Skirting the Envelope

[tallguyinheels]

OK, many of you have stretched the envelope for heeled wear for men... I am a more conservative wearer, but enjoy my heels with pants and Jeans - traditional men's wear, except for the shoes...

I have been thinking about adding some outfits to compliment my first boots. Some Capri pants perhaps.

While browsing the store sites for possible bottoms I came across this at Belk:

http://www.belk.com/AST/Main/Belk_Primary/Women/Shop/Skirts/Below_the_Knee/PRD~18025561961364/Kim+Rogers+Long+Twill+Skirt.jsp?off=20

A long skirt, conservative, about the same length as a Capri pant, but more so something I believe I could wear in public. Pleaser Seduce 5.5 inch thigh boots, Ostrich Skin Belt, Men's Ralph Lauren short sleeve in Coral. What do you think?

Shirt: http://www.ralphlauren.com/product/index.jsp?productId=3544459&cp=1995989.2154580&ab=viewall&view=all&parentPage=family

[tallguyinheels]

Here are pics:

[tallguyinheels]

OK, many of you have stretched the envelope for heeled wear for men... I am a more conservative wearer, but enjoy my heels with pants and Jeans - traditional men's wear, except for the shoes...

I have been thinking about adding some outfits to compliment my first boots. Some Capri pants perhaps.

While browsing the store sites for possible bottoms I came across this at Belk:

http://www.belk.com/AST/Main/Belk_Pr...irt.jsp?off=20 $20!

A long skirt, conservative, about the same length as a Capri pant, but more so something I believe I could wear in public. Pleaser Seduce 5.5 inch thigh boots, Ostrich Skin Belt, Men's Ralph Lauren short sleeve in Coral. What do you think?

Shirt: http://www.ralphlauren.com/product/i...entPage=family

[Cuban Nicky]

The skirt and boots are a terrific combination. Go for it

[Elegant]

Nice combination, but I think that you'd look better in a long-sleeve shirt or after shaving your arms.

[tallguyinheels]

Appreciate the comments... I really have no desire to shave my arms or legs... did that once - I was a competitive swimmer. When it get's a bit cooler I'll don some long sleeves. I really like the color of the shirt to make it pop off of the black. About the skirt, a bonus feature is that is has somewhat usable front pockets, enough for keys on one side and a money clip or card holder on the other. Else I'll get myself a black shoulder bag. I could not decide whether to get the stone colored skirt or the black. Both looked pretty good, I picked black owing to the fact is we are approaching fall - though the sales lady said the lighter color will work into fall.

[tallguyinheels]

