JeffB Posted December 15, 2008 Author Share Posted December 15, 2008 Outstanding outing JeffB! Nothing is better than just doing your thing in a natural and relaxed way. The skirts work for you and you wear them well. Just as you posted, even here when the discussion turns to your tops, away from your bottoms, then you prove the rule that a guy in a skirt is no big deal! Like I said, that was my goal, to look as best I could in clothing not normally associated with men while not calling any undue attention to myself by wearing anything flashy or extravagant. All in all, I like to think I succeeded in blending in with my surroundings during my two outings over the weekend as practically no one raised so much as an eyebrow during my jaunts. More importantly, wearing a skirt felt surprisingly easy and natural to me, and that went a long way towards the confidence and casual air I displayed while out and about. I gotta warn you that this is a slippery slope...for me it was women's jeans and pants and now I have basically two wardrobes! However many of the pants I wear on a regular non-outing basis, but removing gender form clothing can get very expensive! Of that I have no doubt, but then, what isn't expensive these days? HA! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Bubba136 Posted December 15, 2008 Share Posted December 15, 2008 Bubba, your dissemination of my outfit was outstanding! Thank you very much for your unintentional cooperation My cooperation wasn't in any way unintentional. ROLMAO Being mentally comfortable in your own mind is the key to wearing heels in public. Link to comment Share on other sites More sharing options...
HappyFeat Posted December 16, 2008 Share Posted December 16, 2008 More importantly, wearing a skirt felt surprisingly easy and natural to me, and that went a long way towards the confidence and casual air I displayed while out and about. Of that I have no doubt, but then, what isn't expensive these days? HA! Well, the natural feeling of wearing skirt and heels with confidence and casual air is priceless! Style is built from the ground up! Link to comment Share on other sites More sharing options...
JeffB Posted December 16, 2008 Author Share Posted December 16, 2008 Well, the natural feeling of wearing skirt and heels with confidence and casual air is priceless! Priceless indeed, my friend! Having confidence when it comes to something like this is not just key, but essential! If you're not comfortable in your own skin, whether it's wearing just heels, or heels and a skirt, then you'll never be able to pull it off successfully. You have to grab the bull by the horns and tell yourself you have every right to go wherever you want, dressed however you want----within reason of course! If you want to wear women shoes or a skirt, then that's YOUR choice and your choice alone! Never allow society to dictate how you choose to live your life! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Thighbootguy Posted December 16, 2008 Share Posted December 16, 2008 JeffB - Sorry I missed the first round of comments. I thought the first sweater (even though it is “of my faves”) was a little busy for the rest of the outfit. I like the second one much better but there is still a proportion that (to my eye) isn’t quite right. I think it’s the hem of the sweater being below the waist of the skirt. It is hiding the higher waist line which I think would bring the look into a better proportion. The sweater inside the waste of the skirt probably won’t work and would look a little odd. Tech and I have been known to disagree but I think he may be right on this one, “try a shirt”. You might try your boots with the 5” heels to also change the proportion a bit. And, with a skirt that long you could wear any length boots. As for the outings... bravo, confidence strikes again. One caveat though, The guys in the comic book store are in a world of their own and I don’t think they would have noticed what you were wearing unless you went in as Wonder Woman (that is not a suggestion). You mentioned, “After back to back outings, wearing a skirt in public became as natural to me as breathing, and that amazed me.” Please take my 101 year old aunt’s advice, “Quality work takes time.” I won’t go into my complacency nagging because I’m sure already one step ahead of me. TBG I dream of a world where chickens can cross roads without having their motives questioned. Link to comment Share on other sites More sharing options...
Bootking Posted December 17, 2008 Share Posted December 17, 2008 but there is still a proportion that (to my eye) isn’t quite right. I think it’s the hem of the sweater being below the waist of the skirt. It is hiding the higher waist line which I think would bring the look into a better proportion. I couldn't put my finger on it - but there it is! Jeff, try a plain sweater under the skirt! It's all about the heel! Link to comment Share on other sites More sharing options...
