Doing New York City---IN A SKIRT!!

[JeffB]

On Sunday, I did perhaps THE craziest thing ever to date, but I did it anyway: I went on a trip to New York, and I wore a skirt on my trip!

I had already planned to go there last week, but after my first little outing in a skirt on Thursday, I got a wild and maybe insane idea on Saturday to repeat the experience, but on a much larger scale by visiting the nexus of western civilization for a day of fun and frolic. Just in case anyone thinks I'm pulling the collective legs of the membership, here's proof of my incredible outing:

As for my wild crazy itinerary:

With my train scheduled to leave Philly at 9:25 a.m., I arrived at a nearby parking lot about thirty minutes before, it took a good ten minutes to screw up my courage, after all, this time, I wouldn't be tiptoeing through a local strip mall or skulking to a ATM machine, I'd be far away from home, far removed from the comfort level of my hometown, I'd be walking the streets of Manhattan in a skirt, and that caused me to have some second thoughts, especially with my jeans and sneakers in the back seat, but then I said, "Screw it! Let's go!" And I did.

Casually walking into 30th Street Station, my first stop was to an ATM for some spending money, then it was off to wait for the train. For anyone unfamiliar with 30th Street Station, Philly's hub for Amtrak and our regional rail lines, the inside is a huge, cavernous, block long building filled with hundreds of travelers of all ages going here, there and everwhere, and there I was in my skirt, acting surprisingly calm, cool and collected. However, my senses were on full alert as my eyes scanned the people around me and (this will be a theme), no one paid me any attention. That helped to build up my confidence for the trip.

After boarding the train, there was no turning back, I was off for the big city. After arriving around 11 a.m., maintaining my casual air, I strolled through the passenger area of Penn Central Station, ten times more crowded than Philly, again, no one noticed. Walking outside, I took a deep breath and smiled at how well things were progressing before heading off to goof off. I've been in Manhattan dozens of times as I wander to NYC every other month or so to sightsee and shop, but being here in a skirt made the experience feel brand new, like I had never been here before, and it was positively exhilirating to me.

Needless to say, it was amazing, wandering through midtown Manhattan in broad daylight in a skirt, and, near as I can tell (and I checked for reactions behind mirrored sunglasses), no one noticed, no one craned their heads, no one did double takes. Of course, we are talking New York, home to perhaps the most jaded populace on the planet, so I guess I wasn't anything in the way of an oddity to the locals. Hey, that was fine by me. After browsing through a comic shop for the newest books on the shelves, followed by lunch, it was off to Bryant Park where I sat amongst hundreds and hundreds of people, enjoying the sights and sounds like everyone else.

After almost an hour there where I was on display for passersby, I was off for Rockafeller Plaza and the "Top of the Rock", the city's famous observation deck seventy floors up where the view of the city was fabulous, and where I had that picture taken. Again, no one cared what I wore, in fact, on a couple of occasions, I had people ask me to take their picture. After leaving the Rock, it was back to the station for the trip back, walking leisurely down a crowded Fifth Avenue where I patiently waited with hundreds of travelers waiting for their trains. Again, nothing. By about seven p.m., I was back home and my adventure was over.

All told, I spent nearly ten hours in skirt, half those hours in one of the busiest cities on Earth, and I was just another person on the street, nothing more. The whole trip went off without a hitch from start to finish, and that pleasantly surprised me. In retrospect, I wish I had worn a shorter skirt, but I didn't want to push the envelope on my first ever really big outing. Now that I've gotten the lay of the land, I will wear a shorter skirt on my next trip. All told, the experience was more fun than I could have possibly imagined. Already, I can't wait to do it again!

[shyguy]

Great outing, I wouldn't know but I'm guessing that in more crowded busy blaces people have less time to notice anybody else for any reason. As has been said though, you just look "right" in a skirt, and with your confident air no one would notice anything wrong as they aren't being drawn to look at you by your manner. Again well done, and enjoy yourself.

