That's it .... default mode is skirt and heels.

[Skirted-UK]

A problem I have noticed with these long knit skirts is that they cling to hose. Most leather skirts have a built in lining and my other cloth skirt is knee length and made of a smooth material that does not cling. It never occurred to me that I would soon be shopping for a slip.

If you are going to get a slip make sure that it is cling resistant as some slips can be worse than an unlined skirt for clinging to hose and bare legs.

Its always best to buy a fully lined skirt, especialy when it comes to straight skirts as it makes all the difference to the feel and comfort of the skirt.

Long straight skirts are tricky to wear at the best of times, the last thing you want is a skirt that's clinging to your legs all the time. Chose one that's got a rich satin lining and feel the difference!

[tightlevisandhhboots]

I didn't particularly like the look either, but I figured that I'd try it out to see what others thought. Like I said I only go out in my jeans and heeled boots, or I go out in my kilt with sandles or even tennis-shoes, but I have not done skirts and heels outside of my home. In many ways I think I am just a better Jeans and heels guy than a skirts guy, though I will not give up my traditional kilt nor my utilikilt. TLAHHBs

[tightlevisandhhboots]

Well... trying out the camera and another look with the kilt. This time with LLLOOONNNGG Socks and HH sandles. Again, I won't be going outside in this anytime soon, but I think it looks better than the boots with the kilt. What do you all think?

Thanks TLAHHBs

[NikkiHH]

I've just come back from a 10 minute stroll down to the postbox wearing my black knee length leather skirt, tights and black knee length wedge boots and I have to say it was quite fun! I cheated a bit to start by wearing my long greatcoat (as it is starting to get quite cold here) which effectively hid the skirt as it comes down to just over my knees. The boots were on full show though! When I realised that no one was about other than the odd car driving past I undid my coat and wore my skirt with pride! I've been out and about wearing the same boots and tights with denim hotpants and a shorter coat and that didn't provoke many looks when I went shopping. In my opinion wearing a skirt does put across a very different look and it is harder to get a look I am happy with. Oh well, I guess I have to do some more shopping for clothes and boots, and go out more!! Nik

[JeffB]

Sounds like you had a most interesting little experience, nikki! Glad to hear it went well for you, even though it was a short outing, it was still an outing in a skirt which I'm must have been exhilirating for you. I admire people like you who are bold enough to take such a huge step! More power to you!

[Thighbootguy]

NikkiHH –

I couldn’t agree with you more when you said, “In my opinion wearing a skirt does put across a very different look”. I wear thigh boots and jeans a lot but changing the jeans for a skirt really does change the look. Another factor is the length of the skirt. I didn’t appreciate how much that changed things until I tried a long skirt. The shorter the skirt, the more daring the look (and that isn’t limited to guy skirt wearers).

It sounds like you really enjoyed your outing. I think if you can wear “boots and tights with denim hotpants” you can wear just about anything.

Don’t become complacent, then have a great time.

[Dawn HH]

NikkiHH:-) I agree with Thighbootguy. If you have been out in public wearing boots and hotpants, then you should be able to pull off most things. Congrats with trying out different outfits, including skirts of different lengths. Keep us all posted on your future adventures. Cheers--- Dawn HH

[JeffB]

I don't know if this qualifies as being a "default mode", but yesterday, I took a huge step, or maybe I went too far. I honestly don't know. Following the lead of thighbootguy, I went to a thrift shop after work where I bought not just one, but two sharp looking long skirts, one black, the other gray, both for all of ten bucks. Why I did that I don't quite know, I just felt the urge to do it. So I went with the flow and bought them because I thought they looked neat. After getting home with my purchases, I wasted no time taking pictures, as you see can below:

I spent all of ten minutes pairing those skirts with what I thought were my best looking sweaters, off-black pantyhose and five inch heeled black patent pumps. (Aside, like TBG, I wish I had a slip to wear under those skirts, but wouldn't know how to buy one in my size. The things that go through my mind. Amazing!) After that, came the pictures, and that was where I had a great deal of fun, not just taking the pictures, but wearing those skirts, something I didn't at all expect. You see, the longer I wore the skirts, the more I enjoyed the experience, it got to where it felt....natural, felt good to wear a skirt. I couldn't explain why, but that was how I felt. And I don't mind saying it was a damn good feeling.

