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My Session in a Skirt & Heels


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Posted
I was in the military (Navy), so I'm up on all that Spec Op lingo! Ahh! the memories!

:rofl:

Hey Jeff,

just so happens I'm still in , and have worn my 4" block heels and 3.5" Cowboy boots to my command without too much of a ruckus, even aboard ship!!!

Just can't get away with the skirt and the heels! Though I have worn my traditional kilt aboard ship many times too, just not both at once!

:wink: tightlevisandhhboots

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

Posted

Well after DawnHH’s comments and JeffB’s pictures, I tried the skirt thing this morning. I went on my morning grocery shopping venture wearing a long sleeved blue dress shirt, black thigh boots with 4” stiletto heels, and a black, smooth leather, below the knee length, skirt. That length skirt falls below the top of my boots but often the top of the boots catches on the hem of the skirt which I think detracted from the look. I was really having second thoughts about this but I thought what the heck, let’s see what happens. After I got out of the car, I walked across the parking lot and saw my reflection in the glass door. I didn’t think it looked too bad so I kept going. As I got into the store I recognized one of the register clerks so I wouldn’t be talking to someone that had never seen me wearing my boots. In I went. I didn’t go shopping. I went directly for the items I wanted and right to the register. The clerk was out in the main isle and watched me approach. She asked how I was and if I had found everything as normal, but I said “I’m having second thoughts about wearing this (indicating the skirt), what do you think”. She thought for a second then gave me the “everybody to their own thing” answer, which meant she didn’t like it too much. Other than that comment, no one said a thing or even appeared to notice. I went back out to the car and switched back into slacks and my boots and went back in another entrance of the store. I went into the produce department and selected another item and went to a different checkout register and chatted with the checkout clerk there and got no reaction. Going back in without the skirt was kind of a sanity check. I wanted to compare how I felt wearing a skirt and boots in public with just wearing boots. I’m not sure it was a fair comparison. I am very comfortable wearing thigh boots, and the skirt was a whole new sensation. It was sort of like when I started wearing boots, fun, but afraid of the reaction I would get. I’m also still trying to get used to the look and making sure it isn’t something I mind presenting.

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

Posted

On the theory that going over the falls in a barrel the second time is easier than the first time, I wore a skirt again today. I really thought the one I wore yesterday was too long to wear with thigh boots, so I wore a black suede, mid thigh length skirt with my black thigh boots with 5” stiletto heels, a white long sleeved dress skirt and black hose. I tried several pair of boots until I got a look I was happy with. I even tried my white pair but that was a little too much. The skirt is about the length that JeffB modeled for us. First I did my morning grocery shopping. This time I walked around a bit and (your not going to believe this) but nobody noticed. When I was checking out there was a guy two people in front of me that really did notice :wink: . I think he had never seen thigh boots before and I’m sure he wasn’t ready for a guy in a skirt. He as also a little over charged with testosterone, his eyes got real big and I think he made a snide comment to the cashier. When I got to the cashier there were too many people around to engage in a conversation so I left the store. After work, I stopped in the same store again and went shopping. This time I took a shopping cart. The store was more crowded so I thought I would get more of a reaction. A few guys did a little double take but everyone else ignored me. My conclusion is if you a guy that wants to be ignored, wear thigh boots and a skirt. After the grocery store I went to Sam’s. There were a lot of people in the store and I was using a shopping cart. I recognized the girl that was greeting shoppers and asked, “Is this pushing it a little too far”? She gave me an embarrassed, “Well …”. I took it that it was. Anyway, I went on shopping and most people again ignored me. One guy did speak to me, “Hey, how are you” (just to be saying something), but other than that … nothing. When I went to checkout, there were looooong lines. I only had a few items, so the guy at the deli counter motioned me over. The deli counter is past the checkout registers and placed so that everyone in the checkout lines can see the food. Well, there I was in the deli line in front of everyone. Still not a word or a harsh look. When I got back to the car I realized I had forgotten an item so I went back in without a cart. The same girl was still greeting people and gave me a big smile. I got my item and wound up back in the deli line again. This time when I got to the register, it went blank and the clerk had to call for help to get it going again. The line got longer and longer with me standing at the head of it. As I was leaving the girl that was greeting had moved to the bye bye station and I said, “I normally wear these boots with jeans”. “I know”. “Does this (skirt) make that much difference”? “OH YES … but it doesn’t look bad”. Now I have to reflect on the day. The “guy in boots” image is one I’m very comfortable with and enjoy presenting. The guy in a skirt with or without thigh boots is something I can do but I have to decide if it is an image I really want to present. I’ll have to give this some more thought. All in all it was a fun day. (Edited to clean up a few typos)

