The Jaunts of JeffB!

[bluejay]

Very nice look, JeffB. I like the royal blue color of your top. Great color combination. Makes your outfit pop. Glad to see your matching bag, with your shoes. I'm carrying a bag more and more these days, myself. Happy Heeling, bluejay

[JeffB]

Many thanks, bluejay! In the beginning, I was a tad self-conscious about carrying a handbag, today, I don't go anywhere without one.

[Foxyheels]

As always Jeff you continue to be an inspiration and a pioneer for us to follow, love that skirt it's the perfect length and fit.

[SkirtDude]

Many thanks! I certainly liked that outfit, and I felt good wearing it too! And yes, I will have to see about wearing more pencil skirts in the future as they really suit me.

Finally you're coming round to my way of thinking, JeffB! regular pencil skirts (non-denim) look great on guys, I found this pic on the web... http://picasaweb.google.com/lh/photo/rb0jOCvCT9QAdL_v1g9HTkFrP4p_S7rH1Je70NeqrK4?feat=embedwebsite teamed with the right heels and even a polo top, it's a look you could demonstrate to us one day... I like this look http://1.bp.blogspot.com/-92jdlgnOWhw/UTXiRnx4UgI/AAAAAAAAFgc/9NUFveEmJFQ/s1600/girl+in+animal+print+shirt+pencil+skirt+tights+blue+pumps.jpg but I'll add my own touch to it.. push the envelope and show us a real pencil skirt soon

[JeffB]

Finally you're coming round to my way of thinking, JeffB! regular pencil skirts (non-denim) look great on guys, I found this pic on the web... http://picasaweb.google.com/lh/photo/rb0jOCvCT9QAdL_v1g9HTkFrP4p_S7rH1Je70NeqrK4?feat=embedwebsite teamed with the right heels and even a polo top, it's a look you could demonstrate to us one day... I like this look http://1.bp.blogspot.com/-92jdlgnOWhw/UTXiRnx4UgI/AAAAAAAAFgc/9NUFveEmJFQ/s1600/girl+in+animal+print+shirt+pencil+skirt+tights+blue+pumps.jpg but I'll add my own touch to it.. push the envelope and show us a real pencil skirt soon

Well, you'll be happy to know that I've been window shopping online for a proper non-denim pencil skirt similar to the first picture, and yes, I have no doubt I can dress one up nicely with the right top (perhaps a silk or satin blouse) and a pair of stiletto pumps. As for the second picture, I'm not sure I could emulate that stunning jacket, but I think I could come up with something just as sharp. Going all in with wearing skirts has opened new vistas for me as a freestyler, and I'm eager to see where that road goes.

[SkirtDude]

I love the second pic and am looking for a sexy, tight skirt like that one... the only awkward issue I have with regular pencil skirts as opposed to denim is what kind of underwear would help control my... er anatomy. I want that smooth look to the front of the garment, when I wear a denim skirt it is no issue due to tougher material. Could you give me some pointers pls? Conversely I ordered a denim pencil skirt off eBay, instead of the usual fare ...

[JeffB]

I love the second pic and am looking for a sexy, tight skirt like that one... the only awkward issue I have with regular pencil skirts as opposed to denim is what kind of underwear would help control my... er anatomy. I want that smooth look to the front of the garment, when I wear a denim skirt it is no issue due to tougher material. Could you give me some pointers pls?

I wear a one piece body briefer which helps considerably when it comes to presenting a smooth frontal profile while keeping the babymaker from being prominent, heck, it even gives me quite a nice looking derriere which comes in handy when wearing tight skirts. Of course, the degree of success you might have with a briefer depends upon how well....endowed you are. You might have to experiment to find something that will work best for you.

[SkirtDude]

Thanks for the advice.. I was looking at a pic of mine in a beige skirt and think I need to hide the salami... I dont want VPL so aside from a half slip I dont know what would help... aside from trying to squeeze into a size 6 (UK ... tummy control panties are quite pricey and the Mrs has only just gotten used to me in pencil skirts though she wants me to wear darker colored ones like black, gray, navy... (skirts btw not underwear....) I also wear kilts (hence the name) of the same kinda shades...