JeffB Posted December 17, 2008 Author Share Posted December 17, 2008 JeffB - Sorry I missed the first round of comments. I thought the first sweater (even though it is “of my faves”) was a little busy for the rest of the outfit. I like the second one much better but there is still a proportion that (to my eye) isn’t quite right. I think it’s the hem of the sweater being below the waist of the skirt. It is hiding the higher waist line which I think would bring the look into a better proportion. The sweater inside the waste of the skirt probably won’t work and would look a little odd. Tech and I have been known to disagree but I think he may be right on this one, “try a shirt”. "Busy", huh? Well, you do have a point there regarding the first sweater, however, it helps keep me warm, and that's what I was going for in particular that day as comfort trumped fashion. Heh! As for future outings, I'll give one of my turtlenecks a try! You might try your boots with the 5” heels to also change the proportion a bit. And, with a skirt that long you could wear any length boots. Of late, I haven't gone over four inches as a prefer shorter lengths for comfort on long outings which often include a goodly amount of walking, and the "Tara" boots are VERY comfortable to wear for long periods. As for the outings... bravo, confidence strikes again. One caveat though, The guys in the comic book store are in a world of their own and I don’t think they would have noticed what you were wearing unless you went in as Wonder Woman (that is not a suggestion). Not to worry there! I'm not into the cosplay thing anyway! HA! You mentioned, “After back to back outings, wearing a skirt in public became as natural to me as breathing, and that amazed me.” Please take my 101 year old aunt’s advice, “Quality work takes time.” I won’t go into my complacency nagging because I’m sure already one step ahead of me. Okay, I'll be careful of complacency, still, it had all been so easy, and so much fun! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
JeffB Posted December 20, 2008 Author Share Posted December 20, 2008 12/20/2008: You call this "the jaunt that wasn't". My plan for today was to go on a third straight outing in a skirt and heels. The weather was crisp and chilly but nothing I couldn't handle. After putting together my outfit (Black leather jacket over black turtleneck, the long denim skirt I wore last Saturday and the Pleaser Vanity-2013 boots) I went downstairs and was ready to leave when, all of a sudden, I experienced what I could only describe as a feeling of malaise. In simpler terms, out of nowhere, I just didn't feel like going out in that outfit. One minute I was eager to hit the streets in my skirt and heels, and the next, I couldn't bring myself to bother, so, I didn't. I went back upstairs, changed into my sloppy, rumpled male clothes and went out. Hell, I didn't even drive, I took public transit downtown and goofed around for a few hours. The thing is, I didn't miss not taking advantage of the opportunity to enjoy an outing. Upon further review, I suspect I didn't want to drive and deal with all the chaos on the roads as shoppers descend on malls, my favorite hangout for outings in humongous droves to take care of their last minute holiday shopping. Well, that's it for this jaunt that wasn't. But it was no big deal, I just thought I'd share today's unique and unexpected turn of events. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
secondtake20 Posted December 20, 2008 Share Posted December 20, 2008 JeffB We all have those day's. Don't worry about it you will be back at it after the hoildays are over. Link to comment Share on other sites More sharing options...
my6heels Posted December 20, 2008 Share Posted December 20, 2008 Jeff, the same happened to me last Wednesday and I stay at home but ... I went out on Thursday with my red pupms in a beatiful stroll troughout the BArcelona streets.... There are days and days, ever to go out with heels!!! No big deal. Link to comment Share on other sites More sharing options...
Dawn HH Posted December 21, 2008 Share Posted December 21, 2008 JeffB:-) We all get days like that sometimes. I'm off on the weekends and sometimes I don't even feel like getting out of my jammies and spend all day in them with Mickey. Sometimes you feel like a nut, sometimes you don't. Sometimes you just feel like you have to put on a pair of heels and lounge around all day. Right now I have to stay out of heels for a few more months until my back finishes healing itself up, but that time will come again. Cheers--- Dawn HH High Heeled Boots Forever! Link to comment Share on other sites More sharing options...
JeffB Posted December 21, 2008 Author Share Posted December 21, 2008 It was rather remarkable what happened yesterday. Nine times out of ten when I decide to go out on an outing, it's a done deal. Oh, well, like I already said, no big deal. There's always next time! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Thighbootguy Posted December 21, 2008 Share Posted December 21, 2008 I lose the desire to go out every once in a while. Sometimes it lasts for a few days other times it lasts for a week or so. Some might observe that in those periods I have come out of my own world and joined the real one, but I’ll let folks that care what world I’m in argue that point. Stopping for a while, however, does give me the opportunity to reevaluate what I’m doing. I found that when I do start going out again, going out is less of a big deal each time I go through the cycle, it become more natural and easier after each period of retrospect. I dream of a world where chickens can cross roads without having their motives questioned. Link to comment Share on other sites More sharing options...