I guess the main reason I enjoyed the experience as much as I did was because of how I looked. After previously posting pics of myself in that black leather mini a few months back and having everyone here rave about my legs, I discovered quite by accident that I looked even better in long, clingy skirts like the ones I wore in the pictures above. The visual imagery was stunning to the point of being, well, intoxicating, where it was no long a matter of just wearing something with the heels, suddenly, the shoes were actually secondary, to me, it was all about wearing the skirt, how it looked on me, how it felt to be wearing one. Searching my memories, I can't say I felt quite so excited when I wore the mini.

Looking over the pictures, I found it disconcerting to be wearing the skirt while sporting a beard, that maybe I would've looked better if I were clean shaven instead. That too was how I felt at that given moment. My next thought was what it would be like to wear those outfits out in public, if such a thing was even remotely possible. How could it be done? Where would I go? How would people respond to me? So many questions, and no answers at all. However, the only certainty in my mind was that I looked damn good in those skirts and heels, good enough to think I could get away with going out dressed like that. Frankly speaking, those thoughts flat out amaze me. And, yeah, they excite me too!

Qwll, so much for my ramblings. How about letting me know what you think of the pictures, but, more importantly, all the things I said, and the unusual course I seem to have taken.

[dr1819]

VERY excellent pairing, Jeff, your skirts with your sweaters! If I might comment, however, I think both looks with respect to the "whole you" concept would work far better with a pair of below-the-knee skirts and heeled calf-high (or higher) boots. Just my opinion...

[luxxyheels]

Hmm, I don't know, it's not for me.

[flavio]

I don't like skirts for me JeffB but I have a sugestion to you... Knee high boots would look better then pumps. Why don't you try it and send us pictures? I know you have wonderful knee highs on your closet! Otherwise, the combination of the sweters and the skirts looked very nice!

[Thighbootguy]

JeffB –

Don’t blame me for starting this skirt business.

Both of the skirts look great. I’m not sure I like the sweater with the dark skirt but the grey combination looks awesome. One suggestion, try posing with your heels close together. It would look more like a non aggressive stand than an aggressive stance.

At least 10 years ago I quit wearing a beard after wearing one for 20 years. There were two reasons for shaving it off: 1) it had turned gray, 2) the beard didn’t look right with the style of clothing I wanted to wear. Back then I wanted to try wearing a leather skirt with boots and while not trying to appear as a female the beard pushed my appearance too far in the other direction. The whole thing just looked funny (my opinion).

The three knit skirts I bought were about a foot longer then the ones you found. I think that how conservative a skirt looks is directly proportional to its length. By the way, aren’t thrift stores great for allowing you to try new things on the cheap?

I agree with dr1819 that the look might be better with boots. With long skirt it doesn’t make any difference if they are knee high or thigh high.

My advice on going outside is to look in a mirror first. Make sure the image you see is one you are comfortable presenting. I don’t think I present quite as masculine an image as you do, especially with the beard so I was comfortable with the image I saw in the mirror and went out. As I have said before, what I am comfortable with changes.

I like your look with slacks/jeans and heels and really like the look with jeans and boots. My first impression when I saw your long skirt pictures was that the look didn’t work. The beard was too much. I tried to imagine the look without the beard and it was better but I’m still not sure. Oh well so much for my two cents worth.

[dr1819]

I don't like skirts for me JeffB but I have a sugestion to you...

Knee high boots would look better then pumps. Why don't you try it and send us pictures? I know you have wonderful knee highs on your closet!

Otherwise, the combination of the sweters and the skirts looked very nice!