I will upload a pic of the beige one for your opinion... http://www.hhplace.org/uploads/gallery/album_319/gallery_15255_319_82636.jpg

[Steve63130]

Kilty, Nice skirt but the "male equipment" still shows rather prominently on that photo. Try something like this. It might help. You need to learn to tuck the gear back and out of the way. http://www.glieberman.com/a313-abs-sense-shaper-boxer-briefs/ Steve

[SkirtDude]

Thanks, I ordered a tummy control slip, and some briefs, its one size smaller than my regular skirt size, and hope that goes toward making stuff less visible. Also that beige skirt's material is quite flimsy, its not as tight on my hips and thighs as I'd like so more likely for stuff to show. I just want to dress as a guy like JeffB, but keep it casual. The kilts need no explanation, I have a denim kilt I wear, and black denim pencil skirt along with a smarter black pencil skirt that I wear to work on dress down Fridays that I can team with a polo shirt and flats like our trend-setter JeffB... I am getting my colleagues used to me in the kilts before slipping in a regular skirt or two Still looking for a nice set of boots to complete the look, with some nice heels

[JeffB]

Steve63130: I've tried tucking, and didn't like it because it wasn't at all comfortable, thus my decision to go with a briefer. Kilty: The problem, per se with wearing knit pencil skirts is that they can be quite clingy, showing off every little thing, including, for us guys, our packages which again makes wearing a briefer a must. Now, I wear denim a lot since the places I often go call for more casual attire, though I've dressed up a time or two when going to a restaurant. Since I've embraced the philosophy of fashion freestyling, it's all about the total outfit, the shoes are simply part of the overall equation, not the be all and end all, thus my wearing flats of late.

[SkirtDude]

^{JeffB, thanks for the advice. It's not the easiest of subjects to discuss but thanks for the advice. I have ordered some tummy control briefs, that will help. Stronger material skirts / kilts also help. I find lighter colors make things worse, so I'm sticking to grays blacks navy when it comes to pencil skirts, and the type of material. I want to wear them as a guy, I don't want to 'pass' as a woman. I think the limited fashion choice for men has to change, even some of the rappers are realizing its time to dress how they really feel... http://rumorfix.com/...omens-clothing/ though sadly there is a backlash and 'followers' are calling it 'faggotry' and other more unmentionable things... they said the same about skinny jeans, and look, all the sheep are wearing those now, so I'm sure it will be the same with skirts... if that link didn't work, google 'Trinidad James', he's the latest to embrace the skirt along with A$AP Rocky Kilts are nice, but damned expensive compared to a skirt}

[JeffB]

Kilty: I forgot to mention how lighter colors could help expose more than you intend, which is while I wear a goodly amount of darker colors myself. The link you provided worked just fine, most interesting indeed. As for the backlash, it's just more of the same old tired nonsense about how people with prehistoric mindsets continue to equate clothing with sexual preference. It's easy for these idiots to call men who choose to wear skirts gay, but NEVER proclaim that women who wear pants or jeans are dykes. Can you say "double standard", boys and girls? It's so irritating. Meanwhile, is a kilt more expensive than say, a leather skirt? Heh!

[SkirtDude]

Kilty: I forgot to mention how lighter colors could help expose more than you intend, which is while I wear a goodly amount of darker colors myself. The link you provided worked just fine, most interesting indeed. As for the backlash, it's just more of the same old tired nonsense about how people with prehistoric mindsets continue to equate clothing with sexual preference. It's easy for these idiots to call men who choose to wear skirts gay, but NEVER proclaim that women who wear pants or jeans are dykes. Can you say "double standard", boys and girls? It's so irritating. Meanwhile, is a kilt more expensive than say, a leather skirt? Heh!

