Your Questions About Stilettos Bar

Nancy asks…

Ever seen a guy rocking high heels?

Just out of curiousity... I have been wearing women's panties and pantyhose for a while now (26 year old straight married guy, btw). And I also have a few pair of Stiletto heels that I'll wear around the house sometimes. I guess you can say I am a part time crossdresser (Wife is totally OK with it too). Anyways, here's my question... I've done a little research online, and I see all these guys who blog and post about how they wear high heels out in public all the time. We're not talking full on drag, just heels. T-shirt, jeans, and 4-5" strappy stiletto's (NOT cowboy boots or cuban heels). When I see these posts, here is what I am picturing them looking like... http://collegecandy.files.wordpress.com/2007/04/men-in-heels-1.jpg http://s3.hubimg.com/u/724622_f260.jpg I actually think these guys pull this look off fairly well. If I saw a guy wearing these out, I'd look twice of course, but I can honestly say I'd think to myself "That actually looks pretty good!" Now I understand of course that these are models at a photoshoot, and your average guy probably doesn't pull it off this well. But it got me wondering, where are all of these guys from these online blogs wearing their heels? I see all kinds of posts about them going to the mall, going downtown to a bar (not a gay club), or just running errands. I live in a southern big city, and I have NEVER seen this. I think if I took my little at home experimentation to the streets, there would be a good ol' southern lynching! So my question is, have any of you seen guys wearing stilettos or strappy heels in public, and if so, where? What city? Were you downtown, suburbs, mall, etc? And another question, what do you guys think of the "fashion" the guys in this picture are sporting? Do you think it looks good or bad? What would you think if you saw a guy wearing this?

Our pick of the answers:

I have never seen that before in my life, but then again I grew up in a fairly conservative area and just moved to the west coast about a year ago. Anyway, I definitely think the first guy totally pulled it off, the second one I'm not too sure about. I suppose it would depend where he was.

Linda asks…

Has anybody ever seen this?

I keep seeing online about all these guys who blog and post about how they wear high heels out in public all the time. We're not talking full on drag, just heels. T-shirt, jeans, and 4-5" strappy stiletto's (NOT cowboy boots or cuban heels). When I see these posts, here is what I am picturing them looking like... http://collegecandy.files.wordpress.com/2007/04/men-in-heels-1.jpg http://s3.hubimg.com/u/724622_f260.jpg I actually think these guys pull this look off fairly well. If I saw a guy wearing these out, I'd look twice of course, but I can honestly say I'd think to myself "That actually looks pretty good!" Now I understand of course that these are models at a photoshoot, and your average guy probably doesn't pull it off this well. But it got me wondering, where are all of these guys from these online blogs wearing their heels? I see all kinds of posts about them going to the mall, going downtown to a bar (not a gay club), or just running errands. I live in a southern big city, and I have NEVER seen this. I think if I went out wearing 5" Stiletto heels, there would be a good ol' southern lynching! So my question is, have any of you seen guys wearing stilettos or strappy heels in public, and if so, where? What city? Were you downtown, suburbs, mall, etc? And another question, what do you guys think of the "fashion" the guys in this picture are sporting? Do you think it looks good or bad? What would you think if you saw a guy wearing this?

Our pick of the answers:

No, I've never seen anything like that until just now. I think it looks good actually, but as you pointed out, the average guy probably can't pull this off until it becomes more well-known. I would probably think he was gay, to be honest. I know that sounds bad, but it's the truth.

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