This is an interesting article from Luxuo about how heels for men are back in trend. It also gives a little bit of history about men wearing heels.

Inch Up Your Footwear
From Chelsea boots to six-inch platforms, heels are back in trend. As fashion moves into the genderless, men are embracing heeled shoes and looking good.
https://www.luxuo.com/style/inch-up-your-footwear.html
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How to match shoes with a skirt has always been an issue for me. I wear a size 13 mens shoe and have only ever been able to find one pair of heels that work. I look forward to the day when men’s footwear catches up.
I also wear a size 13, so I understand the pain of trying to find shoes to match in the right size. I’ve found the shoes my OnlyMaker to be really nice and comfortable. They go up to size 15 and they have a variety of different styles. I also use Amazon, ebay and the German online store zalando.de.
I’m planning on making a post about where to find heels as a man in large sizes to help other men out. If you have any tips, they’d be most welcome!