JeffB Posted December 29, 2008 Author Share Posted December 29, 2008 12/29/2008: I was back in the saddle today, going on what a call a "three-pronged" outing, and here's my outfit: My favorite black leather jacket over a blue turtleneck, the long denim skirt from three weeks ago, black L'eggs tights and the Pleaser Vanity-2013 boots. Not to sound boastful, but I thought this made for a nice outfit, especially with how the sweater and skirt matched, just like the jacket and boots matched. I strive and work as hard as I can to be properly color coordinated. As for the three-pronged outing, my first stop was to the post office little over a mile from home to buy a money order to pay a bill. The main lobby was quiet and there were only three people ahead of me in line, my wait wasn't too long, just over five minutes, and while two people got in line behind me, no one paid me much, if anything in the way of attention. After buying my money order then going over to a desk to fill it out, I did get a frown and a long stare from an older black gentleman checking his box but didn't sya anything as I took care of my business then left. Stop number two was at Pizza Hut for lunch. I was seated little over five feet away from a two women and four kids, none of them older than six or so in their care, one of the kids, a girl grinned and waved at me and I waved back, nothing from the other kids or the women. Regarding the former, I half expected them to shout out: "Mommy! That man's wearing a skirt!" at the top of their little lungs, but that never happened. Fortunately. Otherwise, everything was calm and quiet, while I did get a double take from a couple of diners, No one made a big deal of my attire. In hindsight, going to Pizza Hut might have been a mistake because I opted for the lunchtime buffet and ate more than I should have. Urgh! Did I ever feel stuffed after I finished. Stop number three was a couple of miles away to one of my favorite haunts, Borders bookstore. Even though it was a weekday after Christmas, the lot was surprisingly crowded as it took a few minutes to find a parking space. Walking to the store, I got a double take and long stare from a black guy in a car, but that was it, once inside which was pretty much packed, I was just another shopper browsing the aisles for manga and/or magazines I was interested in, I ordered a tall iced tea from the in-store cafe and relaxed in the lounge area for well over half an hour with a couple of sports mags I read while sipping my tea, legs crossed femininely the whole time while no one gave me so much as the time of day. Needless to say, it was an enjoyable experience. It should be noted that this was my third straight outing in heels and a skirt, and while I was on my way back home, I suddenly found myself wondering if just wearing heels is enough for me anymore. Sure, it would've been simpler to have just worn slacks or jeans with the boots, but I was eager to wear a skirt again because I had so much fun in my last two outings, and I've come to love the skirt I wore today as I enjoyed feeling the denim swishing about my legs as I walked. All in all, it was very thrilling, pushing the envelope yet again in my exploits of fashion freedom. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
HappyFeat Posted December 29, 2008 Share Posted December 29, 2008 Quite an exciting outing, mainly because it was rather uneventful- just a relaxing outing in your boots and skirt. It is inspiring to know that a guy can just do as he pleases and blend in. I like the outfit and it is very well put together. You are most certainly inspiring me! Maybe its time you match it with those killer merlot pumps... I was back in the saddle today, going on what a call a "three-pronged" outing... I like this tactic- not just for heeling but for spending a day out. Too often, when I go out for the afternoon (which is more and more often in heels) I kind of rush through things and don't slow down to enjoy what I am doing. If I may "borrow" the "three-pronged approach" it could lead to more satisfying heeling. It should be noted that this was my third straight outing in heels and a skirt, and while I was on my way back home, I suddenly found myself wondering if just wearing heels is enough for me anymore. Sure, it would've been simpler to have just worn slacks or jeans with the boots, but I was eager to wear a skirt again because I had so much fun in my last two outings, and I've come to love the skirt I wore today as I enjoyed feeling the denim swishing about my legs as I walked. All in all, it was very thrilling, pushing the envelope yet again in my exploits of fashion freedom. Though I have yet to wear a skirt to more traditional public places, I can identify with this. I have worn heels out with men's clothing for years, but recently discovered women's jeans and slacks, which I almost exclusively wear with heels now (as well as with men's shoes). They are more comfortable, fit me a bit better and the styles are simply more exciting. From there I even got nail color are wore sandals. This I may or may not make a habit, but seizing the opportunity to be free of gender based fasion restrictions is thrilling in and of itself. While I was out at a club recently- the kind of place where a guy in a skirt doesn't really merit too much curiosity- in my red skirt and peep toe pumps, I too thought I could get very used to working skirts into my regular rotation. I love your outings, JeffB! They really get me thinking and pushing me to new heights! Style is built from the ground up! Link to comment Share on other sites More sharing options...
latindancer Posted December 30, 2008 Share Posted December 30, 2008 Hey JeffB, Skirt again!!!! heheehe, glad your enjoying yourself. Keep it up. Great outing. LD Link to comment Share on other sites More sharing options...