Sorry to keep the posts... But I'd like to fortify the words of encouragement often expressed here. At lunch today, I switched into the skirt and boots pictured and went to at least think about a public appearance. Now, I've never been out with so much shoe exposed - essentially from the shin and down. No hiding these heels! And I'm in a skirt for the first time. TBG might chuckle a bit. But this is a big nervous step for me. Yeah I know, for others' experiences posted here that no one would make a big deal.... But, I remember JeffB's trepidation on his first skirted outing. ...as well as my own first heels public experience. I think it took almost three weeks of heel wearing in the car and private walks in isolated spots before I ventured where others would see me in high stiletto heels should they choose to look. So I pull into the QT convenience mart. Lot's of traffic, I chicken out. Gotta mail a Jury Duty response with the post office in the next strip mall. I get out of the car, planning on walking 100 feet to the side of the parking lot mail box. There's lot's of people to & from adjacent retaurants, but I get out of the car at least - walking to behind the car... a couple guys pull in to the slot next to me - passenger side - I hop back in my car. Mad at myself, I drive across the street to another strip mall - mainly retail, TJMaxx, Marshalls, Staples, etc. This time I get out, walk 50 feet or so to the covered walkway connecting the stores. For the first time I'm in a place where someone could see me. And a 60'ish lady actually walking toward me on the walkway actually does. I pull out my phone and turn away as she passes. She doesn't turn around after that - I return to my car. Frustrated with myself... I drive around the corner where there are a couple of empty stores - and no one within a couple hundred feet. I get out and walk toward my reflection in the darkened stores windows. Then stride a bit along the walkway admiring my appearance. Dang - pretty good! Heels, skirt up to my waist - giving me the nice long legged look - complete different than my, in flats, disproportional very long torso, short stubby legs appearance. This is why I like to wear heels! With TBG in mind, I drive up the parking lot a way to the Barnes and Nobel - Heck, I needed to relieve myself from the diet sodas I had consumed in my frustration, and I told myself I was not going to change until I had done so. I get out, a couple of ladies talking near the entrance, but I just walk past then and through the door. Yes, they both turned and looked, with the one mostly facing me gesturing, but nothing said while I was in earshot. Removing my sunglasses, I thought to myself, before entering the second set of doors into the store, "They are probably going to discuss the fine looking man wearing stiletto boots and a skirt in a bit." Head high in my finest stride I head for the the restroom, I really needed to... A man was in there washing hands, but paid me no notice as I walked behind to a stall. OK, the heart is going a bit, I calm myself down, wash hands and exit back to the store toward all the magazines. It takes me a while to find the audio mags of interest to me. At least five guys are in the area - all take looks. What to I care! I look good! Where are the ladies in this store? OK, I pick out a Brit Hi-Fi mag, on the bottom shelf, so I have to kneel all the way down in the skirt , which I do in my best lady like squat (I know, in this long skirt I could do a butt up, bend at the waist maneuver, but not very classy and I'm actually feeling very classy in this outfit!) I stand, thumbing through the articles, decide it's worth a $10 purchase, and head to checkout. Now, I decided to walk the direct route to checkout that runs right beside the half full Starbucks, so now at least 2/3 the people in the store have had a chance - and likely have checked me out. Still not an audible comment good or bad. Only one clerk and a another customer in line before me. A young man in his 20's, didn't turnaround until after he checked out and then did a big noticeable double take and a look up and down stare as I focused my attention on the checkout clerk's greeting to me. Then, imagining my best JeffB impersonation, I figured, gone this far, I walk past the exit doors into the Starbucks's and celebrate with a cream soda and triple chocolate chip cookie! I sat down and relaxed and read my magazine for about 20 minutes. I felt much more at ease when I got up and left. Cant' wait for my next heels experience.

[Henri]

Congratualtions. It felt good; didn't it? Henri

[HappyFeat]

What a wonderful experience for you! One of the fun things about skirting is that you go through a lot of the same things again that you had to when you started heeling. Its almost like having to learn the same lessons over again, but the outcome is typically the same - its a fantastic liberating experience and the reactions are minimal and are usually simply neutral surprise. What impresses me the most is not only your confidence, but your enthusiasm for trying something new. It seems to me that you wore your skirt because you really wanted to try it and your intuition served you well - it will likely be something you enjoy from time to time. Also, I love that you credited TBG and JeffB, who are true inspirations to many of us, realizing that we don't have to rewrite the "book" on freestyling, we can learn so much from each other. You also give some wonderful advice for novice heelers, such as telling yourself that if you need to relieve yourself, you will have to do it in your heels/skirt, etc. Finding that little extra to push yourself if sometimes all it takes. Don't worry about the apprehensiveness at first, though I have heeled many places, in many different outfits, etc. sometimes, I still find it hard to get out of the car. Your story is great and you should be quite proud. Finally, I love your outfit. The contrast of the coral top with the black skirt is quite tasteful and understated. Typically, I don't go for longer skirts myself, preferring knee length, but with the very tall boots it is quite spectacular. I usually never wear heels much over 4 inches, so my hat is off to you. As for shaving, to a degree I agree with Elegant in principal, but not about shaving arms. If my legs are hairy I either don't wear a skirt or cover my legs with opaque hosiery of some sort. To me, a skirt requires shaved legs, or some facsimile, but I wouldn't worry about the arms. My logic is that we are still guys and some of us have hair on our bodies. I see myself adapting traditional female items into my male wardrobe, not simply following existing rules for fashion observed by most women wearing them. Its just a case of taking an item and making it YOURS, which I think you did brilliantly.

