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Let me start by saying that high heels were my gateway into cross dressing. They were the very first thing I donned as a young boy and they opened my eyes to the joy that I felt when exploring wearing women’s clothing. Heels have been ESSENTIAL in my journey. So much money has been spent on some of the most gorgeous shoes I have ever seen. Unfortunately a lot of them were lost to the purges of my younger years.
Unfortunately, I wear a 13 women’s shoe, so early on it was difficult. I remember nervously buying a pair of heels at Payless while in boy mode. I was probably only 17 or 18 and was just at the end of their size scale at the time. Talk about nervous. But you know damn well I slipped those pumps on my feet as soon as I got back in the car! There is nothing better than that feeling when your heel pops in and the shoe fits
Nowadays it is fairly easy to find heels in my size with internet shopping. Even when I choose to “half-dress” or just do my face because of time constraints, you better believe I have heels on my feet.
My difficulty now is that, with age, high heels of a certain “sexy” disposition are just a great source of foot pain. I am beginning to understand the over 50 cis women that abandon the 4” and 5” stiletto pumps for the much more comfy block heels, wedges and sandals.
Last night I had on a beautiful, flowing purple maxi dress and a pair of strappy high heels with painted toes showing that just screamed sexy. Unfortunately they also left my feet screaming. As the night went on, I found myself in a girly white pair of Birkenstock sandals that made my outfit feel “summery” and light. I thought to myself, “oh Lord, am I getting over heels? Are sandals and flats in my future?” 🤪. “My feet don’t hurt and I can walk!”
I don’t think I’m completely over heels, because they are the epitome of feminine. I do believe that this over 50 girl may be seeing the light when it comes to alternative footwear. (Open Amazon and search for sexy women’s sandals size 13).
I am slowly embracing dressing for my age too. It’s been a revelation that I think makes my presentation look better. You can rarely fight on two fronts and be successful. I’m already trying to conceal my manliness, trying to conceal my age at the same time is unrealistic. So I’m going to be happy being a sexy cougar!
Don’t get me wrong…I KNOW I will be buying heels for the rest of my life. I can’t stop. I don’t want to stop. I just know that I also need some more “sensible” shoes to bring along with me, just like the other gals do.
@dannydior301 Danni, at my makeover yesterday Cindy put me in some ridiculous heels that I could hardly stand in. Then for a longer dress I wore some silver strappy sandals that were gorgeous. Still ultra feminine and I could actually walk in them. Heel size probably only 1 1/2". Lovely.
Hugs, Chrissie xx.
Oh, Danni! At 70, I still love to wear heels. I do find that I'm more apt to go for 3" to 4" instead of 5" now but I will don even those from time to time. I love to dance so finding heels that allow me time on the dancefloor without pain is a big plus. And, I give away the last of my 6" platforms to the clothes closet at Keystone this year. I may be aging, but I'm not ready to give up the feel of wearing a flowing dress with a pair of strappy heels. Sprained ankles be damned!!! 🤣
Much love,
April ❤️
@aprilrhaynes no pain, no gain as they say! I’m with you…of all the things we can wear, heels seal the deal. I can’t ever give them up, I just need to find some that feel a little better. I have a few 4” block heels with a small platform that seem to do the trick for a few hours. As for dancing…girl, you don’t wanna see me try! 😝
Heels and nylons are a must for me when I dress. I am 58 and have most likely topped out at 4-4.5" heels. I dont see me dropping down in the next few years, but some day I will have to start the walk back to 3 inch heels.
@paulapantyhose I keep my legs shaved regularly, so I can lose the nylons in the warmer weather. However, there is something amazing about slipping on a pair of nylons over those shaved legs too. I recently got a very identifiable leg tattoo, so I may be wearing more opaque nylons in order to keep my secret identity a secret.
@dannydior301 Girl, that's why I call'em sittin' shoes! Look fab? AbsoLUTELY! Fun to stand or walk in? Oh lord no. lol
Still...I love the look, so I just pay the price.
I'm might get heels but I have size 12 wide feet and don't understand what size to try
Any advice please
@randialex Torrid has a good selection of wide heels. Some are actually pretty cute. I think their max size is Women’s 13. I usually wear women’s 13 (men’s 11) and have found them to be a little big for me.
@randialex I wear an 11½-12 mens. Finding the right women's size is a bit of trial and error. In most brands I'm a 12 women's, but not always.
For width, I'd echo Danni - Torrid only carries extra wide shoes, but they're fairly inexpensive. Find a pair you like and give it a go!
I agree, heels are a must when I dress I usually wear a 3" or 4" heel
I have always liked gals shoes for as long as I can remember. In the mid 1990’s I tried on a pair of kitten heel sandals and was hooked.
I also have too many pairs of heels, if that is possible.
Since I am too tall, I have always kept the heel height to less than 3 inches.
It’s not so much the height as it is just wearing pretty ladies shoes.
Very enjoyable.
Staci.
Old age and a very creaky old back, means I cant wear anything more than 2" heels an most times a block one at that.
In younger days maybe up to 3" and also but rarely 4". Again, the post wear back pain was hardly worth the trouble
"Nana" caty.
Heels! I already feel apart of after reading all the comments! (first day). 4.5-5” pumps were a dream for a long time. Eventually I built up the courage on Halloween to try on in stores. Wish I felt comfortable in public but too high risk I still feel.