[at9]

Sounds like a great day out. New Yorkers have seen it all before. Even more than Londoners. I recognised the location of the picture before reading the text. "Top of the rock" is a good alternative to the Empire State Building. Two advantages. You get a great view of the Empire State Building. You can pre-book timed tickets so you don't have to queue.

[Trinity]

That sounds like a great trip JeffB, your confidence is certainly sky high. Planning on going in a shorter skirt is testament to that. Well done and glad you had a great day

[Bubba136]

What a great adventure! The only way I can think of that it could have been better is having a Pastrami on Rye and a pint of beer for lunch at one of NYC's famous Kosher Deli's and a chance meeting with kneehighs. (which shoes did you wear? The loafers?)

[JeffB]

Thanks for the compliments, everyone! Yeah, my confidence is certainly sky high after my impromptu adventure on Sunday. I had envisioned all sorts of less than pleasant scenarios during my time in New York, the fact that I covered so much ground with incident was quite a relief to me, and that made the experience all the more fun for me. shyguy: Quite right, the fact that New York is so busy made my being out and about all the easier. I appreciate what you said, saying I "look right" in a skirt. And you know what? I do! Not only did I look right, I felt right too, wearing a skirt was as natural to me as breathing, and I'm loving that. Bubba136: Well, for me, I would've had soda with that pastrami and rye, but yeah, lunching with kneehighs would've been fun. Heh! Oh, yeah, I forgot to mention that I did wear the loafers with my outfit. I'm a nut for walking when I'm in New York and probably covered a good three to four miles on Sunday, maybe more. Doing all that walking in heels would've been suicidal!

[Bootking]

Well done, Jeff, well done!

[maninkirt]

Sorry JeffB I haven´t had time doing my posting sending my congratulations to you and your great outing in New York City, I had a busy day yesterday, thats why. No JeffB it wasn´t an insane idea going to New York City dressed in your new skirt. IT WAS JUST A GREAT IDEA, JeffB. A bit wild but a great idea. You did just great. When I hear you talking about New York City, you know I would very muck like to go there too. It seemes to be such a fantastic city. I can see you spent nearly ten hours in skirt. Guess you felt very good about it. Your confidance growing all the time, Guess you beginning feeling comfortable wearing a skirt, hope I´m right. I can see you wishing you had worn a shorter skirt. Thats great JeffB! There you see, you confidance wearing skirt, a shorter skirt is coming. Its great JeffB! You planning wearing a shorter on your next trip, well thats fantastic JeffB. Good Luck! I can realy recomend you wearing a shorter skirt. Was out together with my boyfreind Sunday to a race meeting. I was wearing a short denim skirt (14 inch long, from waist to hem line), I was feeling real good in this short skirt. Feeling free. My legs looks perfectly well, I don´t have to feel ashamed about my legs and together with a pair of sheer lycra nude pantyhose my legs looked great. The rest of my outfit, if you´re interested was a white tight roundeed scooped neck top with short sleeves, a white low buttoned cardigan and my new white trench. I´m sure you too soon will have the confidance wearing a shorter skirt. It looks good (my boyfreind tells me I do), I feel free and its a bit of a challange too, a bit daring. Bet you had your new handbag with you on your trip. I had mine. Mine a bit the same as yours, the same size. I always have a bigger handbag when we´re out like this for a whole day, my boyfreind and me. Its good having a bit bigger handbag. I can have all my things in there as well as for example, some fruits (you have to eat, haven´t you), a bottle of minral water, thing like that. Guess you´re a bit like me. I never go out witout my handbag. Yes a handbag is just a great invention for people like you and me. I had rather been together with you doing the New York City than going to this car race. You know JeffB I´m not at all interested in cars, thing like that but you know my boyfreind, my guy is a real car fan. Guess I have to follow him, guess I have to stand by my guy. I try, yes I realy try learning a bit or two about this. I realy try, you know I think its more fun charing each others interests. I see you wore the loafers on your trip. A good choise when you had much walking to do. Me I´m always in heels, so also this Sunday. I was wearing my navy blue 4 inch stilleto pumps with a bit pointy toe. Strolling a long with my guy was ok, even me tip toeing inside all the pit garage was ok, well my boyfreind giving me his hand for me to hold on to, (somehow I had this feeling perhaps doing this in high heels wasn´t a good idea, but I managed). Strolling a long was, as I said ok, stand watching the racing wasn´t. My boyfreind let lean on to him while standing, that was good. Yes picking yours loafers for your trip JeffB was a good choise but I´m sure you will ending up wearing a pumps to you skirts real soon. Oh you must trying a shorter skirt and a pair of heel, its looks good and its fun too! WELL DONE JeffB AND GOOD LUCK!