[JeffB]

tallguyinheels: All I can say about your outing is this----BRAVO!!! I thought you did an absolutely great job in your initial outing in a skirt and heels, your outfit was tasteful and you carried yourself quite well. I'm also humbled that you drew on my own first skirt experience for inspiration and then built upon what I had done. You're right, that very first time was indeed more than a tad unnerving, I felt plenty of butterflies, but once you've gone ahead, there was no turning back, it was full steam ahead and see what, if anything would happen. And when you discover that the world didn't come to an end because people saw you, you automatically wonder what all the worry was about. If anything, you did something I've yet to do: visit the bathroom in a skirt! Wow! But then, I hate using public restrooms, so I always relieve myself before leaving home and then I limit how much I eat and drink while out on a jaunt. Like HappyFeat had said, you are to be admired for your confidence, doing as much as you had on that first adventure. I could tell that the longer you were out, the more you were enjoying the experience, just like everyone else who's discovered the joys of something new and exciting. I applaud you for your outing which I thought was a winner. I hope to hear more from you about future outings!

[tallguyinheels]

Happy Feet: Thanks for the encouraging words. It's interesting, that up to a couple weeks ago I would have never thought of wearing a skirt. I'm 6'5" 230lbs, an athlete - or use to be - I couldn't picture my self-image in a skirt. It was almost like the skirt picked me... Or perhaps the tall heeled boots that I bought on a whim, picked the skirt. "Silly to have boots if you aren't going to show the shafts, right?" As for tall heels, If I could find my size (14-15) in a more conservative block heel, I'd go for it. I really, don't mind the 5" heel at all, I've lot's of miles in them, and with me about 10% taller that the average male, a shoe 20% taller isn't so bad... and, of course, equalizes my not quite balanced God given body proportions as mentioned above. JeffB: Thanks, and, well, you are a fashion inspiration... Another plus... I can start shopping for other skirts. And, I think, I'll focus on loosing about 2-3 inches of waist - so a higher waisted skirt might fit a bit better. And then a top to match???

[HappyFeat]

...It's interesting, that up to a couple weeks ago I would have never thought of wearing a skirt...

I think this is just part of the natural evolution of freestyling and heeling. Once you get the mojo to wear your heels whenever and wherever you choose, it is easy to start looking at the next step - skirts, crop pants, etc. I know that this does not happen for everybody, but it sure has for me. I think there is a line where people begin to stop. I know that some guys only wear boots for instance, but I went for pumps, then peep toes, then sandals, then women's jeans and trousers, then gauchos and crop pants, then to skirts, and dresses. I have even experimented with jewelry and other accessories such as scarves. I think I have reached my limit, but only after years of taking it one incremental step at a time. It is wonderful that you tried something and that you really liked it. It can be a wild ride of unexpected fashion choices.

I'm 6'5" 230lbs, an athlete - or use to be - I couldn't picture my self-image in a skirt. It was almost like the skirt picked me...

I am 6'2" 210lbs and also a former athlete and dancer. At 6'2" I am accustomed to being taller than most people, so I can't imagine what an extra 3 inches does on a regular basis. To a degree I can understand what you are saying, but I always felt a bit conspicuous, no matter what I was wearing, so in many ways I might as well wear a skirt because I will likely be noticed when I enter a room anyway. I have found my stature (and a bit more girth than I would like) to actually be an advantage when out in heels, or a skirt, etc.

I also understand exactly what you are saying about the skirt picking you. The first skirt I ever bought was almost calling to me off the rack. Most every time I have ever tried on a skirt, I just fell in love with it because I thought it looked like it was made for me (at least in my mind.) Now that I think of it, I should wear skirts much more often...

Or perhaps the tall heeled boots that I bought on a whim, picked the skirt. "Silly to have boots if you aren't going to show the shafts, right?"

