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Chicago Area


Pumpfan

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Living in Chicago in and around the downtown, North Michigan Avenue, River East and River North areas, I have not seen any man wearing heels. I’ve been out daytime, post work hours and evening, weekdays and weekends but have not seen a man in heels. Now you do occasionally come across a CD/TV wearing heels, but that has been all. If you go to some of the clubs where CD’s go, naturally you’ll see men in heels but dressed fem. Maybe I have been in the wrong place at the wrong time, but this has been my observation.
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Pumpfan, if you should happen to find somewhere in teh Chicago area, please pass the location along. As a lifelong resident of the area, I have never seen a guy in heels (again, with the exception of a TV or a few at the Gay Pride parage, which is not quite the same as an everyday location). I also have been looking for a bar that would have a fetish night, where wearing heels would likely be no problem, but all the fetish night places I've read about deal mainly with leather and SM/DM stuff. So if you find a place, pass it along!

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Talk to people at Skyscraper Heels at 2202 West Belmont Chicago. 773-477-8495 I know they have get togethers where you can wear heels as male. Buying shoes there is no problem as a lot of CDs and Queens buy from them. The quality is good and price is fair and I have had a good time buying. You might run into some interesting people also. It is safe. Good Luck Ruby

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Talk to people at Skyscraper Heels at 2202 West Belmont Chicago. 773-477-8495 I know they have get togethers where you can wear heels as male. Buying shoes there is no problem as a lot of CDs and Queens buy from them. The quality is good and price is fair and I have had a good time buying. You might run into some interesting people also. It is safe. Good Luck Ruby

I can vouch for the people at Skyscraper Heels. Gary is great.

Be yourself; everyone else is already taken. - Oscar Wilde

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Ruby John, I also will vouch for Skyscraper Heels. Shopping there is great. From a personal standpoint, their typical heels are a bit too high for me, as there are few pairs under 4" and most are more in the 4.5+ range. They also tend to carry mainly dancer type shoes, and a lot of platforms. Personally, I prefer a more business type heel, so they unfortunately don't have a lot of shoes that I would buy, though I've purchased three or four pairs there over the years. It is an excellent place to shop though. Now, about those high heel get togethers, can you expand on that? Have you been to one? What is the protocol, etc.?

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Beatnix (3400 N. Halsted) is also another good store to check out for shopping. Between there and Skyscraper Heels, they should be able to guide you about the town. I found that Evanston was pretty progressive and has a nice-sized downtown area, no one ever bothered me when I wore women's shoes around there.

Be yourself; everyone else is already taken. - Oscar Wilde

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  • 4 weeks later...

I was hoping to get some additional input from Chicago area guys, but as seems to be the norm, I guess there are very few heel wearers, or, as is more typical of the wonderful Midwest, no one is willing to admit they do! I am not big on wearing spike heels out and about, but certainly have worn some high clunky heels without incident. Unfortunately, I find that the more androgenous styles just do not do it for me. So I was hoping that there may be some city places where the wearing fo a pair of stilettos would be accepted. We did get some repsonses here, but with limited info and no follow up. Come one, Chi town guys, tell us where you go to heel!

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While I just came back from Vegas and saw many, many women in stunning heels (and did much drooling...lol), I did not see any men in heels. So I'm not sure why you would say that! In response to an earlier post, I receive a reply from Gary at Skyscraper Heels regarding places to go in heels. He said that, other than the parties that a group of customers and friends of the store throw on occassion, he did not know of any lounges, etc., where a guy would be readily accepted if wearing heels. I had hopes there, but alas, no such luck.

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RonC, I was in Chicago last year for over 7 months. I heeled all over Naperville area. Down Route 59. A great place for heeling would be Barnes and Noble on 59, and also the Mall on 59. I heeled with a stilleto heel all the time and didn't get any remarks and any views. It was a great place to heel and no one said anything. Hope this helps out.

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