[JeffB]

maninkirt: Thanks for the kind words and compliments. I really appreciate it. Yeah, spending the day in New York in a skirt was quite an eyeopening experience, one I thoughly enjoyed, and I learned a lot about how I made it all work, and how I can make future outings work just as well, if not better. And yeah, I will wear a shorter skirt on my next trip there.

[Thighbootguy]

JeffB -

I glad you recognized the outing for what it was, “a wild and maybe insane idea”.

I think the outfit looks great. If a guy in a skirt can be considered a conservative/casual look, you hit the ball out of the park. I would be cautious about a shorter skirt because I don’t think the conservative/casual look will survive. It definitely won’t survive with heeled boots.

Truly an extraordinary adventure and what a tremendous confidence builder.

I pulled a stunt like that a while back when I took a bus from Reston Va. into Washington D.C. to visit the National Gallery, but I wasn’t going for the conservative/casual look.

[JeffB]

JeffB -

I glad you recognized the outing for what it was, “a wild and maybe insane idea”.

You're preaching to the choir, my friend. Normally, I'm extremely deliberate before engaging in any sort of risky activity, almost to a fault, but in this instance, I just threw all caution to the wind and went on my little adventure, I'm talking damn the torpedoes, full speed ahead! When I think of how easily that outing could've gone off the rails, and in the worst possible ways, I'm amazed I still went ahead and did it.

I think the outfit looks great. If a guy in a skirt can be considered a conservative/casual look, you hit the ball out of the park. I would be cautious about a shorter skirt because I don’t think the conservative/casual look will survive. It definitely won’t survive with heeled boots.

Well, I guess that depends on just how short. In my case, I'd say perhaps no more than two to four inches above the knees, certainly no miniskirt action, I ain't THAT crazy! And while heeled boots would be a problem, flat boots might work better.

I pulled a stunt like that a while back when I took a bus from Reston Va. into Washington D.C. to visit the National Gallery, but I wasn’t going for the conservative/casual look.

You? Not conservative or casual? Shocking! HA!

[Thighbootguy]

I tried a skirt and pumps tonight. This was the first time in a long time I was out without a pair of boots on. I stopped at Pet’s Mart wearing a long sleeved white dress shirt, an ankle length gray wool skirt, black hose and black pumps with 2” heels. No outrageous components, just a classy conservative look. Maybe it’s my sensibility but I think this outfit raised more eyebrows than thigh boots and a leather skirt, which I have worn into this store months ago. I noticed a lady all the way across the parking lot just staring at me as I walked from my car to the store. In the store, the clerks, young kids, gave me a full head to toe look. Several of the folks in the store gave me a longer look than I normally get. No one said a word, at least while was there. I think my observation that if I’m wearing thigh boots with heels, it’s so outrageous that anything else is ignored. A simple skirt and pumps, however, does not have the outrageous element to it allows people to have a reaction to a more normal outfit. I now have much more respect and admiration for JeffB’s grand outing.