Actually, last fall I bought a pair of Nine West high shaft boots and the clerk who was helping me told me that I needed to wear a skirt with them for that exact reason. Not 10 minutes after I checked out, I went to another store and the clerk there had me trying on skirts, gauchos, and even dresses. I had such a wonderful evening and didn't get out of the store until I had spent a lot of money and about 20 minutes after closing.

Another plus... I can start shopping for other skirts. And, I think, I'll focus on loosing about 2-3 inches of waist - so a higher waisted skirt might fit a bit better. And then a top to match???

Now, I know you are hooked! I too have wanted to lose some weight so I could drop my size from a 16 to a 12, which gives a whole lot of additional options, not to mention being able to have higher waists fit better. As for finding tops to match...welcome to the slippery slope of building your freestyle wardrobe and hang on for the ride...it will be more fun than you can imagine!

If I may make a suggestion, you may want to try going to Lane Bryant. They are a plus size women's chain with some decent styles and really good sales. I have found many stores (not all) to be quite open to male customers and even let you use their dressing rooms. I am a big fan and go into stores wearing heels all the time.

[tallguyinheels]

Happyfeat: Well, tops from the ladies side may be an issue... I have Phelpsian proportions - a 6'8" wingspan with broad shoulders & a longish neck. I have big calves and thighs also... So a nice look in a shorter skirt might include some dark tight or leggings. I guess I might be soliciting much advice from the experts here.

[JeffB]

It's interesting, that up to a couple weeks ago I would have never thought of wearing a skirt.

Just like with you, wearing a skirt took me by surprise too, so you're not alone in that regard. Originally, I did it on a lark, just to see what it would be like, now skirts are pretty much all I wear on my expeditions. Once I came to realize just how much fun and how exciting it was to wear a skirt, especially with heels, I just couldn't get enough. I look at this as something of an ongoing evolution in my freestyling. Several years ago, I was a nervous nellie wearing mannish looking clunky heels under long pants, now I'm itching to wear a dress and stilettos without caring what people think of me in such an ensemble. Of course, not everyone heels desires to go the same route you, me, HappyFeat and Thighbootguy have gone, but that's the beauty of our unique passion, that being all the different avenues we can travel to satisfy ourselves. It sounds like you're just scratching the surface and you sound excited about your freestyling future. Reminds me of me not too long ago. Heh!

I'm 6'5" 230lbs, an athlete - or use to be - I couldn't picture my self-image in a skirt.

Well, I'm 6-2, 210 pounds, but I've never been an athlete, and, in the beginning, I couldn't picture myself in a skirt either, but after that very first wearing, my opinion changed. The combination of a relatively slim physique (I could stand to lose five to ten pounds) and long legs makes me look pretty darn good in a skirt.

It was almost like the skirt picked me... Or perhaps the tall heeled boots that I bought on a whim, picked the skirt. "Silly to have boots if you aren't going to show the shafts, right?" As for tall heels, If I could find my size (14-15) in a more conservative block heel, I'd go for it. I really, don't mind the 5" heel at all, I've lot's of miles in them, and with me about 10% taller that the average male, a shoe 20% taller isn't so bad... and, of course, equalizes my not quite balanced God given body proportions as mentioned above.

Perhaps that truly was the case. Your outfit looked great and fit you to perfection. It was tasteful and stylish, just like what any woman would wear. You should be proud of your sense of style and do all you can to further develop same because it's extremely important to look your very best when wearing such outfits in public. Perception is EVERYTHING! The idea isn't to make people think (or say aloud): "Eww! It's a guy in a skirt and heels!", rather, "Hey! He looks pretty good in that skirt and heels!" Now, this is just me, but I wouldn't fixate on block heels, wear something fun, and for most of us, that's spike heels. They're all I have and I love wearing them. Look at it this way, a three or four inch spike heel can also look conservative if paired properly with the right outfit.

JeffB: Thanks, and, well, you are a fashion inspiration...

Thanks for the kind words. I simply do as best I can. Again, when you're out and about in public, it's crucial to be fashionable.

And, I think, I'll focus on loosing about 2-3 inches of waist - so a higher waisted skirt might fit a bit better. And then a top to match???