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

Posted

That was a most interesting outing you had there, TBG. I found what you wrote to be very compelling as it gave important insight to just what it takes for a guy to wear a skirt in public. I must admit I was mildly surprised you didn't cause more of a stir than you did during your outing, but then, I guess that might have had something to do with familiarity, that people you deal with are used to seeing you in high heeled boots, maybe they figured you'd wear a skirt. Just my opinion. As for fashion opinions, I think that an above the knee skirt would work best with thigh high boots, judging from the pics I took, that's a better look. Overall, I'm sure it was an eye opening endeavor for you. :wink:

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

Posted

Thighbootguy, Congrats on your adventures in skirts. It's not me personally, but I commend anyone willing to challenge the "Norm".

Shafted, the boots that is! View my gallery here http://www.hhplace.o...afteds-gallery/ or view my heeling thread here http://www.hhplace.org/topic/3850-new-pair-of-boots-starts-me-serious-street-heeling/ - Pm me if you want fashion advice or just need someone to talk to.

Posted

Most skirts I've seen being worn with thighboots have been of the "mini" varity. Just below the "cheeks" and just above the boot tops. Looked good on the women....but I doubt I would look good dressed that way. :wink:

Being mentally comfortable in your own mind is the key to wearing heels in public.

Posted

Thighbootguy:-) I commend you your bravery in experimenting with the addition of a skirt to your thighboots. I'm sure that it was an eye opener for you as well as the onlookers that you encountered. Give yourself some more time to experiment before you make any snap judgements on the subject. After all, you have been wearing thighboots in public a lot longer than the skirt. You might want to experiment with various lengths of skirt and gage the public reaction or non-reaction that you encounter before making a decision one way or the other. Never-the-less...I commend you your moxie in doing so and I trust that you will derive great pleasure in doing this. Do keep us all posted on your progress. Cheers--- Dawn HH

High Heeled Boots Forever!

Posted

dr1819

I do have a long black leather skirt that comes to just above my ankles. It looks very nice but it completely hides my thigh boots. The goal was to wear my thigh boots with a skirt so I didn't consider the long skirt. I might try it with my granny boots.

JeffB -

I don't think people had me pegged as a cross dresser, rather a guy that wore odd footware. Part of the reason for the outting was to gage reaction. I was surprised at how little I got. Most people that saw me seemd to go out of their way to ignore me. I really took that as their being uncomfortable around me.

Shafted -

Skirts in public may not be for everyone. They are, however, a very physically comfortable garmet.

I have said before, If you are not mentally comfortable with what you are wearing, you shouldn't try to present yourself wearing it in public. I was mentally comfortable wearing a skirt and the outfit did look good. I'm still working on deciding if it is an image I want to present.

Bubba136 -

I have a black leather mini as you describe and it looks great with either black or white hose and either black or white thigh boots. The combination really does look good but it isn't an image I'm ready to present. I don't like to think about what the guy that was ODed on testosterone would have done if I was wearing my mini with thigh boots.

DawnHH -

Thanks for the advice. I try to not make snap decisions. Going out in a skirt wasn't one. I did have a good time with my outtings and I may try it again before I make a decision.

All -

The one reaction I did get from the girl at Sam's, I felt, was a very honest one. She said that the skirt REALLY made a difference. Her addition that didn't look bad was an afterthought and I think it was offered so as to not make me feel bad about her first comment. I may have to ask her what the difference was (from her point of view).

The outfit I choose, short black leather skirt and thigh boots with 5" stilettos, may have been more suggestive than I realized, I am wondering about how a long cloth skirt and my granny boots would have changed things. I know, there is only one way to find out.

Thanks all for the comments and advice. Additional discussion would be appreciated. I am really trying to wrap my head around skirt wearing.

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

Posted

Still in, eh? Well, that's cool! I imagine the Navy's plenty different from when I stepped on my first ship wa-a-a-a-a-a-a-ay back in December of 1976! I mean, for starters, you've got women on combatants for Pete's sake! That was unheard of when I was sailing the seas! And you've worn your heels onboard ship! Most impressive! More power to you!

:wink:

About the only area where women are still not allowed to serve is front-line combat, such as the infantry forces in Iraq.

Amazingly enough, however, these restrictions don't apply to the contracted security personnel who're tasked to escort VIPs around theater. Although the percentage is small, a few of them are women.

