The Jaunts of JeffB!

[SleekHeels]

That's a very comfortable look Jeff, I like the casual look of he denim skirt combined with the smartness of the collared shirt and the sharpness of the shoes, and the bag is a nice touch to complete the outfit. Great combination.

You say casinos are good places to heel because people are usually too engrossed to notice, and I can't help but agree, but do you get so engrossed you forget your wearing heels, a skirt, etc?

[Mr. X]

Nice casual look Jeff! I have not done a casino in heels yet myself. Or a skirt for that matter....lol. It is definitely on my to do list though. The heels I mean...lol. I would love to do Las Vegas in heels. It is definitely on my "high heel bucket list".

[JeffB]

That's a very comfortable look Jeff, I like the casual look of he denim skirt combined with the smartness of the collared shirt and the sharpness of the shoes, and the bag is a nice touch to complete the outfit. Great combination.

You say casinos are good places to heel because people are usually too engrossed to notice, and I can't help but agree, but do you get so engrossed you forget your wearing heels, a skirt, etc?

Oh, yes, I most definitely do! Especially when I'm on a good roll at a slot machine! HA! More often than not, the only thing that reminds me that I'm freestyling is that I always put my handbag in my lap while gambling. Thanks for the compliment on my outfit which I considered to be "low key dressy", the pencil skirt in particular was especially fun to wear. Noticing the attire of other women around me, I was clearly better dressed than say, ninety-eight percent of the women in the casino, even though I was in a casual outfit.

Nice casual look Jeff! I have not done a casino in heels yet myself. Or a skirt for that matter....lol. It is definitely on my to do list though. The heels I mean...lol. I would love to do Las Vegas in heels. It is definitely on my "high heel bucket list".

Great minds think alike! I've also thought about wearing heels while in Las Vegas which I've never visited. That would be a lot of fun to be sure! Heck, I might even pack a skirt or two, maybe a dress and wear them while there. That would be even MORE fun!

[JeffB]

Jaunt #168, 9/8/2012:

Just a short outing today as severe thunderstorms are headed for my neck of the woods later this afternoon, and I prefer to be safe at home when they arrive. Cowardly? You betcha! That's how I roll. Anyhoo, today's brief outing fully solidified my devotion to freestyling as I was super excited to wear a pair of flats in public as I took the Payless "Millie" black patent ballet flats I bought last week out for a spin, pairing them with a navy polo shirt, the 20 inch Old Navy dark denim skirt and a handbag. The Millie flats, in addition to looking really cute, what with the bow in front, they were comfortable as well, and that was a key consideration. So, on my brief trip, I headed first to the city's main post office near downtown to buy a money order, after parking, I hopped out without a thought, put money in the meter and strolled in. There were close to ten people in line ahead of me, but no one paid me any attention as I waited to be served, little over five minutes later, I bought my money order, filled it out and left.

My second stop was a mile away in center city as I swung by my local comic book shop to buy the week's newest offerings. Because it was Saturday, parking was at a premium and wound up little over a block away from the shop, which I didn't at all mind as I got to do some walking in the new shoes. Words can't describe how incredibly liberating it is to wear a nice, comfortable skirt and flats in public, looking as casual and stylish as any other woman taking care of business or just enjoying being out and about on a Saturday, and I was certainly enjoying myself. It's times like these that makes freestyling such an amazing delight, and while I got an odd stare here and there, no one paid me any mind. Of course, the guys at the comic shop treated me as well as ever, despite how I was dressed, I guessed they're used to seeing me in heels and skirts, heck, I'd probably throw them for a loop if I didn't wear those items. Heh! Perhaps I'll do that as an experiement sometime in the future and see what happens. After leaving the shop, I stopped by a convenience store to play the lottery before getting back in the car and heading home.

Like I said, a short outing, but fun since I got to wear a skirt and break in a pair of new shoes. More fun to come!