Bootking Posted December 30, 2008 Share Posted December 30, 2008 Jeff, what could possibly be next???? It's all about the heel! Link to comment Share on other sites More sharing options...
latindancer Posted December 30, 2008 Share Posted December 30, 2008 Maybe a shorter skirt!!!! LOL Latindancer Link to comment Share on other sites More sharing options...
rxrenesis Posted December 30, 2008 Share Posted December 30, 2008 Bravo Jeff If the shoe fits BUY IT http://s10.photobucket.com/albums/a145/rxrenesis/Shoe%20Shots/ Link to comment Share on other sites More sharing options...
JeffB Posted December 30, 2008 Author Share Posted December 30, 2008 Quite an exciting outing, mainly because it was rather uneventful- just a relaxing outing in your boots and skirt. It is inspiring to know that a guy can just do as he pleases and blend in. I like the outfit and it is very well put together. You are most certainly inspiring me! Maybe its time you match it with those killer merlot pumps... Funny you should mention that. I've been working on clothing combinations to pair with the merlot pumps. The next step for me down the road will be wearing a skirt and pumps, so why not those? I like this tactic- not just for heeling but for spending a day out. Too often, when I go out for the afternoon (which is more and more often in heels) I kind of rush through things and don't slow down to enjoy what I am doing. If I may "borrow" the "three-pronged approach" it could lead to more satisfying heeling. By all means, help yourself. I do try to plan my outings in advance so I don't waste precious time or gas driving from one place to another, deciding on the fly where I'm going on my outings. Rushing through things is no fun, take time and enjoy yourself more. Though I have yet to wear a skirt to more traditional public places, I can identify with this. I have worn heels out with men's clothing for years, but recently discovered women's jeans and slacks, which I almost exclusively wear with heels now (as well as with men's shoes). They are more comfortable, fit me a bit better and the styles are simply more exciting. From there I even got nail color are wore sandals. This I may or may not make a habit, but seizing the opportunity to be free of gender based fasion restrictions is thrilling in and of itself. I agree fully. While I've yet in invest in women's pants and/or jeans, I'm thinking about doing so just for my outings. While I was out at a club recently- the kind of place where a guy in a skirt doesn't really merit too much curiosity- in my red skirt and peep toe pumps, I too thought I could get very used to working skirts into my regular rotation. I love your outings, JeffB! They really get me thinking and pushing me to new heights! Glad to hear that. Since I'm not a night person, wearing skirts in the daytime has proven to be no big deal to me so far, and I hope to be to continue exploring this aspect of my fashion freedom in the future. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
johnieheel Posted December 30, 2008 Share Posted December 30, 2008 No wander I don't get any attention. There is too much compitition out there with men wearing skirts AND heels! Hmmm... Since I don't wear skirts, maby I should try going out in my red mj's or step up the beet and tuck my pants into my boots. real men wear heels Link to comment Share on other sites More sharing options...
latindancer Posted December 31, 2008 Share Posted December 31, 2008 hahahahaha.....LOL Link to comment Share on other sites More sharing options...
Dawn HH Posted January 1, 2009 Share Posted January 1, 2009 Johnieheel:-) Why not? A little competition never hurt anybody. Try it---you may like it. Cheers--- Dawn HH High Heeled Boots Forever! Link to comment Share on other sites More sharing options...
JeffB Posted January 4, 2009 Author Share Posted January 4, 2009 Maybe a shorter skirt!!!! LOL Latindancer Maybe later! Right now, it's too damn cold out! HA! I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Dawn HH Posted January 4, 2009 Share Posted January 4, 2009 JeffB:-) Right you are. Longer skirts for now and shorter skirts for warmer weather when the warm air will feel good through your pantyhose onto your legs. Soon it will be time to show those legs off. Big props to you my man. Cheers--- Dawn HH High Heeled Boots Forever! Link to comment Share on other sites More sharing options...
