/women's clothes, something I find to be an exciting concept that I'm sure to enjoy. And yeah, it's always good to get compliments on what we wear.

[Curt]

JeffB, I've worn all my 4.5" pumps and knee boots to church, and my 3" high heel boots when my legs are sore. I also wear fitted womens leather coats, one is from the 70s, that had the patchwork of colours, sort of what superfly would have worn in '72. I've worn flare jeans, skinny jeans, the the tight flare dress pants that all the cool girls wear. I get all the looks, but never any comments on my heels, but they say I look 20 years younger than I really am. its probably from being skinny, dyed blonde hair, and too much make-up! Ill have to update my gallery. I'm trendy, but not quite as fearless as you! My look is sort of like a cross between lenny kravitz and cheryl crow. Tight flare pants, cool coats, and killer heels. Keep us updated on your jaunts!

[Stilletto2004]

Wow, what a great story Jeff! You continue to inspire me.

[JeffB]

JeffB, I've worn all my 4.5" pumps and knee boots to church, and my 3" high heel boots when my legs are sore. I also wear fitted womens leather coats, one is from the 70s, that had the patchwork of colours, sort of what superfly would have worn in '72. I've worn flare jeans, skinny jeans, the the tight flare dress pants that all the cool girls wear. I get all the looks, but never any comments on my heels, but they say I look 20 years younger than I really am. its probably from being skinny, dyed blonde hair, and too much make-up!

Ill have to update my gallery. I'm trendy, but not quite as fearless as you! My look is sort of like a cross between lenny kravitz and cheryl crow. Tight flare pants, cool coats, and killer heels.

Keep us updated on your jaunts!

What? No skirts or dresses? If I were the religious type, I'd definitely be inclined to wear a skirt or a dress, especially the latter to church. To be honest, I wouldn't wear anything else! But hey, to each their own, and it sounds like you do wear some interesting outfits! Good for you, my friend!

Wow, what a great story Jeff! You continue to inspire me.

Well, I'm glad to have done so. That makes everything I've done here by relating my adventures worthwhile. By all means, keep on reading!

[Curt]

No skirts or dresses. But never say never! I love the long tight pants and the pumps. I've got a few pics of me in a leather miniskirt with stockings and pumps. The stockings are so sheer that you can see all the tattoos on my legs. Ill send you some pics soon. Btw, my skirt is a size 0. I wish I had the curves you have!

[JeffB]

No skirts or dresses. But never say never! I love the long tight pants and the pumps. I've got a few pics of me in a leather miniskirt with stockings and pumps. The stockings are so sheer that you can see all the tattoos on my legs. Ill send you some pics soon. Btw, my skirt is a size 0. I wish I had the curves you have!

Curves? Me? Nahhhhh! Not quite! Don't tell anyone, but I use a body briefer which gives me the sort of profile for wearing skirts and tight jeans. It also emphasizes my butt which is pretty cool! In fact, I keep waiting to hear someone mutter about me while on a jaunt, "Damn! He's sure got a nice ass!" HA! Meanwhile, I wear a size 14, so I envy you. If I were to stop being lazy and lose some weight, wearing a 12, perhaps a 10 would be a breeze.

[SleekHeels]

That's a fairly light shade of grey which, given the shape of the skirt and the contrast with the rest of the outfit in black, makes for a bold statement. The bag is a really nice touch too, it kind of looks like something's missing when it's not there. Do you find that you get less reactions wearing a total outfit compared to a more conventional guy look with heels? That certainly seems to be what I've found to be the case.

[JeffB]

That's a fairly light shade of grey which, given the shape of the skirt and the contrast with the rest of the outfit in black, makes for a bold statement. The bag is a really nice touch too, it kind of looks like something's missing when it's not there.

I know. I've said this before, but I actually don't feel dressed and won't leave the house unless I have a handbag. And, it's fun to carry one too! I guess that appeals to my feminine side. Heh! As for the outfit, you have a good eye, my friend, I was actively seeking that level of contrast when I put it together. I've said this before too, but I go to great lengths to look my very best when wearing women's clothes in public.

Do you find that you get less reactions wearing a total outfit compared to a more conventional guy look with heels? That certainly seems to be what I've found to be the case.

