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Skirting the Envelope


tallguyinheels

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tallguyinheels: Bravo to you on your trip! It certainly made for great reading as you enjoyed quite an adventure, something I've yet to do but definitely would want to give it a try, should the opportunity present itself. You handled yourself exceptionally well from start to finish, exhibiting a calm, cool and relaxed attitude, and that's the only way to go as a male garbed in a skirt and heels. Meanwhile, a purse would definitely come in handy, so would a fanny pack as an alternative option. Once again, bravo to you on your adventure.

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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tallguyinheels

Jolly good effort, that flight must have taken some courage! I flew from Gatwick to Madeira and back last winter in my boots [only 2.5 inch heels] but cheated by wearing my long kaftan [pictured earlier] and did not even have to remove my boots! I endorse what you say about the comfort of a skirt particularly when sitting for long periods in an aircraft or car. They are kinder to what one friend of mine calls his "family jewels"!

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  • 2 weeks later...

Thanks, guys. Another business trip another flight. NYC and Jersey this past weekend. I took the slightly taller and tighter 5.5" heeled thigh boots this time. Didn't wear on the flight up - just because of the foot swelling thing on flights and I didn't want the awkwardness of removing the thigh boots while airborne. Friday and Sunday nights I was left on my own (no company dinners) so on Friday night I wore my long BKE jeans and a black polo shirt - wide belt and the boots. Wandered up to Times Square - no one seemed to take notice - feet got tired by the time I made it back to the Bus Station. Sunday Night was a Skirt Night, this time with a long sleeve red, black & gold dress shirt. I wandered from my Jersey hotel to a nearby restaurant - to watch the Yankees game from the bar Funny story, I walked in almost unnoticed, and certainly uncommented, sat down next to a couple on one side and a tall guy (that made two of us) on the right. Ordered a tall draft watched the game, general conversation both left and right about weather, where are you from?, etc. Eventually, I need to use the toilet, got up, and on returning, the guy on the right notices and says, "by God, man, you're wearing a skirt!" loud enough for many to hear. Momentary, I paused and took a half step back, spread my two meter wing span with a smile and asked, "You like the look?" "Not Bad" with a bit of a smile, was his reply, reminding me of Bill Pulman, as president at the end of "Independence Day". Needless to say bit of conversation followed, none abusive, with a few compliments. One from the lady to my left, as they were leaving, "You pull that off, nicely." Though I'm pretty sure from body language she disapproved. Soon the Yankees were challenging and discussions never came back to my heels and skirt. I think it is incredibly important that you really like your look - when you are in our somewhat esoteric wardrobe choices. Confidence follows.

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Thx, all. I do feel comfortable in the outfit. I like the look, a bit professional and a bit of a double take from folks. I still have to work on the "it's my look" comfort zone. I got a big smile this morning from the clerk at the convenience store this morning, and a ??? look from the teller as I did an errand at the bank. Same skirt, red short sleeve top today. The most difficult thing to do is get moving out of the car and taking the first glance. From then on its easy. The taller boots are easier, still looking for that men's size 13 block heel boot, though

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The most difficult thing to do is get moving out of the car and taking the first glance. From then on its easy.

Take it from me, that first step is ALWAYS the hardest, I've been wearing skirts and heels for quite some time now, and every now and then, even I need a few extra moments to leave the car when on an outing. But once I'm away from that safe cocoon, I immediately start to feel better and then I go about enjoying my expedition. Good luck to you on your continued outings!

I don't want to LOOK like a woman, I just want to DRESS like a woman!

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That is such a great look. I love the long skirt and high heeled boots. You look so stylish and comfortable in your outfits. I congratulate you on the looks and I admire you for taking the steps to appear in public dressed as you are and the positive reactions you have received.

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Inspired by JeffB, I decided to try the denim skirt look. A trip to the local thrift store at lunch yesterday yielded the two denim skirt. The first is the one I'm likely wear a bit. Though it is a light blue and light weight denim more suited for summer wear, it was the right size and fits nicely. No vent in the back, the material has a bit of stretch so it comfortable to walk in. The other skirt is more of a lark. A bit tighter, though even more stretchy, the side vents expose a bit more of the thigh boot shafts. Simple black Lands End golf shirt and belt. I need to explore a bit about belts. My belt collection is primarily dull and I think some more interesting colors might compliment my "skirted" look. Ideas and examples are welcome.

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For the thigh boots, try a really short skirt or skort. You may not wear it outside but it’s fun to have one in the collection, and they are generally available at thrift shops. I just acquired a skirt similar in fit to your second one, except it has the length of your first one a single slit in the center of the front that comes up at least 2/3s of the length of the skirt. It really looks great with thigh boots. I will be reading with interest advice on belts. The right one can make an outfit but I have no eye for them.

I dream of a world where chickens can cross roads without having their motives questioned.

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Tallguyinheels

I like the skirt with side vents, I prefer the darker shade. It shows off the boots rather well and, I imagine, will be more comfortable for walking and driving. I would suggest a wide "cowboy" belt to go with the denim. Black tooled leather would be my choice to match the boots.

I am typing this wearing a slim knee length black leather skirt. Sadly the weather is a bit cool to venture out in it!

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thx guys. I was out at lunch in the rain in the light blue for a errand or two (convenience store refill, and Target for a few Toiletries). No comments a few looks.

