High heels are part of a crossdressers DNA and are truly a place where we literally share the pain with genetic women. We can honestly say without reservation that we know exactly how they feel when wearing high heels. When most of of think about going out some where our crossdresser high heels are always part of the plan. The matching purse goes without saying and you should already know that without being told. The challenge for all of us is to enjoy the night and survive and be able to walk the next day. That is a formidable challenge that I have experimented with over the years with some success.
Crossdresser high heels could be made more comfortable if you lower the heel height but in my opinion they wouldn’t be crossdresser high heels anymore. I for one resist the old lady look limiting my heels to 4 inches in certain circumstances with 3.5 being me go to height. I confess to breaking down and buying Vegas Shoes which are not what you think. Not acrylic platform slides but 3 inch heels that are a bit wider for stability. I have learned that walking in Las Vegas is required everywhere unless you get a wheelchair and I ain’t there yet.
When I first started buying heels it was a good news bad news proposition with the good news being that in the 1970’s there was a ton of awesome sexy heels for sale everywhere. The bad news was very few came in sizes above 10 and even that was hard to find so forget an 11 wide. So if you found something that you could not live without and it was a slide or sandal you had a chance of eventually, painfully stretching a size 10 to fit you. A size 10 pump could also work with shoe stretchers and other techniques along with a degree of pain you just put up with. That was the sacrifice for wearing crossdresser high heels.
So fast forward to 2026 and the internet world with many choices for buying shoes online and far greater sizing options you can now buy shoes that are too big for you. That’s a switch but a good one when you think about it because you can eliminate the pinching of your toes and the balls of your feet. However, if that new found comfort creates a new problem of your shoes flopping off because they are too big you still have a crossdreser high heels dilemma. I use a shimming process to dial in my shoe fit custom to my feet.
Most of my pumps are size 11 wide which fit nicely even a bit loose when I first put them on. After standing in them for a while as the evening progresses they can accommodate some foot swelling without discomfort. On occasions where I suspect I will be on my feet a lot especially on hard surfaces like tile or concrete I might go with a size 12 and possibly a 3.25 inch heel. To make the size 12 fit better I insert a pad in the toe section of the shoe to make the ball of the foot more comfortable. A key point is that I never glue it in or peel off the shield on the back exposing the tacky glue. That gives me the option to remove them at any time if my feet swell and they become uncomfortable at any time. If they are not sticky you can just stick them in a side pocket of your purse.
When the pad is inside the shoe it will keep your foot from sliding in as far so it should fit a little tighter in the heel also. There are also pads that they make to keep your heel from slipping that you can use to make your heels fit better but rather than use use both pads its probably better to get a smaller size. I have never used the heel pads so can’t be any help there.
Good advice. Heels are what got me into crossdressing. Happily I am a size 11 too.
Thank you Miss Micki
Now that you mention it I wonder if that is where we all started, from the heels up!
I wear a 12 wide but never owned heels. Are they hare to begin wearing?
First you need to determine your size in women’s shoes which raises the question where you get the size 12 from. If that is your regular men’s size you would need a size 14 women’s because they numbers are about two higher than men’s. That is going to narrow your opportunities to find shoes as most retailers don’t go that high. Once you find your correct size then select a lower heel like 2 inches to begin with and work your way up. I recommend finding online video tutorials of which there are many to teach you the basics then its just practice.
Good luck.
It is hard for me to get heels because my basic foot size is 12W and most places the max size is 10.5! Onlymaker (in China) can get you some interesting stuff at larger sizes. My formula is for each inch or so of heel, add one size to the shoe. This will relieve a lot of stress and still give you that CFM look! Alas! I have had both knees scoped, and any really tall spiky heels force my knees to go high gain (= pain). But clunky heels do stabilize my feet. Takes some wins and losses to figure out what works.
Good advice Michelle.
Thanks
You’re welcome