Posted

I have a skirt question. What is the conversion from a women's size to a men's waist, for example: a 36" mens size is a women's size ??

can I reinforce this question. quite a few board members have discussed using low rise (hipster) women's jeans - I assume because of the waist/hip problem. I've never braved the aisles not knowing where to start really. I assume this is a similar issue to the waist/hip shape in skirts too.

/I

Posted

Skirted,

Your story is a classic example of the nature of a clandestine outing, and is exactly why I would recommend heeling in plain sight. It's a lot more embarrasing if you're doing it in secret and get caught, than if you're doing it confidently for all the world to see.

Exactly my opinion!

micha

The best fashion is your own fashion!

Posted

I have a skirt question. What is the conversion from a women's size to a men's waist, for example: a 36" mens size is a women's size ??

If you have a 36" waist you will need a skirt in size 18 /20 UK. If you live in the USA you will need size 16/18, but beware skirt sizes vary a lot depending on the manufacturer and the country that the skirt was made in.

If you are buying your skirt in a shop, take a dressmakers tape measure with you and discreatly measure the width of the skirt waistband on the hanger in the shop. Most shop skirt hangers make it easy to measure the doubled width of the waist band which should be half your waist measurement.

If you are buying a straight skirt, get the waist right and it will be ok on the hips, a ladies straight skirt is 10" bigger on the hips than the waist.

"You can check out anytime you like, but you can never leave ! " The Eagles, "Hotel California"

Posted

Exactly my opinion!

micha

Yes , but its more fun doing it clandestine and making sure you don't get caught! :wink:

"You can check out anytime you like, but you can never leave ! " The Eagles, "Hotel California"

Posted

Yes , but its more fun doing it clandestine and making sure you don't get caught! :lol:

Why? I have to admit that I like solo climbing tours in the alps. But not high heel tours in a moor with park rangers behind me :wink: Are you fascinated about the angst to be detected?

nice greetings

micha

The best fashion is your own fashion!

Posted

I have a skirt question. What is the conversion from a women's size to a men's waist, for example: a 36" mens size is a women's size ??

I've seen manufacturers' size charts vary considerably. For example, one manufacturer's 16 might specify a 34" waist, while another might list it as a 32" waist.

For example, for a 34" waist, here are the following sizes for three outlets:

Roamans: 18W/L

JC Penneys Tall: 18/XL

JC Penneys Plus: 16W/1X

LL Bean: Between a 16 and an 18 / between a L and an XL

For women, selecting a skirt size is fairly easy, as they simply measure their waists, then select that exact size or round up, knowing that the skirt will rest comfortably on their hips. For men, the difference between our waists and our hips aren't as great, so we have an increased need for precision.

Here's the method I use:

I measure around the smallest area of my waist, which for me is an inch above my belly button.

I next measure around the place where the belt on my jeans normally rests, about 2-1/2" below my belly button. It's about 1.5" larger than my waist.

Whenever I buy a skirt online, I make sure the size is not less than my natural waistline, but not more than where my pants come to rest.

If at all possible, I buy belted skirts (minimum 5 loops) as that allows me to position them as needed.

Posted

dr1819: I like the skirt in your avitar.

I would suggest trying: http://www.tomscafe.org/forums/

and

Vendors:

http://uk.groups.yahoo.com/group/utilikilt/messages/

http://www.cityskirt.com/CSFramesSeattle.html

My pic:

http://www.tomscafe.org/forums/attachment.php?s=&postid=65793

The feelings, emotions, and reactions each of us who have taken the step to wear a skirt out in public.

Just as wearing high heels the only person that permission is needed from is yourself to wear a skirt.

-- Brandy

Posted

Hi Brandy...Thanks for posting your pic today. :wink: I'm sure I've seen a photo of you before tho.You were wearing a suit jacket, skirt and dress boots if I remember correctly. If it was indeed you I saw, then I must take this opportunity to congratulate you on your superb taste and sense of fine style. I thought you put everything together very well indeed. Bravo ! jim :lol:

Posted

Nice picture, Brandy. You definitely look like someone who's comfortable in their own skin and has no problem wearing a skirt. More power to you, my friend! :wink:

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

Posted

I agree! I think I've seen that picture posted here, somewhere -- perhaps evenon this forum -- before. Still a good picture and makes the point.

Being mentally comfortable in your own mind is the key to wearing heels in public.

  • 3 months later...
Posted

About the only area where women are still not allowed to serve is front-line combat, such as the infantry forces in Iraq.

Amazingly enough, however, these restrictions don't apply to the contracted security personnel who're tasked to escort VIPs around theater. Although the percentage is small, a few of them are women.

Submarines, too. :D

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