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Thank you all for the great comments. I really appreciate it. Ahh yes, the ultimate combo of skirts and high heels. It is indeed very liberating and a definite high. The problem with going out in such a combination for me is that I feel like it's too dressy for most of the places I go to. When wearing a skirt, I prefer the classy look. JeffB for instance, likes his denim skirts which is great for him. However, I'm not a big fan of denim skirts. My skirts are more formal and I felt kind of stupid going to the grocery store in dressy skirts and dressy boots while shoppers around me are in jeans and casual. The only place in the city where you see women in gorgeous classy skirts outfits and high heels is downtown, shops in the mall or evening at a restaurant. Probably in a bar/club as well but I avoid those places like the plague when wearing heels/skirts simply because it's just asking for trouble, at least here. There is a fetish club in town I was thinking of going to but never get the chance. Eventually I'll have to check it out. I've worn a skirts to a restaurant, the movies, a quick trip to the mall (I have a problem wearing 4 inch heels while walking on hard floors for long periods of time) and even downtown. Like you, I've worn the skirt with a coat that kind of hid the outfit. The only time you could see me in full view would be when taking off the coat in the restaurant. With regard to various reactions, They span the reactions I've mentioned in my previous post, nothing extreme or personal. The big difference is that I'm more nervous wearing the combination because I'm more self aware of presenting such an uber feminine look. Theres somthing about wearing pants that make it easier in my head to wear even the most feminine heels. Compared to the number of times I've worn heels in public, I've worn a skirts/boot combo far less. I'm not confident enough to wear pumps and a skirt in public since my inner gut tells me that it's going too far. Maybe if I lived in a less conservative city I'd be willing to take a chance. In warmer weather (weather is also a major obstacle to wear skirts outside) I'd wear pumps and jeans/pants which I have a few times.

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Maximilian!:

Just had to return a compliment. Your boots look great. I like the contrast of brown and black, it has a nice balanced look. Your look could pass as a poster or magazine article promoting mens freestyle heeling. Keep those pictures coming!

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The problem with going out in such a combination for me is that I feel like it's too dressy for most of the places I go to. When wearing a skirt, I prefer the classy look. JeffB for instance, likes his denim skirts which is great for him. However, I'm not a big fan of denim skirts. My skirts are more formal and I felt kind of stupid going to the grocery store in dressy skirts and dressy boots while shoppers around me are in jeans and casual.

Good point. And that's why I prefer denim, because it's more casual than dressy and can be worn pretty much everywhere, most notably on weekends which is when I go on most of my outings. Dressy skirts like what you sported in your pics would indeed look out of place on a Saturday. Sundays? That's a horse of a different color, you could probably get away with wearing something dressy, especially in the late morning as that's what women going to and from church often sport. Nothing wrong with sporting a classy look, I like yours a lot, but you have to tailor that look to your surroundings so you don't stand out like a sore thumb.

I've worn a skirts to a restaurant, the movies, a quick trip to the mall (I have a problem wearing 4 inch heels while walking on hard floors for long periods of time) and even downtown. Like you, I've worn the skirt with a coat that kind of hid the outfit. The only time you could see me in full view would be when taking off the coat in the restaurant. With regard to various reactions, They span the reactions I've mentioned in my previous post, nothing extreme or personal.

Sounds enticing. I might want to invest in a dressy skirt or two myself and give restaurants a try sometime. As for walking on hard floors in four inch heels, perhaps putting cushioned insoles in your shoes might help.

The big difference is that I'm more nervous wearing the combination because I'm more self aware of presenting such an uber feminine look. Theres somthing about wearing pants that make it easier in my head to wear even the most feminine heels. Compared to the number of times I've worn heels in public, I've worn a skirts/boot combo far less. I'm not confident enough to wear pumps and a skirt in public since my inner gut tells me that it's going too far. Maybe if I lived in a less conservative city I'd be willing to take a chance. In warmer weather (weather is also a major obstacle to wear skirts outside) I'd wear pumps and jeans/pants which I have a few times.

An understandable concern, and one I share myself. I prefer pairing skirts with boots as that doesn't present all that feminine a profile, but then, femininity is all in the eye of the beholder. At the same time, you do have to be comfortable with your presentation, and if you don't think you can handle being out in a skirt and pumps, then don't take that risk.

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

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  • 2 weeks later...