Edited September 8, 2012 by JeffB

[SkirtDude]

Love the ensemble Jeff! Any more jaunts on the horizon? I thought you'd try a regular pencil skirt, not just a denim one

[JeffB]

Love the ensemble Jeff! Any more jaunts on the horizon? I thought you'd try a regular pencil skirt, not just a denim one

Well, thanks for the kind words. Much appreciated. That denim skirt I bought at Old Navy was really nice and fit me well. I've been busy of late, but I hope to be back on the road for new jaunts soon.

[SkirtDude]

JeffB - are you still around? Not heard from you in a while

[JeffB]

JeffB - are you still around? Not heard from you in a while

Not to worry, my friend, I'm still around. I just haven't had time to go jaunting lately, but I hope to go on a little adventure soon.

[JeffB]

Jaunt #169, 10/13/2012

Hard to believe it's been a month since my last outing! My, how time flies when you're goofing around! HA! Anyhoo, with the weather sunny but chilly (as in temps barely breaking 60), I decided it was time to head out on a jaunt, and for the first time since who knows how long, I wore something other than a skirt----yes, boys and girls, I broke out my thigh high boots! With the weather being rather cool, I figured it was a perfect time to reacquaint myself with the Pleaser Legend 8868's which I paired with my black leather jacket over a gray turtleneck, the Gloria Vanderbilt "Amanda" jeans in dark stonewash, my black faux croc print handbag and a necklace I had bought this past winter. Even though it had been months since I last wore the thigh boots, it didn't take long for me to remember how sleek they looked on me, how they molded themselves to my legs along with the tight jeans to present a fabulous image. Oh, and the sharp, satisfying click of the four inch heels was an added bonus.

My first stop of the day was to the city's main post office near downtown to mail off a couple of parcels, after parking, I hopped right out without any hesitation and walked inside. There had been a lengthy line as some ten people were ahead of me, I would be in line for nearly twenty minutes, but I didn't get much in the way of stares or glances the whole time, but that did get me to wondering what anyone would notice about me first: the tight jeans, the boots or the handbag, neither of which I bother hiding, I'm right out there for all to see, boldly and proudly. Without incident, I finished my business, left the post office, got in my car and headed into town and my favorite comic book shop for the week's newest offerings. Took over thirty minutes of cruising around to find a parking space as it's always crowded downtown on weekends, and the space I finally found was a full block away from the shop, but that was cool as that gave me the opportunity to enjoy a good little walk, just for fun, I put some sway in my hips in my walk, emphasizing my rear end in the tight jeans. That got me a couple of second glances here and there as, when I put my mind to it, I can do a decent strut. Heh!

My time in the comic shop was uneventful as is always the case since the guys there are long used to my unique attire, after returning to my car, I headed into South Jersey where I dined at the Chik-Fil-A near the Moorestown Mall, got more stares there since the place was full of people, young, old and inbetween, but I took it all in stride as I ordered my lunch and ate, spending a good twenty minutes or so in the store. My last stop ofthe day was the nearby Barnes & Noble, a quiet port in the storm of everyday life, and I relished the time I spent there, almost an hour in fact, drinking lemonade while reading sci-fi and sports magazines before I headed to the register with a couple volumes of manga, and it was there that I got a compliment from a twenty-something woman at the register who said that she liked my necklace, and that was after she had seen the jeans, boots and handbag while I waited in line to be served. Go figure! But I smiled and thanked her. Hmm! Perhaps I should wear jewelry more often! HA! All in all, it certainly felt good to get back in the saddle after a month away from jaunting, and I sure had fun wearing heels in public. More fun to come!

[Mr. X]

Looking good as always Jeff! I gotta say. This outfit seems very casual compared to some of the other outfits you have worn.