JeffB, most of the briefs I ordered was black, so I should be okay... I'm not taking chances with white.. I will try that beige skirt with the control slip and briefs and see if that makes any difference. I don't want to hide the fact I'm a man, I just love the comfort and variety of skirts as well as kilts. What with more of the 'Hip Hop set' embracing skirts, hopefully the sheep will settle down and not make these stupid statements. I got my black denim skirt today, and am loving it the Mrs is in two minds and fears before long I won't wear anything 'male' anymore... She's not convinced it's a 'pleatless utility kilt'... Kilt prices are too high, and the fact I can pick up a pencil skirt for a fraction of the price is madness. I am learning to tune out from the backlash, and I won't be surprised to see myself in a 'Man Skirt' tweet with photo anytime soon... looking forward to your jaunt in a cute (non-denim) number Thanks for the advice Jeff

[JeffB]

Kilty: By all means, let me know what happens with the brief and how it works with that beige skirt. I agree wholeheartedly with what you said about skirts being comfortable, especially on hot, humid summer days, I feel so much cooler, even moreso than when wearing men's shorts. I've mentioned this more than once, but I almost never wear men's shorts beyond my front porch or to a store around the corner because I don't feel at ease in them, not even knee length cargo shorts, but I've worn skirts as short as 15 inches everywhere without a care in the world. As for a jaunt in a knit pencil skirt, that will be coming soon.

[SkirtDude]

Kilty: By all means, let me know what happens with the brief and how it works with that beige skirt. I agree wholeheartedly with what you said about skirts being comfortable, especially on hot, humid summer days, I feel so much cooler, even moreso than when wearing men's shorts. I've mentioned this more than once, but I almost never wear men's shorts beyond my front porch or to a store around the corner because I don't feel at ease in them, not even knee length cargo shorts, but I've worn skirts as short as 15 inches everywhere without a care in the world. As for a jaunt in a knit pencil skirt, that will be coming soon.

Jeff, I got my briefs and control slip today, but I ordered the wrong size I'm at least a size 12 in these, the 8 shipped is too difficult to move in (let alone pull up quick enough when nature calls) so I'll save it for cold winter days... it can stretch to knee length but that made me shuffle around like Kim Kardashian so I wear it at the length you see in the pics...

wheras the briefs kept my cargo.... er... secure

I feel so self conscious in that beige skirt now (and its a magnet for dirt, smh) that I don't wear it out much...

but I've got a nice grey one

You'll have to show us your new pencil skirt and tell us of your latest jaunt....

that shows what a good job the underwear now does... I didn't realise so much is needed for this Fashion Freedom carry on

[Shafted]

Modesty is almost always the key to good taste. Like the gray skirt on you. Nice piece.

[JeffB]

Kilty: Well done! The briefs certainly did make a BIG difference with that gray skirt you displayed. Pair that with a red blouse and a pair of black pumps and you'll look supremely stylish. To fully explore the joys of fashion freedom does require a bit of a financial commitment, but if you're careful and spend wisely, you can pull it off. Keep on keeping on!

[SkirtDude]

(blushes) Thanks so much for the kind words, Shafted and JeffB... ...

hey just a little disclaimer (I won't delete the pics) but the control slip had some sort of "bottom uplift" panelling on it which made it look like I've got granny panties on as well as being too hard to move around in if worn at knee length. Unless I'm wearing it wrong, I was surprised it was so tight even for a size 8 I can at a push fit into a size 8 skirt though I'm usually a 10 (heading to 12 and need to diet), and in regular jeans a 34. I went on my first real long public outing to a large out of town shopping centre (Lakeside) yesterday, wearing my cardigan teamed with a short navy pencil skirt, though I wore different shoes... I tried pop sox and trainers, like what a girl would wear to the office before popping on her heels... I was aiming for a casual look,though I think the look may have backfired... I felt very exposed and the skirt rode up a little, and I had to keep pulling it down every so often