Hmm! That's a darn good question. To be honest, I never gave that much thought before now, but I think you're onto something there. I often wonder why I don't get much in the way of reactions, positive or negative when out and about, especially when I'm wearing a skirt. Perhaps the juxtaposition of a guy wearing traditional guy clothes with just heels is somewhat jarring to the eye and is likely to draw more attention than a freestyler like myself who opts for the full package. I make no bones of the fact that I dress like a woman, so maybe my appearance makes people think that I'm not trying to hide anything or attract attention like a conventional heeler would. I could be totally wrong, but that's my opinion. What do you think?

[ilikekicks]

I make no bones of the fact that I dress like a woman, so maybe my appearance makes people think that I'm not trying to hide anything or attract attention like a conventional heeler would. I could be totally wrong, but that's my opinion. What do you think?

Man.. you have it all wrong! Its all those damn women trying to impersonate and compete with our very own JeffB! The cock on them to defy the gods and do such a blasphemous thing!

Being serious though.. Ive found that when I was wearing those harem pants, the doctors visits in skirts and a ' full ' outfit, things go a lot smoother.

Recently, I have been wearing the long-backed shirt, some form of leggings and boots of various types and nobody really gives me a second look that I have noticed. When I was wearing my flannel hoodies and regular mens jeans, I do recall a few non appraising looks from both men and women alike.

Blah! Its all good

-Ilk

[JeffB]

Isn't it unusual, the things people notice, or don't notice? I guess it all depends on the attitude and mindset of the people we encounter when out and about. It'll be interesting to see how much attention I get the next time I wear a dress. That ought to be entertaining.

[SleekHeels]

Jeff I agree with you, the "juxtaposition" does seem to shake things up a bit. I hadn't considered the "not trying to hide anything or attract attention" aspects because I don't try to do either when I wear my heels (although it's nice to exchange smiles or even compliments when it happens). But in general you're right, I think people would show their reactions more towards discovering concealed heels or seeing more extravagant outfits.

With a more self-assured feminine outfit it seems easier for people to mistakenly think we want to be women, put us in that category and be politically correct about it. So while I enjoy a more feminine outfit with my heels some days, on other days I prefer a more masculine outfit (that's still women's jeans and a shirt) with my heels because it feels less misunderstood and more like a statement that's being perceived true to who I am.

[JeffB]

Jeff I agree with you, the "juxtaposition" does seem to shake things up a bit. I hadn't considered the "not trying to hide anything or attract attention" aspects because I don't try to do either when I wear my heels (although it's nice to exchange smiles or even compliments when it happens). But in general you're right, I think people would show their reactions more towards discovering concealed heels or seeing more extravagant outfits.

Well, I don't hide anything in regards to what I wear while out in public. I don't go out of my way to wear anything extravagant, I simply wear what women wear, nothing more, nothing less. Because I'm a man wearing skirts and heels shouldn't factor into the equation, but it does because of that ancient mindset that equates clothing with gender and is difficult for most to break, even in this so-called enlightened age. Still, I'm amazed I don't get more reactions, given what I wear.

With a more self-assured feminine outfit it seems easier for people to mistakenly think we want to be women, put us in that category and be politically correct about it. So while I enjoy a more feminine outfit with my heels some days, on other days I prefer a more masculine outfit (that's still women's jeans and a shirt) with my heels because it feels less misunderstood and more like a statement that's being perceived true to who I am.

How ironic that when women wear flannel shirts and baggy jeans, people don't mistakenly think they want to be men, so the double standard when it's the other way around makes no sense whatsoever. When I go out, I'm making a statement that I'm comfortable enough in my own skin to wear what I like, even though it's from the women's side of the aisle, that I'm proud to wear women's clothes, I feel good in them and I look good in them, so why not wear what makes me feel good? That's what women do, so why should they have all the fun?

[BobHH]

There are two kinds of clothes (and shoes): 1) The clearly feminine styles aimed at women by the fashion industry and the sexy/stripper type suppliers. 2) Everything else. Women can choose from all of the above, but men are stigmatized if they choose 1). Since many feminine styles are intended to reveal/enhance the female's body to attract the male, no wonder a male who wears them might be seen as gay by many.

