how often, where and when have you seen men wearing high heels in public?

In a small country town near where I live, this man wears heels, a dress, wig, makeup etc every day. He is known and liked by the locals and goes by a female name, but has masculine mannerisms and has a female partner. I think it's very interesting (but great!) that this tiny town is accepting of him and his lifestyle choices.

My local city is known for the hero "Pink Umbrella Man", whom, I believe, wears heels, amongst other odd things.

in West Hollywood, i saw a guy wearing high heels, a cutoff sweatshirt and a pair of Daisy Dukes...

Do you mean those high-heeled cowboy boots? Doesn't Bush wear them?

I live in Madison, WI and I have several friends who are cross dressers, MTF, transvestites and I ride the bus with 4 other cross dressers everyday.

iv seen guys wearing high hills in the move jackass

it was hilarious

I am from San Francisco, and have seen many a man in heels.... :o)

i have seen one of my brothers friends in a mini skirt and heels, (he looked good) it was for a frolics thing that is a fund raiser though.

Everytime I look at myself in the mirror baby!

Common scene here (in KL, MY)