“No, Those Pumps Don’t Match”: When Women Dress Their Men

Do Some Women Actually Dress Their Men As Women?

Every so often, someone will ask, usually in a hushed voice, as though they’re requesting classified government documents, “Do women actually dress their husbands or boyfriends as women?”

The short answer is yes.

The longer answer is yes, but probably not in the way movies, television or internet folklore imagine it.

Popular culture tends to portray the phenomenon in extremes. Either the woman is a cartoonishly domineering “mistress” barking orders while her trembling husband totters around in six-inch heels or she’s a glamorous makeover fairy who transforms an eager man into the feminine ideal with the wave of a mascara wand.

Real life is usually much more ordinary. And much funnier. Because in many cases, it starts not with coercion, but curiosity.

A wife notices her husband lingering a little too long in the hosiery aisle at Macy’s. A girlfriend jokingly says, “You know, you have better legs than I do.” A husband admits he once tried on a skirt in college. Somebody laughs. Somebody experiments. And before long, there’s a middle-aged accountant standing nervously in the bedroom asking whether the beige pumps or the black pumps look “more appropriate for brunch.”

Civilization advances in mysterious ways.

What’s often overlooked is that many women approach the whole thing pragmatically. Men tend to imagine crossdressing as some dramatic transformation worthy of a movie montage. Women frequently see it as… getting dressed. Which means they immediately begin correcting mistakes.

“No, not that shade of lipstick.”

“That skirt is too short for daytime.”

“You can’t wear open-toe shoes with those stockings.”

“Sit down properly.”

In other words, the average crossdressing husband often discovers the same thing generations of teenage girls learned from their mothers: femininity comes with rules. Lots of rules.

One reason some women become enthusiastic participants is that they enjoy the shared activity itself. Shopping together, discussing clothes, experimenting with presentation, laughing at fashion disasters; these things can become oddly bonding experiences. What begins as “Can I try this on?” evolves into Saturday afternoons browsing sales racks and debating whether a navy skirt suit is more versatile than charcoal gray.

And honestly, many women appear to enjoy the role reversal just a little. After centuries of men pretending not to understand women’s fashion, some wives finally get to say, “Now you know what it’s like.”

There’s poetic justice in watching a man discover that:

•     women’s sizing makes no sense,
•     heels are instruments of medieval engineering,
•     shapewear is a branch of applied physics,
•     and carrying a handbag somehow requires an advanced degree in logistics.

The educational value alone is substantial.

Of course, not every woman approves. Some are uncomfortable with it. Some tolerate it politely. Some absolutely hate the idea. Human beings vary. Relationships vary. Reality rarely conforms to internet mythology.

But yes, there are women who actively encourage it. Some even take charge of it.

There are wives who buy clothes for their husbands. Wives who teach makeup. Wives who insist he coordinate accessories properly before leaving the house. Wives who become unexpectedly invested in whether “that shade really complements your complexion.”

And somewhere in America right now, there is undoubtedly a man standing under unforgiving department-store lighting while his wife says, “You are not buying another black skirt.”

That man probably thought crossdressing would be glamorous. Instead, he accidentally acquired a stylist. Which, when you think about it, may be the most realistic outcome of all.

Wearing Shein

Leon femulates Seka Aleksić on Serbian television’s Your Face Sounds Familiar.