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Looking good,Jeff ;)

I don't understand why you're nervous about the skirt. At least in these parts a guy in a skirt is a lot more acceptable than a guy in pumps. I've seen lot's of men both on the TV and IRL wearing skirts, but never a guy in pumps (other than heelmeet of course). If you wear both a skirt,nylons and pumps then your outfit get stares. In public I usually wear either a skirt or pumps, but not together. That's just for fun. Or maybe fetish club.

Also I don't get nervous wearing or taking picture, but uploading them to the web is a bit unsetteling:nervous:

To tell you the truth, I'm not sure why I was nervous either. Still don't why. But yeah, I would agree that the sight of a guy in a skirt, with or without nylons and heels would invite a boatload of stares, perhaps more, but I can't bring to wear one without the other. Like I said, I don't see myself going out in public in a skirt, so it's a moot point. Thanks for the comments.

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

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JeffB: Congrats on finding some of your purged pairs and being able to get reunited with them - you still look awesome! You just have that classy look about you no matter what you wear. Maybe it's that infectious smile? pumps: I like your "monthly shopping" pic there. Nice and comfy for a day out getting what you need!

SQ.....still busting societal molds with a smile...and a 50-ton sledge!

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Pumps - that skirt actually looks quite masculine, like a kilt, so you pull it off quite easily. I imagine people did look but probably because it's so rare and unique. That skirt coupled with the plain black tee in post #657 works perfectly well. Glad your neighbour liked it. ;)

Heel-D - Freestyling since 2005

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Shockqueen: Thanks for the kind words. I do as best as I can. Yeah, finding those shoes was quite the incredible stroke of luck. I still can't believe that really happened. Remarkable! HeelD: What I know about kilts wouldn't fill a thimble, but yeah, Pumps' skirt does have that noticeably masculine touch. And he certainly made it work well.

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

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Pumps - that skirt actually looks quite masculine, like a kilt, so you pull it off quite easily. I imagine people did look but probably because it's so rare and unique. That skirt coupled with the plain black tee in post #657 works perfectly well. Glad your neighbour liked it. ;)

Thanks. That picture is currently rated 8.3 on Hotornot, so I guess it's a thums up in that look.:o

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Round two of yours truly in a skirt:

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Just for fun, I thought I'd experiment with a knee length denim skirt, and this one I found at Sears fit the bill which I paired with a white turtleneck, off-black hosiery and my navy RSVP "Crysta" pumps. Why knee length, you ask? Vanity of course, I wanted to show off my legs! Heh!

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Unlike the previous pics I took, this time, there was no nervousness whatsoever. I guess I'm getting more comfortable with the concept of wearing a skirt, and yes, I enjoyed the experience. Still, going out in one remains just than a fantasy. Or so I keep telling myself.

Anyhoo, give me some feedback, positive or negative. I'm a big boy so I can take it!

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

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That's a good outfit, Jeff . I must admit I prefer kneelength myself. It's a bit more comfortable. Most women, I've heard, who likes men in skirts say that just below the knee is best.

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Pumps: While I would agree that a longer skirt would offer more in the way of comfort, I just wanted to show off my legs. Like I said, this was all about vanity. Krapsparov: From hetero man to another, you've got good looking legs in a short skirt too! Heh!

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

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^ At the same time though, this thread is also practical in nature. Designed to help guys develop freestyle outfits that they would actually wear on the streets...based on what they have seen other guys wear on the streets.

Feminine Style .  Masculine Soul.  Skin In The Game.

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Just went to do my monthly shopping in this:

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Talked to one of my neighbourghs on the way. He seems fine with it, even though he's an older guy.

I, myself do not wear skirts or any other artical of (womens) clothing but I like that look. It looks masculine and natural and if I were to see you walking through the mall or down the street, I would have to stop and tell you something like that. Looks good!

real men wear heels

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I never thought I'd say this, but JeffB makes it look natural for a man to be wearing a skirt and heels and still look masculine. I don't know how you pulled it off, but the whole thing just works so Kudos JeffB

He was so narrow minded he could see through a keyhole with both eyes.

