[graymnnce]

I think there's a standard answer: depends on the man, depends on the heels, depends on the occasion. I'm one of the rare ones, a man who wears heels fairly regularly. But with a certain degree of restraint: not stilettos, not pointy pumps, not strappy sandals, not... well, you get the idea. Think women's "menswear" shoes for example, with sturdy or wedge heels, maybe a robust but low platform, and styles like square-toe boots, oxfords, loafers - that sort of thing. I like the arch support, the fact my weight is carried more toward my toes, and the sense of a more exotic way of moving through the world, not unlike ice skating.

I grant you, it takes practice to walk without swaying, but the result is not unlike a cowboy's swagger - which, I must add, is in part due to his cowboy heels.