JeffB Posted January 8, 2009 Author Share Posted January 8, 2009 1/8/2009: And now, my first outing of 2009! YAY! In addition to that, this was my fourth straight outing in heels and a skirt. Regarding the latter, there was nothing else I thought about going out in. Here's pics of today's outfit: My black leather jacket plus a navy turtleneck, L'eggs black tights (to help offset the winter chill), my now favorite long denim skirt and the Payless "Tara" boots. Like I said, this was my fourth straight outing in a skirt, and I've become more and more comfortable wearing it. Now, I won't go so far as to say I'll only wear skirts with my heels from now on, but I love having options to dress pants and jeans. As for today's outing, it was rather busy as I made five stops. The first was to a downtown ATM for some cash, it was quite blustery, so walking the half block to the ATM, it was cool (pardon the pun) to feel the wind whipping the skirt about my legs as I walked. Whether or not anyone paid me any attention, I didn't care, I simply went about my business, got my money, walked back to my car and drove to my favorite comic book shop for this week's newest offerings. No problem there either as I was in the store for a good twenty minutes, chatted with a couple of shoppers, neither of whom paid any attention to my attire. Stop number three was to Arby's in the western 'burbs for lunch, had to wait a bit as there were three people ahead of me, no problemo. I think an older lady who was ahead of me in line gave me a long stare after she got her order, but I was sure, nor did I care. I took my time eating my food while reading the sports section of the paper, just a leisurely lunch where I was treated like just another customer. Nothing more, nothing less. Confidence was, as usual, high, I felt comfortable and at ease, in my mind, it was no big deal to have been out in a skirt, and I tailored my attitude towards that mindset, something I always seek to do. Stop number four was to Borders to see what was new in the manga aisles, grabbed a couple of books plus a couple of magazines then went to the lounge area where I proceeded to leisurely read my materials, I think I was in the store for well over half and hour reading, sitting next to a couple of Gen Xers who, for the most part, paid me no mind, oh sure, they glanced my way from time to time, but that was it. After paying for my purchases, I was off to my final stop of the day: Best Buy. To me, I was pushing the envelope by going into the uber-popular big box store in a skirt, but I just didn't care, I was feeling bold and felt like showing off. As is my wont, I spent a lengthy period of time in the store, browsing the anime and Blu-Ray aisles, gawking at HD TV's (even though I have one) and playing a couple of games of bowling on a Wii console. Sadly, I didn't do well, the first game I rolled all of a 93, 136 in the second. Urgh! But I had fun and was really involved in the game, not caring if anyone noticed the tall, African-American man in heels and a skirt gesturing and gyrating with every roll of the ball. I think I spent nearly an hour in the store as I often do when I'm in Best Buy, my unofficial "second home", but like everywhere else, I was treated like every other customer. From there, it was back home. Like I said, I'm growing increasingly more comfortable doing public outings in a skirt, almost to the point where the heels have become secondary, and I've pushed the envelope just a little further by wandering through a big box store in one. Perhaps sometime down the road, I don't know when, I'll wear a skirt into a mall. That figures to be the ultimate push. Stay tuned. I don't want to LOOK like a woman, I just want to DRESS like a woman! Link to comment Share on other sites More sharing options...
Dawn HH Posted January 8, 2009 Share Posted January 8, 2009 JeffB:-) Great outing for you, my friend. Your progress is astounding. And you look good in a skirt. Keep us posted on your next step in public heeling. Cheers--- Dawn HH High Heeled Boots Forever! Link to comment Share on other sites More sharing options...
danielp6406 Posted January 9, 2009 Share Posted January 9, 2009 JeffB :-) Another great adventure for sure. (For me, it won't be soon I will wear a skirt in public...) Next time, bring your camera with you and take more pictures ! Happy heeling ! Link to comment Share on other sites More sharing options...
HappyFeat Posted January 9, 2009 Share Posted January 9, 2009 Great outing JeffB! I was wondering when you were going to get out and about again in your skirt. In fact, I had planned to spend the day heeling and was strongly considering wearing a skirt, but due to a long line of snafus the day wound up being scrubbed. Besides, being the wimp I am, it was so cold and the longest skirt I own is just below the knee, I probably would have passed anyway. Kudos for the skirt on a day like today! I am impressed at your casualness about doing what you choose. The fact that you didn't even consider wearing anything other than what you did gets major props from me. Also, the activities you engaged in were quite visible and not even caring to notice other's reactions shows that you are truly a skirt guy! Now if the Eagles do as well as you this weekend! Style is built from the ground up! Link to comment Share on other sites More sharing options...
Bootking Posted January 9, 2009 Share Posted January 9, 2009 But I had fun and was really involved in the game, not caring if anyone noticed the tall, African-American man in heels and a skirt gesturing and gyrating with every roll of the ball. Come, come now! Never mind the heels and skirt!! But GYRATING in the store, for shame, for shame........ LOL It's all about the heel! Link to comment Share on other sites More sharing options...
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