though sceptical at first I know proper underwear does make a difference and makes things look a lot more presentable than before. I didn't bother with a slip on such a warm day. My heart was pounding as I left the car and went inside the mall - a group of teenagers passed me, looked, but said nothing. I walked around for 20 minutes or so, went to an ATM to take some money out, but had to answer the call of nature. I need advice from skirted members here as I felt a bit out of my comfort zone. Had I been in a kilt, I would have walked into the men's, but this time I went in the disabled toilet at McDonalds after ordering a takeaway... It's the whole skirt up panties down sit and pee stuff I'm still adjusting to (sorry for the graphic picture, but I can't think of the best way to explain)... In a kilt I don't feel as worried as kilts although uncommon are seen as just smart menswear... do most of you guys when skirted just say to hell with it and use the men's and find a stall? I just was very anxious. I bottled out of buying a dress in one shop, was worried about asking to try it on as I didn't want to upset any ladies using the changing rooms (it was busy), though the sales assistant, despite the confused look on her face was very helpful. I think I'll stick to eBay for now... Once back home, I was glad I pushed myself out there, but I'll never have the same confidence as JeffB does, or some of our more experienced members...

Does this anxiety subside after a while? Oh, and one other thing - is there a short window of time which after a while we cannot edit posts or amend them? I tried to amend something recently and couldn't. Jeff, sorry for hijacking your thread, I just thought I'd share my first jaunt if I may use the word, with you

[JeffB]

Kilty: No big deal, you could always start your own thread about your outings! Nice pic by the way, but wasn't it hot wearing a cardigan at this time of year? On the subject of answering nature's call, I make sure to visit the bathroom before leaving home, and, when out and about and I have lunch somewhere, I'm careful about how much I drink. There was one time when I did have to go while at a multiplex a few years ago while wearing a skirt, I just went in the men's room, did my business, washed my hands and left, easy as that. As for buying clothes, I don't bother with changing rooms, I know my size and buy whatever I like and try it on when I get back home, but I leave the tags on and keep the receipt handy, if something I buy doesn't fit or doesn't look right, I simply return it, however, that's yet to happen. As for anxiety, don't feel bad about it or let it get to you, it happens to all of us from time to time, even me. Yes, anxiety does fade away eventually, but don't force it away, it's all about the process of developing your "emotional armor" that helps you freestyle with confidence. Just keep at it, that confidence will come.

[SkirtDude]

_{Okay, I get the hint, you don't want me around anymore (runs out of room sobbing) I may start my own thread, though it won't be as good as yours... BTW I did wear that cardigan as it was a lot cooler yesterday... it was raining too, but I was indoors for most of my trip to the mall}

[tallguyinheels]

Kilty and Jeff, Just as the Tallguy - looking good in pencil skirts - all business like. I've picked up a few more and as fall approaches I'll do more skirting the evelope.

[JeffB]

_{Okay, I get the hint, you don't want me around anymore (runs out of room sobbing) I may start my own thread, though it won't be as good as yours... BTW I did wear that cardigan as it was a lot cooler yesterday... it was raining too, but I was indoors for most of my trip to the mall}

I'm sure you'll do we'll with your own thread, don't worry about how good it might be, just express yourself as best you can and describe the joy you experience from wearing the shoes and clothes that you love, nothing more, nothing less. By the by, that was a nice cardigan, I might have to investigate one myself.

Kilty and Jeff, Just as the Tallguy - looking good in pencil skirts - all business like. I've picked up a few more and as fall approaches I'll do more skirting the evelope.

I've been thinking that one has to effect a professional look when wearing a pencil skirt, especially when you add a dressy blouse, hosiery and a sharp looking pair of pumps. The idea is to look elegant, really put together in that sort of outfit, and I'm eager to see what I can do with that.