[Steve63130]

Bob, not to hijack this thread, but the folly in that argument is that what makes the female attractive to men (especially item 1) isn't necessarily what makes a man attractive to a gay man. But people don't see that. They jump to the erroneous conclusion that if he's dressing as a woman, he's trying to attract a man. Illogical when you analyze it. Steve

[JeffB]

I would agree that is an incorrect assumption. Some eight years ago, I worked with a gay man, nicest guy I had ever been around, not to mention a rabid fan of Philly sports teams, and he once told me that he hated stereotypes about gay men, that they're flamboyant and wore women's clothing, he said that nothing was further from the truth. In my case, I wear the clothes because I like to, not because I'm on the prowl for men or trying to attract them, that's silly. Of course, to the uninformed, they no doubt have that erroneous opinion, and, more often than not, nothing can shake them of that belief.

[LuvyourShoes]

I agree Jeff. I know many gay men and ALL of them wear masculine things with a small hint of feminine accessories. Alot of them dress like the "average" guy. People and their assumptions... smh

[HappyinHeels]

Something struck me reading all thes posts that I had never considered before which may explain why so many, men and women, have misconceptions about gay men. They are among the most productive and creative people on Earth. Designers of fashion the world over, designers of all the fabulous heels we love, the world's best hairdressers, chefs, artists, etc. are dominated by gay men and some women and so many of them are so misunderstood. They tend to be much more affluent than the average heterosexual man because they are so involved and I think this fuels the fires of mystery. There will always be intrigue and outright jealousy by those inside a certain box toward those outside of a certain box. When I think back through all the relationships I have had, from friends to neighbors, family members, and extended family members, I can think of two whom I trusted implicitly. Implicitly for me means such; If in some emergency I needed to retrieve three things from my safe, and I am thousands of miles away, I could give these two people the safe combination and they would retrieve only those items, peer at nothing else, and secure those items for me without asking why I needed them because these peple have demonstrated LOYALTY to me and this is something of a lost virtue. Both these individuals are gay, one a female musician in Vancouver and the other a gay man in Flagstaff, AZ. I have discovered a person's sexual orientation , while a big thing to others, completely dissappears behind the overwhelming sense of trust these people have earned because of their ETHICS. A person, whom you trust implicitly, does not have to ask why something is done or why you ask since they already know you will tell them in due time. People fear what they don't understand or what they perceive they may be in competition with for reasons known only to them. We cannot control what other people think but we can help guide the conversation away from mistrust and toward understanding. HappyinHeels

[Bubba136]

Most people have to earn mistrust and I seriously don,t believe sexual orientation has much, if anything, to do with with it.

[JeffB]

At the end of the day, it's just clothes, nothing more, nothing less. Why people insist upon assigning gender labels or sexual orientation on clothing is a mystery to me. Damn stupid as well. Just as women are allowed to wear jeans and hiking boots without facing reprecussions, men should be allowed to wear skirts and heels and be given the same level of public acceptance. Yeah, yeah, I know that's a naive viewpoint, but that's what I believe.

[ilikekicks]

I would agree that is an incorrect assumption. Some eight years ago, I worked with a gay man, nicest guy I had ever been around, not to mention a rabid fan of Philly sports teams, and he once told me that he hated stereotypes about gay men, that they're flamboyant and wore women's clothing, he said that nothing was further from the truth. In my case, I wear the clothes because I like to, not because I'm on the prowl for men or trying to attract them, that's silly. Of course, to the uninformed, they no doubt have that erroneous opinion, and, more often than not, nothing can shake them of that belief.

I dont mean to hijack your jaunt, but I would like to express a ' finding ' and my view on it.

When reading posts, I sometimes often reflect on whom I am posting to. Granted, Im very rough around the edges and somewhat staunch in my ways ( yes, Im an ass! ), but there are many things Im outright ' neutral ' on.

Until I read your last post, I didnt know if you were gay, straight, bisexual..

Whats not odd.. I didnt know nor did I care.

At the end of the day, it's just clothes, nothing more, nothing less. Why people insist upon assigning gender labels or sexual orientation on clothing is a mystery to me. Damn stupid as well. Just as women are allowed to wear jeans and hiking boots without facing reprecussions, men should be allowed to wear skirts and heels and be given the same level of public acceptance. Yeah, yeah, I know that's a naive viewpoint, but that's what I believe.

