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Posted

Ok, I have been beating myself up for the last 3 or 4 years. I am a discreet high heel wearer (to the bank, mail box etc.). I have been wanting to take advantage of Halloween too... If I may say, "let myself go"... Now I have plenty pairs of shoes, from cheap looking to very nice looking but I don't want to go out looking cheap. I want to grab the attention of the women and show them that... Yes, men can strut just a good as they can.

Ok, my problem is.... Do you have to look cheap on Halloween? I want to go as a Wo-man. Basically, half and half. The top part man, the bottom part woman. Can this be done? or is it too obvious that I am a cross dresser? I mentioned it to my friend (and she does not know I wear heels) and she said, go the opposite way, woman up top and man at the bottom. Of course my I said to myself "NO".

This is the bottom half of what I had in mind.... this or that

Oh... What I forgot to mention. I am a very popular DJ in my city and I will be working (DJ'ing) in front of 400 to 500 people of afro-american heritage.

Ok... what do you think? Too much or is it ok? Thank you for you comments.


Posted

Not the look for me, neither one, BUT, if I was looking I would rather see the "this" not the "that". Hope my input helps you decide.

IF GIRLS CAN WEAR PANTS THEN I CAN WEAR HEELS

Posted

What the heck it is Halloween. I like the 1st look best, but the wedge heel boots may be more comfortable for a long period of time. I also have to say I would do it if it was a costume party. No you don't have to look cheap.

Posted

I like the 'this' look better. I think the half & half costume is a great idea - you can tell people you wanted something that would appeal to both sexes (you have good looking legs in this picture; if you have decent arms or chest, to appeal to the woman, you are set!). If you do this, then I think a simple skirt and simple heels is enough of an outfit to be a woman. I think the 2nd outfit is a little busier, which isn't really needed. Let us know.

Posted

I like This better than That, but mainly because you have nice legs and should show them. However, That is a pretty cool and a fun look for Halloween. I like to do the top half man/bottom half woman thing myself. Its does turn some heads, but the reactions I have gotten were mainly positive.

Style is built from the ground up!

Posted

Go for the first look, and as a club employee, myself, I'd say you'd enjoy the time in heels behind the booth!

I'd have to admit. This isn't my first time working in the club in high heels. It's just this time I will be exposed.

Posted

I have gone cross-dressed a couple of years and no one outside my imediate "in the know" group even suspects I like to do it in private. Halloween is anything goes time. Others will not draw connections like you do so do what you want and don't worry about it. Love the boots too!

Posted

As previously said, "Halloween means anything goes". I would do the first pic myself and show off those great looking legs. Cheers--- Dawn HH

High Heeled Boots Forever!

Posted

I'd have to admit. This isn't my first time working in the club in high heels. It's just this time I will be exposed.

Well if you are ready this might be the time to wear high heels at the club in public exposed. Coordinate your costume with your high heels and because it is Halloween, you'll be able to pull it off. Good luck.

Posted

I'm gonna go the whole hog and look like a drag queen - I wouldn't be surprised if I startled my fellow goths I'll meet :winkiss:. I'll wear a veiled hat, some jewellery, exagerrated make-up [lots of mascara, eyeliner, bloody red lipstick & lip gloss] and pantyhose in addition to my "typical" leather & heels.

What is good for a goose, can be good for any gender!

Posted

I'm gonna go the whole hog and look like a drag queen - I wouldn't be surprised if I startled my fellow goths I'll meet :winkiss:. I'll wear a veiled hat, some jewellery, exagerrated make-up [lots of mascara, eyeliner, bloody red lipstick & lip gloss] and pantyhose in addition to my "typical" leather & heels.

Wow!! Go for it! That sounds like fun

Posted

I'm gonna go the whole hog and look like a drag queen - I wouldn't be surprised if I startled my fellow goths I'll meet :nervous:. I'll wear a veiled hat, some jewellery, exagerrated make-up [lots of mascara, eyeliner, bloody red lipstick & lip gloss] and pantyhose in addition to my "typical" leather & heels.

Man! Get some good pictures and post them here for all to see.:winkiss:

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

Posted

Unfortunately, nothing went like I wanted. I did my make-up and got dressed, but my friends were too lazy to go out, so we didn't meet and there was no party... I regret that. Hopefully, we'll meet in a few hours, because there's Synth/Dark/Goth/Electro party tonight. Unfortunately, no pics, because I've lost my tripod a while ago. But I looked like a Victorian slut, haha!

What is good for a goose, can be good for any gender!

Posted

well Everyone I got my taste of wearing my heels in the club and it was so HOTT and EXCITING!!! My costume was Prince and I had him down to the tee!!!! I had the ruffled shirt, black high waisted pants, fancy black jacket, wig and scarf and 6 inch black kneehigh platform boots. It felt so good I didn't have to explain myself or anything. Any other day I wore my heels and had a litle uncertainty but yesterday was completely different. I felt so free and received so many compliments, high fives and pictures. But I was so pissed off about the contest for it. Originally they were giving cash prizes for the best costume, as soon as I stepped in the door they were finished with the contest. And the person that won looked so busted (ugly) they were "Girl-guy". The person had a red wig with pigtails, a dress, and a face full of hair!! So many people were telling me that I should have been there sooner and that I could have won!!!! I think I would have too but I guess there will always be next year. But all in all it was a great time!!!! This was probably the greatest accomplishment I have ever made. And I owe it all to HHPLACE.org and my girlfriend for you all made this happen for me. After this whole thing I am tempted to just wear my shoes out on the regular I mean I might get more stares but whatever. I will have pictures for you guys in the mere future. Take care!!!

What ya see is what ya get no more or less!!

Posted

Hiheellover23:-) Too bad things didn't go for you as you had planned, but it sounded like that you had a good time after all. Better luck next year. Will be looking for those pics. Cheers--- Dawn HH

High Heeled Boots Forever!

  • 1 year later...
Posted

You may have heard that Halloween now ranks only behind Christmas in the money spent. It is the THE time of the year when you can't tell whose skirts and dresses are shorter, the girls or the guys, and both sexes seem to bring their very highest heels from the closet. It has become something of a Carnival but in late October. It's also, without a doubt, when the inside-the-house heeler can go dressed to the nines to an event with no fear whatsoever. HappyinHeels

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