[SkirtDude]

Jeff, don't bother with wool-knit versions of the pencil skirt, they stretch out and lose shape... regular tailored ones look good, with a decent split at the back for movement Looking forward to your next jaunt, I'll get off your thread now

[JeffB]

Thanks for the tip, Kilty! I'll certainly keep that in mind. Speaking of jaunts:

Jaunt #197, 8/24/2013:

Yesterday was an anniversary of sorts. It was around this time five years ago that I first wore a skirt in public which you can read about HERE. The denim skirt I wore in late August of 2008 I wore yesterday which I paired with a black polo shirt, the Payless "Cori" wedge flats and a black handbag. Regarding the skirt, the brand in question is Canyon River Blues and I bought it at Sears, and after all these years, it remains my go to skirt which I've worn more than any other in my collection, I've worn it in spring, summer, fall and winter and with flats, pumps and boots. It's hard to explain, but it always feels good to wear this skirt and it continues to look good on me. I just LOVE to wear it!

As for my outing, it was sunny, breezy and delightful and I couldn't wait to hit the road. My first stop was downtown and my favorite comic book shop where I chatted with the staff about the recent casting of Ben Affleck as the new Batman. We all found that curious, and a wee bit comical. After leaving the shop, I walked up a block to a convienence store to buy Saturday night's Powerball ticket (didn't win), then went on an unexpected stroll around the neighborhood looking for a store to buy a newspaper, I covered a good half square mile in my search, walking at a slow, casual pace so I could be seen, but no one paid me any mind as I strolled about until I finally found a paper at a CVS drug store. It felt great to walk about in a crowded downtown area and have no one gape or gawk or giggle or give me a wide eyed stare at what I wore. I was just an ordinary, middle aged man in a tasteful skirt, nothing more.

Back in my car, I was off to South Jersey and headed to the Moorestown Mall area where I went to Chick-Fil-A for lunch, after parking, I hopped out and strolled in the store, pretty as you please. There was a decent crowd in the store, but again, no one paid me any attention as I bought my lunch and ate. From there, it was off to the nearby Barnes & Noble where I spent well over half an hour reading a few magazines in the lounge area with a glass of lemonade before going to the check out with a couple of manga volumes. No big deal at all. As usual, I felt perfectly at ease and comfortable wearing a skirt, and again, I can't think of one good reason to go back to wearing jeans. Meanwhile, I just ordered a very pretty two piece dress from Sears this morning for my upcoming 200th jaunt. Stay tuned....

[Mr. X]

Looking good as usual Jeff! And not alot of people can say they are wearing the same clothes they wore 5 years ago! Let alone look good doing so! Well done!

[JeffB]

Looking good as usual Jeff! And not alot of people can say they are wearing the same clothes they wore 5 years ago! Let alone look good doing so! Well done!

Well, other than that skirt, a pair of brown faux croc ankle boots from Payless and a pair of two inch heeled loafers bought via mail order, I don't have anything else in my wardrobe that's five years old. And thanks for the compliment! Much appreciated!

[SleekHeels]

As always you project an image of someone who's totally comfortable with what they're wearing, but even approaching your 200th jaunt you've kept that sense of excitement too. Maintaining that balance is mighty impressive Jeff.

[Curt]

Hi jeff, thanks for inspiring others here to dress the way they like and feel comfortable. I probably never have worn tall boots over jeans if it wasn't from reading your thread, now I wear them every day. Keep up the good work.

[JeffB]

As always you project an image of someone who's totally comfortable with what they're wearing, but even approaching your 200th jaunt you've kept that sense of excitement too. Maintaining that balance is mighty impressive Jeff.

Thanks for the kind words, my friend. I think that things really took off for me when I added skirts to the equation, opening a whole new world to me when it comes to fashion. I suspect that if I had stayed with just jeans and heels, I would've gotten bored, but wearing skirts have indeed made things MUCH more exciting to me, and it opened new horizons in terms of footwear choices as I came to appreciate flats which are fun to wear. My evolution from heel wearer to fashion freestyler has been rewarding, and more is to come!

Hi jeff, thanks for inspiring others here to dress the way they like and feel comfortable. I probably never have worn tall boots over jeans if it wasn't from reading your thread, now I wear them every day. Keep up the good work.

Well, I'm glad to have inspired you and opened your eyes about new and different fashion choices. I hope you'll continue to evolve and develop your style.