My, my! Aren't we enthusiastic? HA! Hey, why not? When you start thinking about fashion and style, that goes a long way towards looking your best when in public. Go for it!

[Thighbootguy]

Tallgyuinheels –

Last February I started a thread Guys path in Heels at which you might take a look. It seems to have summed up the path you have started upon and gives some cautionary notes.

I think you outfit looked great and my only comment might have been about keeping the waist parallel to the ground but it sounds like you’ve seen that already.

Of all the places to go on a first outing…”Head high in my finest stride I head for the the restroom”. That adventure is probably the hardest to do of all. Congratulations!

A couple of random thoughts on heels and skirts:

• If you’re going to wear this stuff, be sure to enjoy yourself.

• Don’t let the folks on this board lead you into something your not ready for. No one here would intentionally do that but we don’t know how your head works when you read of our adventures.

• On this journey, take small steps (with high heels small steps look better but that’s not what I mean). You don’t have to get to the end of the journey on with one step.

• This really is a mind game that you play with yourself and a game that you can win in fact it is hard to lose because you learn about yourself as you play.

• Present yourself with confidence (no matter what you’re wearing). Learning to do this is one of the positive things that you learn wearing skirts and heels that caries over to the rest of you life.

Enjoy and have fun

[tallguyinheels]

Thanks JeffB and TBG... TBG, you are, of coarse, correct when you say, "If you’re going to wear this stuff, be sure to enjoy yourself." And that you need to feel comfortable in what you wear - not only physically comfortable, but comfortable in your self image, and then you can learn to become comfortable in public in your outfits. Baby steps... Yes, I don't think I'll voyage out in a 15" miniskirt anytime soon, if at all. But, I'm looking forward to pairing my new long skirt with a few different looks this fall. Suggestions welcome from HHP folks of course. What I'm also looking forward to, now that I've passed the "stealth" free-styling position, is a few open discussions with people I may meet.

[tallguyinheels]

Tuesday is wear a skirt day! Same Skirt, different shirt, 5" patent kneeboots first then the slightly higher heeled thigh boots. I've been kind of ambivalent toward the patent boots with jeans. They look better with dress slacks like I wore yesterday, but still they stand out. What do you think about them with the skirt? Standing out isn't an issue 'cuz any heel is going to stand out.

[NewfieGuyInHeels]

Okay, so before the summer season I got myself a black Original style Utili-kilt. I love it, I wore it more the summer than I did shorts or pants, tho I never considdered actually wearing a woman's skirt. But I've been looking it up, doing a bit of light reserch and I've been finding tons of sites where ppl are commenting that it makes more sence for a man to wear a skirt than a woman, just based of anatomy alone. And the only real time pants are useful to a guy is when riding a horse or bike (motor or otherwise). So just yesterday I picked up a knee stretch denim skirt for my gf for her b-day in a couple weeks. It turned out to be the wrong one, but me being me, I had to try it on. And I think I like the look of it. I won't discribe it cause I'm including pics. My gf seems totally cool with the idea of me wearing skirts full time. So i may actually look for denim skirts along the line as the one in the pics below. I don;'t think I'll be keeping this one as I like my jeans, skirts, shorts, whatever to have front pockets, which this one doesn't. Hope to hear your thoughts!

http://i77.photobucket.com/albums/j78/darthraze/Me208.jpg

http://i77.photobucket.com/albums/j78/darthraze/Me207.jpg

[HappyFeat]

I really like the look Newfie. You wear it quite naturally.

