Yes, do it! Surprisingly, heels in male mode works incredibly well. Last year, I had the great pleasure of seeing the stage version of "Kinky Boots" The role of Lola was played by a former winner of Ru Pauls Drag Race. Her femme outfits were predictably fabulous, but the real surprise was when she came on stage in a mens suit, she wore 5 inch heels and looked stunning.
I do it myself, as well. The heels, not the stunning part. But it works. I know it looks good because women give me compliments all the time. Men, of course, say nothing. But who cares? And however it may look, I feel ten times better than that, because it makes my feet look smaller, and my legs look longer.