[bluejay]

Jeff, Another nice outing for you. Your outfit looked great on you! I read that you put some sway in your walk, good for you. Be proud as you walk in your heels. I always do. Since the cool weather is here, I am getting my boots out of their storage totes for future wearings and look forward to boot heeling. By the way, your compliment on the necklace that you received from the woman clerk is a good sign that women like jewelery on men. I wear lots of jewelery and do get complimented often from women. Happy Heeling, bluejay

[JeffB]

Mr. X: Casual? Well, I kinda thought that outfit was dressier than what I had worn previously. bluejay: I will admit I was taken a wee bit taken aback at being complimented on my necklace as I didn't see that coming, but I appreciated the compliment nonetheless. But yeah, jewelry is definitely a component to freestyling that can be most interesting. Meanwhile, while out and about yesterday, I saw scores and scores of girls and women strutting their stuff in tight jeans and leggings tucked into flat and low heeled knee boots. Absolutely delicious! I'm just gonna HAVE to get my hands on a pair of similar boots and follow that particularly fashionable herd!

[Thighbootguy]

JeffB; It is the season for thighboots and you do wear them well Sounds like a fun outing and any complements are nice. If your going after new boots, consider moving up and inch to 8899s. These are my favorite boots.

[tallguyinheels]

My hair stylist (young) says i should embelish with some jewelry now and then - even suggested piercing my ears and danlgling earings for my short grey hair. Hummmm. I'm not sure - my preference is to keeps my conservative, business appearance when out, thhough I doubt a some earings or a necklace would do anything more in response that generate an occasional compliment. Bravo. Notice my Style icon only wears studs.

[Foxyheels]

My hair stylist (young) says i should embelish with some jewelry now and then - even suggested piercing my ears and danlgling earings for my short grey hair. Hummmm. I'm not sure - my preference is to keeps my conservative, business appearance when out, thhough I doubt a some earings or a necklace would do anything more in response that generate an occasional compliment. Bravo.

Notice my Style icon only wears studs.

You can't beat dangling earring and nice necklace, you are right about the lack of reaction you will get though.

[JeffB]

TBG: Well, I still haven't ruled out buying a pair of the 8899's. I might just have them before the year is out. And if I've become adept at looking stylish in thigh high boots, I've learned those lessons from you! Tallguyinheels: Wearing jewelry is pretty cool, makes me wanna hit the stores and see what else I could wear on future jaunts. I still have my strand of pearls, perhaps I'll wear them next and see what happens.

[SleekHeels]

Looking sharp JeffB, the contrast with the light grey turtleneck top really compliments the black boots, jeans and jacket. It's quite cool to wear dark jeans and boots like that, it kind of makes people do a double-take to figure out where the boots end and the jeans start. I agree, accessorizing does add another dimension to outfits that can otherwise look a little plain like something's missing. Just one piece can make all the difference and be really effective at completing a look, just like your necklace did with your latest outfit.

[JeffB]

Thanks for the kind words, SleekHeels! Perhaps I'll wear my black jeans with the thigh boots on a future outing which is an awesome look! In fact, the ONLY thing that'll get me out of a skirt are tight jeans and thigh boots! HA! As I had said previously, it had been pretty cool to have been complimented on that necklace I wore, from here on out, I'll put more work into coordinating the jewelry I wear with my outfits.

[JeffB]

Jaunt #170, 10/20/2012:

Today was a monumental occasion, and I wasn't even aware of it until I got back home. You see, today marked my 100th jaunt in a skirt since I began this thread some four years ago. And, dopey me, I had forgotten that event had drawn close, otherwise, I would've done something fancier, as it was, I did dress up some for today's outing. With temps hovering in the mid to upper 60's with a stiff breeze, despite plenty of sunshine, this was the kind of day that was too chilly for shirt sleeves but not cool enough for a jacket, so I opted for a black mockneck, a brown, 36 inch long Liz Claiborne activewear skirt, the Payless "Tara" knee boots, my black leather handbag and a nice necklace. My choice of outfit was spot on since it was fairly cool yet comfortable, and it felt good to be in that ensemble as well, especially the new skirt which just flowed on me.