[maninkirt]

JeffB I think your legs looking great. Just the legs to have for wearing a shorter skirt Just the legs to have for such skirts you talking about, the hem line ending two to four ich above the knees. Go for it JeffB! You´re going to look great and feel great too. As for the miniskirt, well I was this "crazy" as you said. I was out in a bit of a miniskirt last Sunday, (I have been telling you about it), a 14 inch long skirt, from waist to hem line. A bit daring yes, a bit crazy, well perhaps but I felt great about it. Feeling great, I hadn´t have to feel ashamed of the way I looked. My shape, my figure well they all there and my legs looked just great. Got a few looks from both men and women,. It felt just great and my boyfreind seemed too appriciate my being out in this skirt too. Ha, ha! I would say though I would not wore such a skirt to office. Guess the guys woulden´t mind but at the office, no way. At the office I always go for a more conservative look, a more professional look. As you said, two to four inches above the knees would be fine. Hope I don´t get to long with this. When I started to wear skirts and heels I started wearing knee long skirts working my way up, so to speak, wearing shorter skirts. First I was a bit afraid I coulden´t do it but I did! Me starting dressing in a skirt, in high heels, suddenly I have got more ladies freinds than I had before. Me starting living as a woman, living en famme, yes this has got me more female freinds, more ladies freinds than I had before. I don´t say you are like me but pardon me for wundering, since you starting wearing skirts have you any lady freinds you can talk to, talking about your new way of fashion? Fortunetly I had and yes ITS GOOD TO HAVE. I have the girls at the office, female colleagues and other ladies I get to known lately. Its good, I can talking clothes with them. I can´t talking about things liike this with men. Remember when I staring wearing shorter skirts. The girls at offece just went; "Oh you´re looking great, honey, your legs looking better than mine", things like that. It was great to hear, I felt so good. Oh I hope you too have ladies you can talk too. Perhaps at your work. Pardon me, but what kind of work to you have and are there any women? Speaking of my owv experiance women are more open about this, its more easy talking with to women about this. Just my thoughts. You saying; "and while heeled boots would be a problem". Pardon me for asking, why that, what is the problem? GOOD LUCK STARTING WEARING SHORTER SKIRTS, YOU CAN DO IT!

[Bootking]

Good morning Thighbootguy,

It is really amazing what attracts people's attention and what does not. Most of us would think the opposite, i.e. that the boots would be the provocateur and not the long skirt with low heel pumps!

I know that I could walk around with "women's" jeans all day long, day after day and never hear a remark but pair them with heels, or even more absurd, pair them with usual men's pants and you can actually "feel" the stares!

I guess that's what makes the world go 'round!

[maninkirt]

Thighbootguy Gtreat news, you have been out in a skirt and pumps. Well done. Yes a bit conservative but very feminene. I guess you feeling good wearing this outfit. You´re right this conservative outfit you wore saying so much more about you then when you´re out wearing your thigh high boots and a leather skirt. Everybody sees you. Women sees you, perhap they think, here is a person, a bit like me, a bit like us. You know many women are dressed this way as theirs everyday outfit, in a skirt, a blouse/top, hose and a pair of heels. Me too. I guess many women can relate to you and me, what we feel when dressing the way we do. Yes I think this outfit. Your ankle long skirt, your white dress shirt, your hose, your pumps, perhaps a bit conservative but certainly more eyecatching. You did great! GOOD LUCK!

[JeffB]

I tried a skirt and pumps tonight. This was the first time in a long time I was out without a pair of boots on. I stopped at Pet’s Mart wearing a long sleeved white dress shirt, an ankle length gray wool skirt, black hose and black pumps with 2” heels. No outrageous components, just a classy conservative look.

Maybe it’s my sensibility but I think this outfit raised more eyebrows than thigh boots and a leather skirt, which I have worn into this store months ago. I noticed a lady all the way across the parking lot just staring at me as I walked from my car to the store. In the store, the clerks, young kids, gave me a full head to toe look. Several of the folks in the store gave me a longer look than I normally get. No one said a word, at least while was there.