Ditto, Flavio and Thighbootguy. The style of heel that looks the best is strongly correlated to both the body style and the remaining dress (shorts, slacks, skirt, blouse, jacket, coat, etc.)

Some body styles lend themselves particularly well to spaghetti-strap sandals. I'm not one of them!

Other body/dress styles work well with pumps but not boots. Still others work well with boots, but not pumps or strappy sandals.

It all depends.

In fact, usually the last thing a woman decides on wearing is her shoes. the first is her top, to match her face, then her bottoms, to match her top, then her shoes, to match her bottoms.

Pumps are not the "end all, be all" heeled shoe for all fashions. In fact, heels themselves (gasp!) aren't the choice for all fashions, either. (yes, weep as you must, but it is true).

There are indeed other shoes out there!

Fortunately, for most fashions (but not all), heels work just fine.

[jim]

The style of heel that looks the best is strongly correlated to both the body style and the remaining dress (shorts, slacks, skirt, blouse, jacket, coat, etc.)

It all depends.

I agree DR and find it's something I struggle with constantly. Somedays I really get it "right" and the over-all look is well coordinated and sharp, at other times I mess up with my choice in shoes or with the color or cut of the pants or jacket I want to wear and end up looking like a dogs breakfast.

Still,I believe that any slimish guy with an ounce of courage could wear the skirt, boots and top shown in your avatar and look damn good.

Perhaps even me..

jim

[dr1819]

...end up looking like a dogs breakfast.

jim

Definately LOL! But I've never seen a dog's breakfast... Not sure I want to, either!

Yes, all our efforts to "coordinate" (gosh how I hate that and other "artsy" terms...) are rewarded at the end of the day with little more than polite acceptance into society.

About an hour ago, I ordered a pizza downtown while wearing a black checkered sweater, jeans, and 4" heeled boots.

No one batted an eye.

I paid the deliverer, and ate the pizza.

Then again, I was tastefully well-dressed, even in 4" heels, and not dressed as a freak.

'Nuff said.

[JeffB]

Thanks for the kind, and honest comments on the pictures I posted. Getting feedback means a lot to me. Regarding footwear. I'm sure boots would work better with those long skirts than pumps, to tell you the truth, I don't know why I didn't think of that myself. Perhaps I'll do another round of pics with the boots. Thanks for mentioning that. As for the beard, I've been thinking about whether I'd look better in skirt pictures without it. Perhaps I'll shave and find out. And yeah, TBG, crusing through thrift shops is way cool! I'll have to do that again real soon! And to answer your question, Lindsay, I have been thinking about going out in a skirt, i fthe situation is right. I feel that I'm comfortable enough to give that a try.

[iloveboots]

Hi Jeff,

What a great look. Awesome !! Would love to see how both of these skirts go with your black high heel Boots!

david

I don't know if this qualifies as being a "default mode", but yesterday, I took a huge step, or maybe I went too far. I honestly don't know. Following the lead of thighbootguy, I went to a thrift shop after work where I bought not just one, but two sharp looking long skirts, one black, the other gray, both for all of ten bucks. Why I did that I don't quite know, I just felt the urge to do it. So I went with the flow and bought them because I thought they looked neat. After getting home with my purchases, I wasted no time taking pictures, as you see can below:

I spent all of ten minutes pairing those skirts with what I thought were my best looking sweaters, off-black pantyhose and five inch heeled black patent pumps. (Aside, like TBG, I wish I had a slip to wear under those skirts, but wouldn't know how to buy one in my size. The things that go through my mind. Amazing!) After that, came the pictures, and that was where I had a great deal of fun, not just taking the pictures, but wearing those skirts, something I didn't at all expect. You see, the longer I wore the skirts, the more I enjoyed the experience, it got to where it felt....natural, felt good to wear a skirt. I couldn't explain why, but that was how I felt. And I don't mind saying it was a damn good feeling.

