The Middle-Aged Man in Lolita Fashion and His Racing Paper—Freedom to Cross-Dress Has Reached Food Courts Outside the Big City

The other day, I was walking through a busy entertainment district for the first time in a while when I saw a middle-aged man dressed as a woman, singing his heart out at a street karaoke setup.

He seemed completely unconcerned by the people watching him. He carried himself with remarkable confidence.

He stood out somewhat, but he was not loud enough to be a nuisance. He was wearing the clothes he liked and singing the songs he liked. If he was enjoying himself, I supposed that was fine.

Still, I feel as though I have been seeing more people like this lately.

I am not talking about a highly polished presentation in which the wearer could easily be mistaken for a woman. I mean someone who is unmistakably a middle-aged man but dresses like a young woman.

And this is no longer limited to entertainment districts such as Kabukicho or Shibuya.

A Middle-Aged Man in Lolita Fashion at a Regional Shopping Mall

Recently, I traveled to a regional city with a national park to see the autumn colors of the kochia.

Kochia is a plant whose entire round bush turns bright red in autumn. I had gone to see a whole hillside covered in red kochia.

On the way home, I decided to eat at a nearby shopping mall.

And there, I saw someone like that again.

He was unmistakably a middle-aged man, but he was wearing a young woman’s adorable, frilly Lolita-style outfit.

I might have expected it in a major city, but I had not imagined this fashion reaching a regional shopping mall too.

Without appearing concerned about anyone around him, he bought a crepe and sat in a corner of the food court.

He seemed to have come alone.

He was not doing anything in particular. He was simply a middle-aged man in Lolita fashion eating a crepe by himself.

But then came the interesting part.

As he ate the crepe, he unfolded something—and it was a horse-racing newspaper.

His outfit belonged on the fashion streets of Harajuku; the newspaper in his hands belonged at Nakayama Racecourse.

I could not help taking a second look.

Of course, he was free to read a racing paper. He was free to eat a crepe, and he was free to enjoy Lolita fashion.

I simply had never imagined that one person could combine all three at the same time.

His look reflected a girlish aesthetic; his interests were those of a middle-aged racing fan.

Apparently, dressing as a woman does not require changing your hobbies as well.

That is obvious when you think about it, but seeing someone demonstrate it right in front of you makes the point strangely convincing.

And There Is Someone Similar at My Local Station

In fact, I sometimes see someone similar at the station closest to my home.

This person dresses entirely in vivid pink and is immediately recognizable even from a distance.

I used to assume that people who dressed this way gathered only in particular entertainment districts.

But now they can be found in regional shopping malls and at ordinary stations in residential neighborhoods.

If I encounter this many within my own limited range of activity, the world really must have changed.

Then again, they are not causing anyone any trouble.

They eat crepes, read racing papers, and ride trains.

Except for their clothes, everything they do is simply part of an ordinary middle-aged man’s daily life.

Perhaps Freedom Means Not Needing Other People to Understand

When I think about it, I am the one choosing to be surprised. To them, there is probably nothing unusual about any of this.

They wear the clothes they like, eat the food they like, and enjoy the hobbies they like.

They do not need anyone else’s permission.

If anything, there is a certain strength in the confidence with which they ignore the eyes of the people around them.

We live in an era when Matsuko Deluxe—a male television personality known for dressing in women’s clothing—regularly hosts popular television programs and draws strong ratings.

I record one of those shows every week myself. Perhaps what I saw had simply stepped out of the television screen.

That said, I could never find the courage to walk through town dressed that way. I think I would give up at the stage of buying the clothes.

Seen in that light, perhaps they live far more freely than I do.

There is just one thing I still wonder about.

What was the man in Lolita fashion thinking as he read the racing paper?

Was he predicting the next race? Or was he thinking about his outfit for the day?

No, it was surely the horse race.

People may be free to dress however they like, but predicting a winning bet remains as uncontrollable as ever.

In that respect, the world treats every middle-aged man equally.