TBG: the long front slit skirt has a definite appeal to me - now that you mention it... I could see it paired with a top and a long duster overcoat! Is the skirt something like the picture?

MagicHeels: Both skirts are stretchy and comfortable - The one you like tends to ride up just a bit when walking, but you are right it does show off the boots!

http://www.bonanzle.com/booths/ajsdesignerfashions/items/NEW_EARL_JEANS_BLUE_DENIM_FRONT_SLIT_LONG_SKIRT_SZ_P_S

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Personally, I like the tighter one. In my mind, tighter is always better than loose. Also, I agree that with the boots you would do well in a shorter skirt. Hope you enjoyed thrift store shopping...I always love to dig through and see what gems I can find.

Style is built from the ground up!

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Wow,all three like the tighter one... What doesn't show in the picture is in the tight one, you certainly get a complete profile of my rear, like in a tight pair of jeans... The feel is great though, just not the comfortable "hang" of a skirt. Spoken like I've been wearing skirts for years, not just a couple months....LOL

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Wow,all three like the tighter one... What doesn't show in the picture is in the tight one, you certainly get a complete profile of my rear, like in a tight pair of jeans... The feel is great though, just not the comfortable "hang" of a skirt.

Spoken like I've been wearing skirts for years, not just a couple months....LOL

Nothing wrong with giving a nice profile either, at least in my opinion. If you have nice features, don't hide them...don't go over the top, but work with what you got!

After all, if you can get past being self conscience wearing boots and a skirt in public, wearing something a little form fitting should be easy. However, the most important thing is doing what is most comfortable for you!

Style is built from the ground up!

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So yesterday I was in the first outfit, black skirt and coral short sleeve shirt as it was a nice day in ATL. I really like this outfit. so for errands at lunch - I visited TJMaxx (no interesting skirts or Belts), Belk (where I purchased this skirt, I might get the stone colored version today with a coupon it will be just $16), Barnes and Noble (looked at Hi-fi magazines), Target (some black undershirts for winter). Disapointing but typical, not one comment +/- on my outfit. The one behavior that I have noticed since starting to wear skirts is I am tending to watch what I eat (which is still a bit), and I have dropped a few pounds. I also got upset at myself last week for getting the big Wendy's Baconator Combo! Could the skirts be responsible for this attitude adjustment? Not that I'm complaining, I would love to continue to drop weight down to the low 200's (20 more pounds or so). If I work on 5lbs a month, holding my weight over the holidays, by this coming spring I'll have it made! I wonder if that gets me from a size 16 to a 12, LOL.

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A while since my last post... I'm going out in skirts more and more - on the way to work, my typical lunch outings - sometimes on the way home. Yesterday, I took another stretch, I was due for a hair cut, and have been looking for a new salon, and on the way back from skirting in the mall, google mapped my way to a local place, called them and could get in in a couple hours, $30 cut. This place is a bit closer to work than where I had been going. So I leave work a bit early for the 4 o'clock appt. Black skirt, red short sleeve golf shirt, 5.5 thigh boots. It looks a busy from the car's parked outside, but no matter, across the parking lot and in I go! As my eye's adjust from bright sun to inside, a really cute 20'ish girl behind the reception lets out an "OMG!". I guess the appearance of a 6'5" + heels and a skirt @ 50+ years old was a bit too much, but it sure broke the ice, as I said, "That's one of the reactions I sometimes get!" The rest was all business, the haircut was good, though a bit short. In the middle of the cut, the proprietor approached and asked if a customer could ask me where I purchased my boots. That was cool, I said. So the 40ish lady came up and complimented my look, adding "Not everyone could pull that off, you do." Not one thing bad about the whole experience, other than I'll have to wait 4-5 weeks for the next haircut. I wonder what I'll wear next time. As TBG has found, if you frequent places and are recognized it's not a bad thing, it even makes you more at ease... Here is one place where I'll be welcomed and comfortable.

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  • 2 weeks later...

Here are pics:

I've a dress jeans skirt that's about the same length, but it's so comfortable I wear it around my apartment all the time without thinking about it.

Today, they came to inspect (furnace, HW heater, and filter), and without thinking, :chuckle:, I let them in wearing the skirt and my regular (men's) sandals.

They didn't give it a third look (just a second one), and in seconds I was talking with the maintenance manager like we usually do when I run into him on the grounds - friendly, affable (we have a lot of interests in common, but not in the clothing/shoes dept).

Those who really care about us don't make a fuss about what we wear. Those who make a fuss about what we wear really don't care about us.

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Tallguyinheels:-) I like the skirt and boots look on you. You carry it off well. The stiletto heel and pointed toe box show the boots off very well too. I tend to go for the wide black leather belts, or wide black patent belts myself. You can get them in the ladies section of the stores. Try them and see if they do anything for you. I think that they tend to make a better waist look between a blouse and skirt, and changes the look of a dress completely. Belts are big right now. Cheers--- Dawn HH

High Heeled Boots Forever!

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I've found a belt or two to wear - black and wide with a square buckle at a bargain from Target men's selection - and a slightly narrower black belt with a nice round buckle. One other addition to my wardrobe - a waist cincher. Flexees... for two reasons: though I have been loosing some weight I thought I'd like to find my waist again - especially to see how I look in the skirts, and that I've downsized to a size 14 and weather is cooling a bit, Pics to follow soon

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