What Is It About High Heels?

What is it about crossdressers and high heels?

Ask a dozen of us and you will probably get a dozen answers—although several of us may be too busy admiring your shoes to answer immediately.

For many of us, heels have an appeal that goes well beyond matching a dress. They represent femininity, glamour and something we once could only admire from a distance. Slipping into a pair can feel like finally accepting an invitation that has been sitting on the mantelpiece for years.

Then there is what they do for an outfit. A pair of pumps can give a skirt suit a polished finish. Strappy heels can make a simple dress feel ready for an evening out. And if you happen to enjoy showing off your legs, as I do, the appeal hardly requires an explanation.

Heels also make you aware of how you move. Your stride changes. You pay attention to where you place your feet. There is something rather satisfying about hearing your own heels clicking along a sidewalk—especially when, once upon a time, you wondered whether you would ever have the nerve to walk down that sidewalk en femme.

For someone who spent years dressing only at home, that sound can announce a small personal victory.

Of course, my relationship with heels comes with an obvious complication: I am six feet tall before I put them on.

Add four-inch heels and I am approaching six-foot-four. Nobody is going to mistake me for the petite woman who slipped quietly into the back of the room. I may want to blend in, but my shoes apparently have other plans.

Still, I like the look. Tall women wear heels, too, and I have never believed that enjoying a pair should require meeting a height restriction.

There can also be an emotional history tucked inside a shoebox. Perhaps pumps remind us of a stylish woman we admired, a department-store display we lingered over or the first pair we finally bought for ourselves. To someone else, they are merely shoes. To the wearer, they may carry years of anticipation.

And yes, for some crossdressers, heels have an erotic appeal. For others, the pleasure is about fashion, feminine expression or the satisfaction of seeing the person in the mirror look the way they had imagined. There is no single explanation that fits every foot.

Nor does every crossdresser love heels. Plenty prefer ballet flats, loafers, sandals or sneakers. A woman does not become less feminine when she changes into comfortable shoes, and neither do we.

I enjoy my heels, but they are not an entrance requirement for womanhood—or for a successful afternoon out.

Sometimes, though, you put on a dress, add your earrings, pick up your handbag and look in the mirror. Then you step into the right pair of pumps.

And everything comes together.

Wearing Boston Proper

Jonny Beauchamp