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I quite concur with JeffB and Heel D. Put that outfit on, go out in daylight and tend to your business as usual and don't look back. When it is over you will wonder why you didn't do it a lot sooner. Looking good. Good luck! Cheers--- Dawn HH

High Heeled Boots Forever!

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^ nice shoes.

However, photos of just shoes is not the focus of this thread. The focus of this thread is streetstyle outfits of men in heels. We'd love to see pictures of outfits you wear on the streets or plan on wearing on the streets though. And if you want, feel free to PM me with pics, I'd be happy to help.

Lets show how we take our outfits with heels out onto the streets--and still appear as men in the process. The goal of this thread is to inspire other members to overcome their fears of appearing in heels in the streets by preparing their physical appearance in advance--in the style and fashion sense.

Fear is after all really just a signal that we must all at some point in our lives deal with. Its probably like taking a 3 year old to the grocery who does not want to go shopping with you. You wouldn't let a 3 year old's mentality run your life. Since its groceries, you'd just take the child along with you and deal with it. Fear of wearing heels in the street is probably much the same.

Streetstyle and fashion lies at the heart of this thread.

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Here is what I wore today. I am not styled for the picture--notice how my black pants are bunched up over the shaft of my boots. This is exactly how you would have seen me on the streets though, so the character of my photo is perfectly preserved.

Here is another pic taken on Little West 12th Street in the Meat Packing District.

Feminine Style .  Masculine Soul.  Skin In The Game.

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Yo, kneehighs! Regardless of if you were styled for that pic or not, it's still a great, casual look. More power to you, my friend!

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

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Love the outfit Kneehighs. I was out to the mall yesterday in the outfit below, I never saw anyone looking at my feet at all. and as i was walking I caught a look at myself in a mirror in the housewear dept. of Zellars and my heel was fully visable while I was walking.

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Newfie--I think you could pull that outfit off in almost every social context imaginable. The chunky heel, platform sole, and round toe camoflouge their the sex they were originally manufactured for. ;)

Feminine Style .  Masculine Soul.  Skin In The Game.

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It took years (and mostly being lazy), but I finally took some new pics of me in shoes. My gf and I just went away to Niagara Falls for the weekend. We both just needed to get away and do nothing! This is now our 3rd time there together. We like the fact that you get a half decent hotel for cheap. Plus, you're in a toursit trap! lol

I didn't bring any guy shoes with me. Not even like running shoes that look like guy ones. For driving and just walking around, I wore my Coach optic flats. I love these! Her and I loooove Coach! My gf bought them for me because she knew I wouldn't buy them for myself (they were just under $100 CDN). I have wore these out before to shopping and such at home. Only got one comment from a customer in Aldo's who really liked them.

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I bought these peep toe pumps at 5-7-9 in the states at the end of the season. The make is Rouge. They are 4" high with a 1/2" platform. I know these are those same cliche pumps you see, but I like these because the platform is hidden on the sides. AND, they aren't shiny patent leather. PLUS, they are super comfortable!

I wore these out to dinner one night, with what I had on in the pic but a brown top (same style). There were people smoking outside. They just looked at us like "hey" and then went back to their convo. When we walked inside, about 5 staff members were there and no one did anything out of the ordinary. Well, I lie, we were both looking good so I'm sure they were just checking us out.

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These mules are by Frederick's of Hollywood (my fave make - I got a few pairs by them). They have a good 4" heel. These fit like a dream. They are the perfect around the house shoe. I've been waiting for warm weather to wear them out. Normally, I'm sketchy on mules because most of them flip up too much which causes the pant leg to get caught under your foot. This is ok with flat mules or flip flops, but not really sexy with what you want to wear with them. Surprisingly, these don't flip up that high and work well with flare jeans.

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So those are some updated pics. But now you might ask, "Well, CB17, what was the reaction?". None. Nothing at all. I was in all predicaments: standing in the entrance at a resturant waiting for tables, in men's washrooms, seated at visable tables, etc. There was even a couple of men's oldtimers hockey teams there. No one said boo.

Now, I'm not saying it's easy. It's easy in the sense that people do not really care what you wear. For me, it's more me being a tad nervous on trying a new style, such as the peep toe ones I did. But once you tried, it works well after that.

Wow, I went long, but I hope everyone enjoys them!

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CB17 Love it. Not only in terms that you used this thread correctly, for posting entire outfits that you wore, but for you finding the time and energy to share your pics with us! Thanks.

In my view, I think I like the outfit in #2 the best. The brown top you said you wore probably complements your skin tone well, and probably makes for a more monochromatic dark colored image. Good job!

Excitedly looking forward to seeing and hearing more from you.

Feminine Style .  Masculine Soul.  Skin In The Game.

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CB17 - firstly, thanks for sharing your freestyling pictures with us. You're certainly as I pictured you - looking stylish, well co-ordinated and carrying yourself well.

Outfit #1 - I love the flats. They work well with the jeans. Something I, as you all know already, would wear in an instant. I would love to have seen the whole outfit that you wore with those.

Outfit #2 - well co-ordinated. I really like your peep toes. I've considered wearing peep toes but not gone ahead yet. My girlfriend is a big fan of peep toes. You certainly pull them off no problems.

Outfit #3 - I like the mules. Very stylish. I'm sure they worked a charm with what you wore. I have some heeled and wedge sandals that I'm going to wear over the summer and I hope to not encounter the pant leg caught under foot scenario too.