I think my observation that if I’m wearing thigh boots with heels, it’s so outrageous that anything else is ignored. A simple skirt and pumps, however, does not have the outrageous element to it allows people to have a reaction to a more normal outfit.

I now have much more respect and admiration for JeffB’s grand outing.

Well, I must say that was an interesting outing your had. Also interesting were the reactions to your outfit. Call me dumb, but I thought that after all your previous outings in thigh boots (and with short skirts in some instances), I'd thought that bystanders in your orbit would be long used to your unique fashion sense. I can understand how you must've felt like you were in a fishbowl with the whole world staring at you. Perhaps you're right, that the outrageousness of you in high heeled thigh boots has become commonplace in the minds of most while something as simple and conservative as a long skirt and pumps attracted more attention than you counted on. Again, most interesting.

As for me, because of all the walking I did while in New York, wearing heels was not an option for the distance I covered (maninkirt: That's why I said wearing heeled boots was out of the question), so I imagine if I had, I probably attracted more attention than I planned. In the end, I suppose it's all about perception, that in some instances, a skirt on a guy would garner more attention than boots. I was lucky to have gotten away with what I did, now, if I had worn say, a knee length black knit skirt (I have one in my closet by the way), chances are I would've encountered the same level of unwelcome stares from passersby while denim made me pretty much invisible, probably because of the casual quotent of the garment.

Bottom line: I guess we have to be careful about how we approach this skirt wearing business as we all have lessons to learn about how to do this sort of thing just right.

[maninkirt]

JeffB I understand. You doing all this walking while in New York, yes heels wasn´t perhaps the best option for you. Guess me too, I would had rather picked flat loafers or a flat ballerina shoe for all this walking. You know me, when I had my meeting out of town (perhaps you´ve been reading about it), I was in my stilleto heels all day long (as most of the time). Had a bit of walking and standing in them during the day. I can´t explain this JeffB but I kind of feeling a little bit more "powerful" in my heels standing there talking infront of everyone. My heels certainly don´t make me more powerful. Its just that I feel more powerful, perhaps powerful isn´t the right word but yes wearing high heels makes me fell a bit longer. I´m 167 cm long, so my high heels help me a bit, people would noticing me a bit more. At least I feel this way. I understand you, when you saying; "I imagine if I had, I probably attracted more attention than I planned", and I understand you, you woulden´t have the unwelcome stares from passersby. I don´t say you´re the same as me. Just wanted to tell you, most people I´m meeting from my family, freinds to colleagues, passersby perceive me as a woman. Me too I´ve changed a lot. The way I am, the way I do things, the way I think. You said it our self, wearing a skirt, you have to walk, stand and sit, "like a woman". Me I do all this things and I also has started doing things, thinking the way women do. Can´t explain this better but I realized I do things, thinks in a different way now. It didn´t took me long though to realize, living my new life, living it more "en famme", so to speak, I can´t keep doing things the way I did before. For example, I can´t walk in to room if as I owned the room, with a slouching postures, (a lady doesen´t do this kind of things). Instead I trying being quite delicate with the way I enterer a room, the way I walk, stand, sit and talk. A woman, a lady should be a bit reserved, acting a bit cool. There is so many more things, more "no, no-things" for me now. At the same time I wanted to be seen, to get them lissten to me. For me, most my colleagues are men I have to do everything I can to make them see me, lissten to what I have to say. The good thing is yes I´m accepted the way I am and I´m lucky they perceives me as a woman but this has also made me realize yes to be seen, to be heard in this kind of world, I need my heels, I need to wear a nice outfit. It makes me feel a little bit more powerful. This is just my feelings, don´t know how you are feeling or thinking. Anyway you just did great on your outings. GOOD LUCK ONCE AGAIN!