[NewfieGuyInHeels]

Okay, so before the summer season I got myself a black Original style Utili-kilt. I love it, I wore it more the summer than I did shorts or pants, tho I never considdered actually wearing a woman's skirt. But I've been looking it up, doing a bit of light reserch and I've been finding tons of sites where ppl are commenting that it makes more sence for a man to wear a skirt than a woman, just based of anatomy alone. And the only real time pants are useful to a guy is when riding a horse or bike (motor or otherwise). So just yesterday I picked up a knee stretch denim skirt for my gf for her b-day in a couple weeks. It turned out to be the wrong one, but me being me, I had to try it on. And I think I like the look of it. I won't discribe it cause I'm including pics. My gf seems totally cool with the idea of me wearing skirts full time. So i may actually look for denim skirts along the line as the one in the pics below. I don;'t think I'll be keeping this one as I like my jeans, skirts, shorts, whatever to have front pockets, which this one doesn't. Hope to hear your thoughts!

http://i77.photobucket.com/albums/j7...raze/Me208.jpg

http://i77.photobucket.com/albums/j7...raze/Me207.jpg

[Magic Heels]

Tallguyinheels: I think that length of skirt would be better with high heel shoes, a shorter skirt would show off the boots which look interesting. Newfie: You look good in a skirt! I have been wearing a kilt during the Summer but am now getting into skirts, pics below. The short one is nice and free and easy around the house, I am starting to wear the slightly longer one out and about but if I want my boots to remain incognito I wear the full length kaftan, which seems to impress people.

[tallguyinheels]

Magic heels... Notice you wide belts and very narrow waist in you pics... is that a natural waist or one that is drawn in? I've been out twice in the skirt with various tops. When I try pumps or my oxfords with the skirt, I'm just not too happy with the look. On the other hand, the black skirt with a bright red golf shirt I wore today looked nice and with the boots appeared a little Christmassy - the boots and long skirt is a more winter or at least fall look. I have been looking at some pencil skirts - knee length or so... like in the attached pic from shapefx.com

[Thighbootguy]

Tallguyinheels –

Watch out for skirts that are cut like the one in your picture from shapefx, Very few guys (Magic Heels excepted) can wear a skirt that tapers in that much at the waist. Some manufacturers make skirts without the tapered waist, or even better, with elastic in the waist to taper it in as much as your shape will allow.

Magic Heels –

The styles you have shown us belie your age, keep it up as long as you can! Old is only a state of mind for which Peter Pan had a cure (to which I subscribe). I like your look with the longer skirt rather than the shorter one and the kaftan in an inspiration. For the shorter skirt, consider a pair of boots with a tighter shaft.

[Magic Heels]

Tallguyinheels

Yes, my slim waist and the belts are genuine. I have always been skinny, just 112lbs when I went in to armed forces at age 18. During my working life I was around 125lbs and after 20 years of happy retirement I am now 130lbs !

I like the pencil skirt in the pic but I am not keen on them. It is impossible to hide the bulge and they are difficult to walk and sit down in!! I favour slightly flared skirts which accentuate a slender waist.

Thighbootguy

Many thanks for your kind advice, compliments and best wishes. You and the others on this forum are a great encouragement for me to carry on Magic Heeling !!

[tallguyinheels]

so it's been awhile since my last post - just busy - not too much skirting - it is a bit stressful to just get out of the car.... Except this week, for business in Montreal, I wore the patent boots 5" heels, with my jeans on the way up, connecting in Charlotte. Jeans and heels night 1 in the hotel bar - unfortunately a somewhat remote by the airport location b/c Montreal is a great city - just no time for touring this trip. Friday night - through abandoned to the wall and wear the black long skirt. - the bar is almost empty - relax and disappointment. Last night I was determined to wear the shirt and boots home - packed all the other clothes in the suitcase for a very early morning rise today - 6:30 flight! So I'm writing this from connection airport - Philadelphia, I'm still in the skirt and heels! I guess if you can make it through security and a long customs line and only hear one chuckle perhaps directed my way, waiting for flight 2 and walking a crowded airport is no stress. Bonus event - waiting for my flight in Montreal two US Customs guys in uniform stopped by to chat - Guess I was the talk of customs force that morning - how I seemed "relaxed and quite normal during the wait and processing" and they asked why the "unusual" outfit. My reply was a bit lame ("Just like the way I look") even though they were all smiles and I was already relaxed. Guess I was the novelty of the weekend. As stated by other - if you just act normally - and make your way about your business all this "hang up" about clothing, footware and what others thinks fade into the background.