I guess the main reason I enjoyed the experience as much as I did was because of how I looked. After previously posting pics of myself in that black leather mini a few months back and having everyone here rave about my legs, I discovered quite by accident that I looked even better in long, clingy skirts like the ones I wore in the pictures above. The visual imagery was stunning to the point of being, well, intoxicating, where it was no long a matter of just wearing something with the heels, suddenly, the shoes were actually secondary, to me, it was all about wearing the skirt, how it looked on me, how it felt to be wearing one. Searching my memories, I can't say I felt quite so excited when I wore the mini.

Looking over the pictures, I found it disconcerting to be wearing the skirt while sporting a beard, that maybe I would've looked better if I were clean shaven instead. That too was how I felt at that given moment. My next thought was what it would be like to wear those outfits out in public, if such a thing was even remotely possible. How could it be done? Where would I go? How would people respond to me? So many questions, and no answers at all. However, the only certainty in my mind was that I looked damn good in those skirts and heels, good enough to think I could get away with going out dressed like that. Frankly speaking, those thoughts flat out amaze me. And, yeah, they excite me too!

Qwll, so much for my ramblings. How about letting me know what you think of the pictures, but, more importantly, all the things I said, and the unusual course I seem to have taken.

[JeffB]

Never let it be said that I don't listen to my fans:

Beard: off, black thigh boots: on. At the risk of tooting my own horn, I think I look even better than I did yesterday. Please let me know what you think of the new pics!

[new_look]

a big step jeffB, i think no step is too far as long as you are comfortable in yourself with what you are doing. i can echo your comment about when you wear a skirt the heels become secondary, as not so long since i purchased a skirt from ebay myself and i have to say i enjoy the experience too daz

[Dawn HH]

JeffB:-) You looked great in the pics you took of the skirts from yesterday. This is from your no.1 fan. You look a lot better in the no beard and the outfits from today with the boots. And you show a completely different attitude, a much softer attitude, with your feet closer to each other. I also think that the grey skirt outfit is dynamite on you. Now...pull yourself together and go out and see just what the public thinks of your attire. And be sure to let us all know what the results are. Who knows...you might run into that group of young bucs you ran into the other day and you could give them a bit more education on how to act in public. Go out and gobsmack them again. Cheers--- Dawn HH

[dr1819]

a big step jeffB, i think no step is too far as long as you are comfortable in yourself with what you are doing.

i can echo your comment about when you wear a skirt the heels become secondary, as not so long since i purchased a skirt from ebay myself and i have to say i enjoy the experience too

daz

Way to go, Daz!

It's nice to see others enjoying the experience long known since the dawn of mankind that skirts are really where it's at for men.

Pants are for factory workers.

[sscotty727]

I could never get into wearing a skirt, even if it came into fashion for men.

[dr1819]

Have you tried it?

If you never get the chance, just create it. Go to Roaman's (www.roamans.com) and buy a simple jeans skirt. Wear it around the house for a few days.

I guarantee you'll see why men wore skirts for most of the last 50,000 years.

[sscotty727]

No thanks, if they are your thing that is cool. But it's also cool if you don't wish to wear them either.

[dr1819]

Have you ever tried a skirt? If not, how about a kilt? It certainly fits your name, you know!

Besides, as a world traveller, I've grown quite accustomed to seeing men in skirts and skirt-like garments. Any more, when I travel abroad, I usually just wear a full-length skirt anyway. It's far more comfortable and convenient on the plane than wearing jeans. I usually don't wear heels, except during my latest excursion. Probably will continue, though, as I now have a pair of leather boots with full block three-inch rubber heels. They look quite masculine, yet still allow me to street-heel in my full-length black skirt without looking like a pair of "heels."

More:

http://www.kiltmen.com/world.htm

[sscotty727]

I am not scotish, but thanks anyway. As I said, I just don't like the idea of wearing a skirt. Just not for me. If you are into it, cool. But not everyone is. I would never try to talk someone not into heels into wearing them either.

