A Winter Night in Tokyo & the Fashion That Surprised Me

Daniel TJ International Correspondent Tokyo, Japan

As Christmas comes to Japan once again, I had the chance to ask a good friend of mine ~ Nikki who is from America, what she thinks of Christmas in Japan.

This is Nikki's response to my question about food, fashion, and all around feeling of the holiday season:

I always feel a little emotional on Christmas Eve in Tokyo. I don’t know why. Maybe it’s the lights — too bright for winter, too hopeful for a city that pretends it’s not lonely. Or maybe it’s the cold air that makes everything feel sharper, like memories develop more clearly in low temperatures.

Tonight, I wandered through Shibuya after work. I didn’t have any plans, which sounds sad on the surface, but strangely… it wasn’t. There’s something comforting in being alone inside a crowd that’s glowing with neon and seasonal energy.

And of course — the fashion.
God, the fashion hits you first.

Women walking past me in outfits I wouldn’t have had the courage to wear in September, let alone December. Short skirts that swish when the wind blows. Oversized coats over tiny dresses. Boots that click on the pavement like they’re keeping rhythm with the city. Tights that look so thin I can’t believe they’re anything but decorative.

And every year I think the same thing:

“How are they not freezing?”
And then, quietly…
“I wish I had that confidence.”

A Moment That Stayed With Me

I ended up outside the Shibuya Hikarie building, where people line up to take photos in front of the big illuminated trees. A group of women walked by — three friends, maybe early twenties. Their outfits didn’t match, but somehow they coordinated in that effortless Tokyo way. One in a white coat over a gemstone-green skirt. One in a deep wine-red dress with a faux-fur shawl. The last in black — short skirt, long boots, hair tied in a loose, holiday-style ponytail.

They looked like they were frozen at the edge of laughter.

And I don’t know why, but watching them made my chest ache a little.
Not out of jealousy.
Out of… nostalgia?

Like I was remembering a version of myself that dressed fearlessly once, long before I learned to pick comfort immediately over style. Before I got older. Before practicality wrapped itself around my choices.

Everyone Was Cold, but No One Seemed to Mind

One of the girls did this little shiver — the kind you can’t hide — and her friend teased her for it. She swatted her arm and said something like:

“It’s Christmas! You have to dress up!”

And she meant it.
That’s the thing about Tokyo nightlife fashion during the holidays — it’s not about being warm. It’s about belonging to a moment.

The lights. The music leaking from bars. The couples holding hands. The smell of roasted sweet potatoes mixing with cigarette smoke. Everything feels alive. You dress to match that electricity, not the weather.

I kind of love that.

Later, in Shinjuku — Another Flash of Memory

I took the Yamanote Line to Shinjuku. Don’t ask me why. I just wanted to keep moving. Sometimes the train feels like the only warm place in the city during December.

Kabukichō was its usual loud, messy, brilliant self. People dressed like they were going to 10 different kinds of parties — and maybe they were. Host boys in sharp coats. Women in winter outfits that somehow look simultaneously cozy and bold. Sequins, boots, velvet, tiny bags, red lipstick.

I watched a woman cross in front of me wearing a beige coat open over a tiny holiday dress, legs bare except for stockings. She looked cold, but she also looked… happy. Radiant. Like she was starring in her own music video.

And I thought:

“Maybe Tokyo gives people the courage to dress the way they want.”

It definitely gives people permission.

A Confession I Haven’t Said Out Loud

Sometimes I envy that kind of bravery.

Not the clothes — not exactly — but the spirit behind them. The quiet defiance. The decision to say:

“I’m dressing for me tonight.”

There’s something deeply human in that.

Maybe that’s why winter fashion hits me harder than summer fashion. In the summer, everyone looks good easily. In winter, you have to choose it. You have to sacrifice warmth, comfort, logic. You have to commit.

And that commitment… it’s emotional.

Midnight at the Crossing

I ended up back at Shibuya Crossing, standing there as the screens flashed advertisements and the crowds swarmed in waves. A group of women wearing matching Santa-themed outfits (yes, that’s a real thing — they love it here around Christmas nightlife) began posing for photos. Short red skirts, fluffy trim, sparkly makeup.

They were cold.
I could see they were cold.

But they were laughing so much that I don’t think any of them cared.

And I suddenly felt included in a moment I wasn’t a part of.
That’s Tokyo for you — you can be alone but never emotionally isolated.

A Soft Realization on the Walk Home

As I made my way back toward my station, hands shoved deep into my pockets, scarf wrapped up to my nose, I realized something:

What I used to interpret as “attention-seeking fashion” in winter isn’t about attention at all.

It’s about celebration.
It’s about youthful bravado — or even adult bravado.
It’s about participating in the season.
It’s about beauty over logic, confidence over caution, mood over temperature.
It’s about making your own warmth out of joy.

Tokyo nightlife does that to people. It convinces them to sparkle a little harder.

And there’s something strangely beautiful about a city full of people who are freezing… but glowing anyway.

Merry Christmas! Love XXXXX Nikki

HAVE YOU SEEN THIS? What do Japanese do on Christmas?^