[HappyFeat]

Talk about an inspiration! It always impresses me when guys write about flying in heels, but to fly, internationally no less in heels AND a skirt is truly something I find most impressive! It seems that you are confident in all ways when it comes to doing what you choose. Thanks for sharing the experience and giving me a bit of a boost as my skirting season is beginning anew!

[jmc]

<mod mode> Merged "General fashion thread" with this one. Please do not start duplicate threads. </mod mode>

[JeffB]

tallguyinheels: Bravo to you, my friend on your great trip! You've certainly gone further in a skirt and heels than I ever have! I'm certainly impressed with what you've done! And yes, confidence is the big key in doing what you did, and doing it successfully. With Fall here, I'm anxious to go on skirt/boot jaunts in the near future.

[roniheels]

Tuesday is wear a skirt day! Same Skirt, different shirt, 5" patent kneeboots first then the slightly higher heeled thigh boots. I've been kind of ambivalent toward the patent boots with jeans. They look better with dress slacks like I wore yesterday, but still they stand out.

What do you think about them with the skirt? Standing out isn't an issue 'cuz any heel is going to stand out.

I love the look, the skirt, and the high heeled boots that go with them. You look so chic in this outfit and it sounds like the outings have been successful. You've got the right attitude it sounds like you are getting more confident every day. Good luck to future outings.

[tallguyinheels]

Happy Feat and JeffB. Thanks for you comments: I don't really desire to be an inspiration, more so, i just want to get to the point that I am comfortable at times in my "alternative" choices of clothing. The Airport was easy, actually. Left my room in the hotel at 4:15 AM, clerk wasn't at the counter when I walked up - the evening earlier I did walk up in my skirt and heels however to a complete non reaction by the young female desk clerk - so I was on my way out to the cab before she would have noticed. The Cab Driver might have noticed - but said nothing - though we had a general discussion, exchanging "Where you going, "the weather there", "where a have you lived", etc. At the airport, I just kept my head up, stood tall (easy in 5" heels!) walked past many to the counter. No comment or questions by the check in person, like she has almost 50 year old men in skirts and heels at her counter all the time. Each Airport "official" from the baggage check point, security ("passport and boarding pass, please.") stations one through three might have looked a little taken back for only second - if they even cared - looking at my face instead of elsewhere as I advanced in the cue. As stated earlier, the only adverse anything was one younger couples' laughter for just a moment. Sure as I zigged backward and forward though first the security line, and then the US customs' line many individuals noticed and went about their business. My initial apprehension gave way to a relaxed demeanor, perhaps why there were few comments. At security, removing my boots, placing them in the tray yielded a "Those your boots?" from a middle aged female uniformed attendant. JeffB - I may have to go with a purse of some sort though I was carrying my large computer shoulderbag/briefcase. This skirt has a normal assortment of pockets for billfold and currency clip that might not come with the next - my mobile in its belt pouch is easy to handle in any clothing. Through X-Ray, I load everything back in their place - but know where near to put on the boots. Carrying them in hand, I ask another attendant who directs me to a chair a couple aisles over. Had empty seats next to me on both flights (I was a little disappointed at that...) The skirt is very comfortable to fly in, these heels are a little stretchy - but the altitude foot swelling was still noticable and at times uncomfortable - though I did not remove the boots. FYI on the way to Montreal, I did remove my boots and the smell was noticed by me and the passengers in a row ahead - so they went back on. I need to buy a good leather pair of boots to solve this problem that always happens with synthetic material only. Philly airport there was a bus to board with fellow flyers to shuttle us to the main terminal. I know there was some looks but no comments within my ear shot. Philly airport was crowded - but I just walked head high to the restroom and then the gate. most people are so wrapped up with where they need to go they don't even glance my way. Those passing me often take a glance up at me - just in case I am a Amazonian female I suppose. I changed to jeans and loafers at the Atlanta airport, near my arrival gate, as way too many times I come across acquaintances at the airport. But I'm happy with my pressing the envelope - and will be more comfortable next time I go out, I'm sure.