My first stop of the day was downtown as I stopped to tap an ATM for some cash, as I waited to cross the street, a guy in a car craned his neck to get a good look at me, actually, a good, LONG look as he held up traffic in his zeal(?) to stare at me, I waved at him, then he drove off. I guess he had never seen a man in a long skirt and heels before. Imagine his reaction if I'd worn a short skirt and shown off my legs! From there, it was off to my local comic book shop for the week's new offerings, but today, I managed to find a parking spot only fifty feet from the front door, bummer! However, after spending a good twenty minutes in the shop, I walked a full block down to a nearby convenience store for a newspaper and to play the Powerball lottery, so I was able to get in a good, long walk so I could bask in the good feelings that came from hearing the heels clicking and the skirt swishing about my calves, and the fun that came from being seen as I did elicit a few second glances here and there.

Then, it was off to South Jersey and to give the crowd at Chick-Fil-A a cheap thrill, and I did just that, earning a goodly number of stares from folks while I waited in line for my order, including what appeared to be a disapproving glare from a mother, her child in tow. Following lunch, it was off to Barnes & Noble for a good half hour of quiet and calm and indifference from other shoppers, reading sci-fi and horror mags in the lounge area before leaving with some manga. My final stop was Best Buy where I got a few more stares while I wandered the aisles and ogling at hi-def TV sets before going to the counter with the Fullmetal Alchemist Brotherhood anime collection. All in all, it was a good outing, and I had fun, even if I did earn a fair number of stares, but that was to be expected as I expressed my freestyling whims.

[bluejay]

JeffB, You had a great day and a great outing in your long skirt and heeled boots. The outfit looked great too. Keep it up! Happy Heeling, bluejay

[JeffB]

Thanks for the kind words, bluejay. I certainly enjoyed myself yesterday.

[roniheels]

Jeff ... What a great and stylish outfit. I always love you wardrobe combinations you put together. You always look so stylish and especially very comfortable wearing them. And don't you just love the "quiet stares" you get from on-lookers? Don't you feel like sometimes you just want to say to them, "...comments?" Great jaunt as always.

[SleekHeels]

The A-line flare of the skirt works well, I think it balances out broad male shoulders very nicely. That's also a fabulous shade of brown - it used to be convention to never wear black and brown together, but with the right shade it looks great and you aced it as usual Jeff.

[JeffB]

Jeff ... What a great and stylish outfit. I always love you wardrobe combinations you put together. You always look so stylish and especially very comfortable wearing them. And don't you just love the "quiet stares" you get from on-lookers? Don't you feel like sometimes you just want to say to them, "...comments?" Great jaunt as always.

Thanks, roniheels! I simply do the very best I can. You have no idea how much time I spend experimenting with top and bottom combinations until I put together something I like. My reasoning for that being if I'm going to wear women's clothes and shoes in public as a male, then I'd DAMN well better look my very best. As for all those "quiet stares", yeah, I do wish I'd get comments! Heh!

The A-line flare of the skirt works well, I think it balances out broad male shoulders very nicely. That's also a fabulous shade of brown - it used to be convention to never wear black and brown together, but with the right shade it looks great and you aced it as usual Jeff.

Thanks, SleekHeels! I appreciate your comments. When it comes to long skirts, I love the A-line style, especially with boots, and as fall continues on and the weather grows cooler, you'll be seeing that combination more and more. Meanwhile, it wasn't too long ago that I disliked wearing brown, but I've come to like the color for it's warmth, and it fits well for this time of the year.