Wearing otk boots is a lot of fun but it is a high profile look that I wear on days that I'm super confident. When I do go out in heels, it's usually a more low key look. Like I said before, I'm not purposely trying to stand out in the crowd. I wear what I wear because I like the style and enjoy dressing well (at least I feel that I do and that's the most important thing, self confidence) either in a masculine look or a more feminine one. The following style is a casual one for me, a more day to day heel look. I've gone almost everywhere in this look. The only thing preventing me from dressing like this would be weather conditions such as heavy snow and slippery ice. So what am I wearing? - Calvin Klein grey turtleneck sweater - Womens blue bootcut Jeans (don't remember the brand but they weren't expensive) - Steve Madden grey "Diminish" knee high boots with 4 inch stacked heel. As you can see, I wear them quite a bit. I do like the used look of them and the stacked heel makes one of the best heel sounds I have. They look like 80's boots which I love.

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Max: Great pictures, my friend! You certainly do display a tremendous sense of style. Keep it up!

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

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Love the pics Max....have you worn that look out in public? The boots really look great with that outfit. You look so natural that I would expect there wouldn't be much reaction to the heels. If there was any reaction at all, it probably would have been positive because of the well dressed look.

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

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Pumpfan:-) Thats a great outfit for doing house chores. I'll bet you have great fun wearing that around the house all day. I especially like those black patent metal heeled pumps. Pumps are one of my favorites also. Cheers--- Dawn HH

High Heeled Boots Forever!

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I haven't posted here in a while. Just thought I'd share my housework clothes I'm wearing today.

Hello pumpfan,

That's a beautiful outfit. You look great in it, and it should give you and all a lot of pleasure wearing it. You're a good shape too. nice legs. very smart heels. ;-)

jealousy will get me nowhere.

Love it

:w00t2:

Muddypaws

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Hi everyone.

Not a great shot of my boots, but for an "in the pub" freestyle picture, it does its job.

I also really love the outfit from the previous post as well

http://www.jonrowlinson.com/Skirts/images/Jabez_Clegg.jpg

Cheers

Jon

Cool picture! Great outfit! Terrific boots! I couldn't tell from the pic, but were you wearing fishnets? Sure looks that way to me, if so, your outfit is ever cooler!

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

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Cool picture! Great outfit! Terrific boots! I couldn't tell from the pic, but were you wearing fishnets? Sure looks that way to me, if so, your outfit is ever cooler!

Yup - never go anywhere without me fishnets.I recon you can get away with a gothy kind of look with them. (Not that you have to be a goth to wear them of course)

Never try to baptise a cat

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Yup - never go anywhere without me fishnets.I recon you can get away with a gothy kind of look with them. (Not that you have to be a goth to wear them of course)

Hmm! Interesting! Perhaps I'll give fishnets a try sometime! Heh!

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

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Rule #1 when you go out heeling to a club... BRING YOUR OWN CAMERA!!

Well, here's a few shots from a week ago. My gf (who said she does not mind being in the pic) decided I try a tighter, more "punk" look.

Here's the end result. I do need to lose the remaining 10lbs, but considering my ex wife, ex gf, and both sisters there, and all 4 gave their thumbs up, I'll take it!

Felt good, had a blast!

Good night...

Pic 1 from the house after (due to the camera women not getting the heels in at the club..)....tipsy.

Other pics from the club (#2 with gf)...including another bartender drive-by..LOL

Those shoes are amazing where you get them?

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It’s time to post some more photos of ensembles that I like. "The Saturday executive"

The following photos are a look that I’ve worn in public, one of my day to day heeling styles:

- Alfani black leather jacket

- Baia black cashmere turtleneck sweater

- Levis blue bootcut jeans

- White Mountain black leather ankle boots with 2.5 inch stiletto heel. The heels are low on purpose since I wanted a comfortable yet classy stiletto boots to wear during winter. Even though the heels are low, they have that stiletto heel sensation while walking in them as well as the fantastic clacking noise.

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Maximilian!-- You are not only selling a good outfit, but from the pictures it appears as if you are selling a lifestyle too! Great creative shots with the cigars....I can almost see an editorial developing here of a man in stilettos with two beautiful women near him, in an elegant and regal atmosphere....

Feminine Style .  Masculine Soul.  Skin In The Game.

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Maximilian!-- You are not only selling a good outfit, but from the pictures it appears as if you are selling a lifestyle too! Great creative shots with the cigars....I can almost see an editorial developing here of a man in stilettos with two beautiful women near him, in an elegant and regal atmosphere....

Hmmm! add an ascot, a velvet smoking jacket and a couple of Martini glasses along with the beautiful women, and it would make a wonderful setting for a commercial......;-)

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

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your looking great as usual Max, keep up the good work, you really do know how look your best in boots, worn ANY way!!;-)

here a pic I took late yesterday afternoon in my back yard patio (almost near sunset as you might see) hope you all like it!:w00t2:

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