Brown's Law: If the shoe fits, it's ugly

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I never thought I'd say this, but JeffB makes it look natural for a man to be wearing a skirt and heels and still look masculine. I don't know how you pulled it off, but the whole thing just works so Kudos JeffB

Many thanks for the kind words. I do as best I can, the important thing is to enjoy what you're doing, and I enjoyed wearing that skirt!

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

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Hey all. Ran up to the mall today to visit one of my faveorite shoe stores, Transit. I've been eyeing a pair of sneaker style shoes, with 3.5" stilettos, over the last few days so i thought I'd pick them up tonight while my parents were out (hehehehe) Anyway, here's a close up of the shoes and a shot of them with an outfit. Let me know yer thoughts!

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Nice pictures Newfie. I can't personally say I like the shoes as they are not my style, but thats just me. At least they go with the outfit though, and as long as you like them who cares what others think.

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Gony, you took my lead with the french pedicure! It looks very nice. It is especially necessarily to have nice toenails when you wear such delecate footwear like that. Let us know if you got any good responses from them.

The persons who i've shown them like too much... My mother dont like and criticize me... But now i can polish my nails ever...

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I didn't expect alot of positive responses for those shoes. They're just the type that you love or hate. But I have a funky taste for shoes anyway.

But today I got some more boots from a friend. She was gonna toss them with some other old clothes to a thrift store, then she offeredthem to me, and who am I to turn down free Boots ;) So they came in the mail today. Here's the pics for your veiwing pleasure.

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Oh, I was out in them today and noticed the shirts in wal-mart, thought they went great with the boots, so I picked them up.

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Hi all, Great work from JeffB and Gony.... I wear a suit to work and sometimes change out a pair of suit trousers and shoes for a matching pencil skirt and pumps/slings. I always match the hem line of the skirt to the heel height, high hem (above knee) = high heel, low hem (below knee) = lower heel. This rule works well. I have often changed just my shoes, and have worn mens suits with 5-6 inch pumps, the trousers were never lengthened etc. so the heel and shoe was clearly visible. Because they were pumps with a low vamp at the front it would have made it obvious they were heels. Due to lack of adverse reaction I pushed it a little further into skirts. I believe if I'm wearing a heel I might as well show my ankles since the shoe looks so much better when you can see it all. It also feels great and the pencil skirts suit the higher heels and suit your stride and associated limitations when walking in heels. I have not been brave enough to consider wearing any sandals etc... yet... rgds Heel-Lover

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Thought it was about time that I shared a picture or two on this thread. I recently bought a new pair of Nine West slingbacks that I am TOTALLY in love with. They have about a 4 inch heel and they are likely the most comfortable pair of heels I have ever worn. Here is an outfit that I put together to wear with them:

1) Black velvet Clayborn Jacket

2) Goffery Bean French cuff dress shirt

3) Nautica jeans

4) Nine West slingbacks

I wore the cuffs over the cuff of the jacket and skipped the cufflinks to give it a more casual look. I am hoping to get a chance to wear this out very soon.

http://picasaweb.google.com/HappyFeat11/UntitledAlbum/photo#5054309577042551554

http://picasaweb.google.com/HappyFeat11/UntitledAlbum/photo#5054309577042551554

http://picasaweb.google.com/HappyFeat11/UntitledAlbum/photo#5054309577042551538

Style is built from the ground up!

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^ Hi HappyFeat.

Here's a direct link to the gallery (as I'm getting Xs):

http://picasaweb.google.com/HappyFeat11/UntitledAlbum

HappyFeat, the pictures you've posted aren't working because you haven't used the proper link to the picture (it should end .jpg - you can get the picture URL by Right-click, Properties on the image you wish to use, copying the picture URL). :o

Anyway, those are some very well co-ordinated outfits! You've got the shirt, blazer, pants (a slimmer and longer bootcut might work better but maybe that's just me) and heels just right I think. Thanks for sharing and I look forward to seeing some more of your efforts. ;)

BTW - these two pictures I like best:

http://picasaweb.google.com/HappyFeat11/UntitledAlbum/photo#5054309577042551570

http://picasaweb.google.com/HappyFeat11/UntitledAlbum/photo#5054309577042551554

Heel-D - Freestyling since 2005

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