[JeffB]

Jaunt #171, 11/11/2012:

Not that I had been keeping track, it's been almost a month since my last jaunt, so, with the Eagles playing the hated Dallas Cowgirls at 4:30, I figured I had time for an outing, even though the weather was mild, I opted for my faux black leather jacket over a long sleeved, black scoopneck t-shirt, my skin tight stonewash jeans tucked into the Pleaser "Vanity 2013" 4 inch heeled knee boots, a black handbag and, just for fun, a little lipstick. To be honest, there was no real reason, I just felt like wearing it, and, I'll admit it's a cool look and looks good on me. My first stop on this short outing was to the main post office (open on Sunday) to buy a money order, after parking near the facility, I hopped right out, pretty as you please and walked in. There was no line, so I went right up to a window, purchased my money order, filled it out, dropped it off and left, no sweat.

My next stop was across the bridge into South Jersey and Barnes & Noble near the Moorestown Mall. Just llike with the post office, I pulled into the lot, hopped out of the car and strolled right into the store. As was often the case on a Sunday afternoon, the place was pretty well packed, but that didn't deter me as I went about my business, casually wandered the aisles, checking out the latest books (for future download onto my nook™, manga (Japanese comics), magazines and videos. I think I got a couple of stares here and there, but nothing more than that, of course, people DID notice, they just didn't act demonstrative or anything like that. Par for the course with me, I found myself wondering what those people noticed more: the tight jeans, the high heeled boots, the handbag or, in today's instance, the lipstick. I'm sure I probably short circuited a mind or two with my appearance during the thirty plus minutes I spent in the store, call me wicked, but that's rather fun! After waiting in a long line with young kids ahead of me and behind me, I was out the door and on the road back home.

Short as the outing was, it was still enjoyable, as is ANY trip I get to take in high heels. But I think that the spur of the moment added element of the lipstick made today's outing just a bit more exciting, a bit more thrilling, and that increased the freestyling fun quotient considerably! I don't expect anyone here to follow in my long and winding footsteps, it's just what I do, what I love doing!

[ilikekicks]

LOVE the jeans! I soooooo cant wait to get back into mine again! I might have to visit Philly again sometime after winter breaks, care for a Steak-n-Cheese? -Ilk

[Mr. X]

I don't expect anyone here to follow in my long and winding footsteps

Nor should you Jeff! That is what makes this fun! We all love heels, but yet we all seem to put are own little spin on it. I love seeing how each individual person here will either dress up or dress down their heels.

Nice jacket by the way!

[Gudulitooo]

Nice outfit Jeff ! The heels do not look like more than 1 inch (kitten) on your pics ?? Or is it my eye problem not completely finished ? I noticed the lipstick as soon as I opened the pics, and I wondered if it was or only a "stange lips day". After looking for it in your text it proved yes you wore lipstick. Yet I continue to find that it gives you a strange face, a bit like ... Steven Seagal ? I humbly suggest that either you avoid the lipstick, change for a paler color, or you go the full thing with the help of a pro !!

[Thighbootguy]

Jeff; Great look as usual. I really like those boots! I had read you post so I was prepared for the lipstick when I opened the pictures. My eye sees a darker color with your skin but I think Gudulitooo might be on to something here. Why not consult a cosmetics pro? Can't be any worse than trying on heels in a shoe store. Like you keep reminding us, it's all about looking good. Another point, If memory serves, the "hated Dallas Cowgirls" do wear nice boots. TBG

[JeffB]

ilikekicks: Wearing snug jeans is great fun, and with the weather growing cooler, I plan to wear mine more and more! Mr. X: The fun of being part of this community is seeing how others pair their heels with various styles of clothing. As for me, I try to dress up as much as I can. As for the jacket, I bought it at Sears little over a year ago. Gudulitooo: Regarding the boots, the heels are four inchers, I guess the poses from the pictures sort of hide that. As for the lipstick, that was a silly, spur of the moment thing I wanted to do, it never occurred to me that I might look, well, strange. Okay, no biggee, but, Steven Seagal? Really? Wow! TBG: Glad you liked the boots, they're fun to wear. As for your suggestion, perhaps I'll give that a try! Thanks!