I’m lucky in that about 1/4 of women’s shoes in my size actually fit my feet. But I also have had a number of heels where I helped myself out by buying them a tiny bit too large and then wearing 2-4 pairs of socks.

I’m not a cross dresser so I have no advice but I just wanted to say, apparently this has been such a historical problem someone made a movie and musical about the situation, the musical is quite good. Not sure I’ve ever seen the movie though.

https://en.wikipedia.org/wiki/Kinky_Boots_(musical)

All that to say: I’m sure you’re not alone

I’m a trans woman - I got mine on longtallsally who make wide, extra wide, extra extra wide and extra extra extra wide sizes.

You could look for wide shoes, not all brand make them. So, instead of looking for size 12, look for 12 Wide (I think it’s usually shown as the letter B, so 12B). I’m a cis woman with wide feet, and this is what I do.

That one time I bought a pair for a joke at a party a few years ago, I just searched on Amazon for high heels in my regular male size. Apparently, some chinese companies custom-make large-sized lady boots on demand this way. I think I ordered them from “Only Maker”, their models seemed to be safe to walk in with wide heels… I checked before whether you need to order a different size - turns out there is no significant difference. Simply order whatever standard size you usually buy. Just make sure that you pick a model with a wider front. Male feet tend to be wider there, which cause the majority of problems when walking. This is especially true if you have issues with normal shoes being a bit narrow in general (like rubbing at your outer toes when walking for a while).

Also remember that high heels tend to be in the category of “sitting shoes”, not “walking shoes”. I learned that at said party fairly quickly.

While my cross dressing days are over, my town has a kinky shop where you can find drag shoes in large size. It may be an option for you depending how big is your city.

However, I did only use gender neutral sneakers, I am way too tall for heels, and even flat girly shoes in large size are out of my budget (Expect we’ll above €100)

Akira store sells them.

My best advice would be to go in somewhere supportive and safe and get fitted properly, you can cause a lot of damage to your feet and ankles.

Also, start off with a low height and work your way up ☺️

If youre comfortable enough to risk getting outed IRL, theres are certain vendors that cater specifically to crossdressers. The ones I saw were crazy expensive and weren’t particularly pretty. They’d tried to make them pretty but I think theres only so much they can do when focusing on size and strength

I don’t really cross dress, but I have a pair of heels kicking around for a Halloween costume (Monty Python Lumberjack) and I occasionally trot that costume back out.

I basically went to payless (back when that existed, I guess the modern equivalent in probably mystery Amazon brand shoes) and found a pair that more-or-less fit. Staff was actually pretty helpful, apparently around October a lot of guys wandered into payless looking for heels for a Halloween costume. They pointed me right to where the biggest heels could be found.

I think getting a cheap pair was the right move, because they pretty quickly stretched out to better accommodate my feet. I have fairly wide feet even by male standards, and actually found them to be reasonably comfortable all things considered after they broke in (which didn’t take long, those shoes definitely weren’t designed for the stresses of a 200-whatever pound man moshing in them at a Halloween concert)

The harder part was trying to find a bra that even remotely fit my frame.