I still have no idea why people must equate clothing to genders. Your viewpoint is not naive, but probably more common then you or I might know about. Its very rare that I am harassed for what I wear. You go to an even higher level of freestyle then I do and I dont really recall you ever posting anything very condescending in the reviews that you have received while out on your jaunts.

Cheers!

-Ilk

[JeffB]

I dont mean to hijack your jaunt, but I would like to express a ' finding ' and my view on it.

When reading posts, I sometimes often reflect on whom I am posting to. Granted, Im very rough around the edges and somewhat staunch in my ways ( yes, Im an ass! ), but there are many things Im outright ' neutral ' on.

Until I read your last post, I didnt know if you were gay, straight, bisexual..

Whats not odd.. I didnt know nor did I care.

Well, that's certainly good to know. And, for the record, I am straight.

I still have no idea why people must equate clothing to genders. Your viewpoint is not naive, but probably more common then you or I might know about. Its very rare that I am harassed for what I wear. You go to an even higher level of freestyle then I do and I dont really recall you ever posting anything very condescending in the reviews that you have received while out on your jaunts.

Other than a giggle or chuckle or a pointed index finger here and there (and even that's been rare), I haven't been harassed either, not even when I've gone out in a miniskirt and heels. Fancy that. I recently joked in another thread that I'm too imposing a figure for people to make fun of when dressed in women's clothes, but I attribute the lack of attention, be it positive or negative to being ignored by the public as they're too wrapped up in their own lives and affairs to bother with me. That's my story and I'm sticking to it!

And now to get things back on track with a new jaunt....

Jaunt #179, 2/24/2013:

After a soggy and overcast Saturday, I decided to hit the road for a little outing before settling in to watch the Phillies playing spring training baseball against Detroit. Yes, spring training baseball. I know, I know, I'm a sports junkie, a month from now when the NCAA men's basketball tournament (a.k.a. March Madness) kicks off, you won't hear from me at all!

Meanwhile, I hit the road in my chocolate brown faux leather jacket over a black mockneck, a 39 inch brown knit skirt (similar to the gray skirt I wore in Jaunt #178, also bought at Sears), a matching woven belt, the Pleaser 2013 Vanity knee boots and a dark brown handbag. As I've said before, I feel perfect at ease and comfortable in a skirt as I do in heels, the funny thing is that it took a wee bit longer to establish that comfort factor with carrying a handbag, and, as I've also said way too many times, now, I don't leave the house without a purse. But I digress, I headed west into Springfield and Best Buy as I was looking for a video adapter for my laptop, after arriving, I hopped right out and headed inside, the store was fairly well populated at little after 11:30 a.m. and practically no one paid me any attention, no gasps, no long stares, no giggles, titters or chuckles or pointed fingers, I walked up to a salesperson, told him what I looked for and he took me right to the area where I found the gadget I sought. After nearly thirty minutes of happy wandering, I went to the register, paid for my item and left, simple as that.

Now, I'm not going to say I've become jaded about my freestyling and the fact people don't give me so much as the time of day, I still wish for people to come up to me with questions or comments, either positive or negative about my attire, if but for no other reason than to chat about what I wear and I why I wear it. I'm sure that would result in good conversation, perhaps I might even be able to enlighten or open a closed mind about freestyling and why men choose to wear women's clothes and/or footwear. I do feel a measure of disappointment when said opportunities fail to present themselves, as was the case today. Oh, well, there's always next time.

[Mr. X]

Love reading your stuff Jeff. I am not personally a fan of long skirts on a man or a women! But that is besides my point! I like reading your stuff! You are one of many around here helping our cause with your constant stream of pics and posts about your jaunts. Thank you! And happy heeling!

[JeffB]

Mr. X: Well, I can't expect everyone to like what I wear, but that's cool! I appreciate your honesty. I'm also appreciate your comments about my little adventures, and I'm glad to be helping the cause in my own unique way.

[bluejay]

JeffB, Everyone has their likes and dislikes in fashions and heels. That's why there is such a variety out there for us to choose from. I too, like your sense of fashion style, so keep on posting! BTW, that's a nice looking ensemble that you wore out on your last jaunt. Happy Heeling, bluejay