Can I ask you CB17, have you had a pedicure? Your feet look well groomed. Getting a pedicure was one of the things I had planned to do in NY but unfortunately never got round to it. It's something I'd like to do.

I look forward to seeing further outfits and contributions from you in this thread in the future. It's great see more contributions. ;)

Heel-D - Freestyling since 2005

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This is a pic I threw together in photoshop.

We had a rehearsal yesterday and I couldn't get the buggers to have a group photo. I sneaked pics on the sly and put them together.

As you can tell, the singer (far right) is not even happy about that.

Anyways.....

Black vest top

Trashed denim mini

Nearly black tights

Black ankle boots with small heel (always small when lugging stuff about)

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Never try to baptise a cat

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Heel-D, I actually got fake acrylic toenails on my toes. My gf did them for me from a pack from a drug store. They look really good. I normally just wear a neutral color or pearly white on my toes, but I wanted to try this. Those are cool for every once in a while, but i prefer just straight subtle polish. About pedicures, I have been for them and manicures. I'm in the minority in saying I don't really like them. I feel I do a better job myself. Personally, I don't like the way they shape my nails when I go. I can assure you that even without the fake ones on me, my nails still look pretty damn good.

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Hey all. I wasn't sure where to put these pics, but I hate starting a new thread for something that can go somewhere else. So this outfit isn't something I'd wear out, but it's an outfit none the less, so maybe someone here will like it. The denim skirt in the pics I made from an old pair of jean shorts, which is why it looks so ratty, I'm not much of a tailor ;) I'm not sure what really goes with a Denim skirt so i just threw on a black ribbed T, and the shoes speak for themselves.

Oh by the way, I shaved my legs for the first time today! Go me hahaha.

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I'm not really looking for approval on this outfit, I'm kinda just posting it for fun, lol, hope someone enjoys.

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^ Nice red shirt. Works great with the pants. Good outift. Regarding the skirt - if you ever do have to guts to out in it, I'd go with the boots because it looks better proportioned. I think the MJs will work better with a darker longer skirt or jeans.

Heel-D - Freestyling since 2005

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Thanks HeelD, but like I said, a skirt isn't really my taste for out and about. Mind you I will admit it's nice for around the house. I made the skirt in the first place cause I was just curious what it was like, and I didn't really want buy one. lol

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Newfie The red shirt, black pant, and pointy shoe combo look great! I can see you wearing that outfit in an upscale hotel restaurant/bar. Good color coordination there.

Feminine Style .  Masculine Soul.  Skin In The Game.

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NewfieGuyInHeels: Your red and black outfit looked good. You pulled it off quite well, and the Nine West boots with those delightfully thin heels tie everything together perfectly. Casual, yet stylish at the same time. Add a black leather jacket and the sharpness factor would definitely multiply. I have no doubt you can go anywhere in that outfit. More power to you, my friend! As for the skirt pics, you don't have to apologize for feeling that's not your thing. After all, you were just experimenting, and, to be honest, your efforts weren't too bad. Not every Freestyler can, or is willing to go to the next level of wearing a skirt, and there's nothing wrong with that. But at least you were openminded enough to give it a try.

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

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Finally I have made a pic of me. All you other guys have posted your pics here so it is about time I also do so. The lighting isn't the very best but I guess you can see enough.

When going to town this is what I look like most of the times. Kneehigh boots with a 4", tapered, heel. Sometimes 4-5" stiletto heeled boots or oxfords.

But to Torture Garden..... nah, that was a completely different outfit. ;) (I might put up one in the fetish section some time.....)

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Very cool look, A ;)

I just bought a new skirt. I've been looking for the perfect male skirt and this leatherlook skirt is damn close in my opinion.

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If I was going to a fetishparty (and only then), I would wear boots and nylons.

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Pumps: Let me be the first to say your skirted look is pretty darn cool, especially the one pic with the leopard print pumps. Outrageous! More power to you, my friend!

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

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While we're on that particular topic:

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I blame danielinheels for this (said with tongue in cheek). After seeing the pic he posted back on March 19th in the long black skirt he wore, I was so inspired by how sharp he looked, I decided on a crazy whim to give that a try myself, and that decision led to a happy reunion of sorts. Last week, I went to a high end thrift shop where I found not only the long black knit skirt you see in the picture above, but two pairs of the Renetti pumps I had given away well over a year ago, they being the black and black patent pairs. I absolutely couldn't believe my luck, coming across shoes I had sacrificed in my purge. It was literally a one in a million occurence.

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The skirt was $12.00 and the shoes $10.00 each, and they were still in fairly good condition as it appears they hadn't been worn all that much since I gave them away. I guess there wasn't any need for size 14 women's shoes. So I took my new possessions home where, oddly enough, it took almost a week for me to get up the nerve to put on the skirt, even though I was behind closed doors and drawn drapes. Don't ask me to explain why, I can't, I was just plain apprehensive about putting it on. But eventually I did, pairing it up with a black turtleneck, matching belt, off-black pantyhose and the black leather pumps for my photo taking session.

I was nervous before I started taking the pictures, but I soon calmed down, and, as I did, I remembered just how much fun it was to wear a skirt like I had before when I previously posted pictures here, how comfortable I felt in it, and it shows in the pictures I think. Does this mean I'll eventually venture out in public in a skirt, probably not, like others here who've modelled skirts for pictures, I just don't have the nerve, so I'll be perfectly content to wear skirts in private for my personal enjoyment. With that in mind, let me know what you think about the pics, good or bad, don't be afraid to be honest with me. Thanks!

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

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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:

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