[Thighbootguy]

That look deserves a lot of loud horn tooting. I think both pictures look great. The gray turtleneck looks fine with the black skirt and it goes without saying, I like the boots. To my eye, simple is better. You might try a plain black turtleneck with the gray skirt, or even the gray turtleneck with the gray skirt. Remember you getting advice from a fashion illiterate. I shaved off my beard one time because our office secretary said, “you know, I don’t remember what you looked like without a beard.” I had no idea you would shave yours but it really does soften your image. This is not a suggestion but if I were a talking mirror I’d say the look you are presenting (especially the black skirt) is fine enough to venture out with. Where did this come from? I had no idea either of us were heading in this direction. I do have to admit though, its a fun trip.

[JeffB]

That look deserves a lot of loud horn tooting. I think both pictures look great. The gray turtleneck looks fine with the black skirt and it goes without saying, I like the boots. To my eye, simple is better. You might try a plain black turtleneck with the gray skirt, or even the gray turtleneck with the gray skirt. Remember you getting advice from a fashion illiterate.

Well, don't feel bad about your lack of knowledge in this realm, I'm still figuring out for myself what works with a skirt, so I'm learning the ropes just like you are!

I shaved off my beard one time because our office secretary said, “you know, I don’t remember what you looked like without a beard.” I had no idea you would shave yours but it really does soften your image.

I agree wholeheartedly. Having the beard while wearing jeans or pants seemed to exude a sense of, well, rebel boldness and was a look I liked, but with the skirts, the facial hair just looked incredibly strange, if not highly contradictory, so I decided to get rid of it, and yeah, it does soften my image and makes me look better while in a skirt.

Where did this come from? I had no idea either of us were heading in this direction. I do have to admit though, its a fun trip.

To be perfectly honest, it's a mystery to me as well. Just like I felt that sudden need to wear heels in public five years ago, now I'm drawn to wearing skirts. It didn't take long to realize that I like to wear them, that I look good in them, and yeah, I definitely want to go out in one. I'd even go so far as to say I need to go out in a skirt. I can't understand that feeling either. For the last couple of days since I took those pictures, I've been going over plans as to where I could safely go in a skirt, I'm serious about this and have some ideas in mind which I'm currently fleshing out along with the logistics. But yeah, I AM going to do this, and soon I think.

To be sure, I'll keep everyone posted, and hopefully, I'll have pictures from my journey as well.

[flavio]

It's amazing how many posts come to the forum in a fryday night. And there's nothing like working on a saturday, I just HATE. JeffB, your pics in skirts and boots shows us that you have style! The look is much better then pumps, but see, it's my opinion. You show to every woman in the world that yes, men knows how to match colors, sweters and the whole outfit. Congratulations!!! As someone said before, the pics with the feet closer one to each other looks better too, it doesn't look agressive and, specially, doesn't stretch the skirt wich is a bit strange. Some other guy here (sorry, I couldn't find the post) said that with long skirts, knee highs or thigh highs are the same, I don't thik so! Thigh highs use to "mark" the skirts specially when you're seated, that is not good. This comment came from a girl when I sugested her to use thigh highs and her skirt. So the point is: bellow the knees skirts should cover at least a part of the boots shafts including when seated, shafts no longer then the knee high. But JeffB, congratulations again, yes, I turned into your fan!

[Thighbootguy]

I stopped at the Goodwill (thrift store) today at lunch and they had clothing on a 50% off sale. Normally their stuff is cheap but this was too much to pass up. They don’t advertise these sales but word spreads very quickly and the store was packed. I picked up a black ladies blazer that fits very well and a chocolate brown leather skirt with a built in belt that falls just above the knee. I had seen this skirt before and passed it up because I already had too many leather skirts but ... The skirt was brand new with the original $90 price tag and an extra button and the silica jell packs in the pockets. The label says it is a size 12 but it fits me like a 16. I’m wearing it now with a black turtleneck and black knee boots and the outfit looks fine. I wore the blazer with my chap boots and jeans at Sam’s and Bigg’s last night and the outfit worked well. I walked out of the Goodwill $7 poorer. That is bargain hunting.