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Smooth Brain by Ali Whittle · Apr 5, 2026

Cool Girls in Real Life: Tokyo

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Ali Whittle · Smooth Brain by Ali Whittle

Hi Friends!

Welcome to a brand new Cool Girls in Real Life edition. This time, the spotlight is on Tokyo.

I just got back from a 9 day solo trip in Tokyo, Japan. It was fabulous.

Tokyo is one of my favourite cities to visit. I first visited two years ago and not a day has gone by where I don’t think about it. Desperate to make another trip happen - I squeezed in a week-and-a-half solo sojourn in March!

The city is so inspiring, so unique, so special. The people are so kind. The food - just so delicious. It feels like they live in the future. I love it.

And the style. The style! Well that’s why you’re reading this.

It’s up there with one of the best-dressed cities in the world - it really has its own distinct look and fashion flavour. It felt like everywhere I looked there was a stylish person - and thankfully I’m very quick to whip out my phone to capture said people - so I can share with you.

I’ve previously showcased the Cool Girls of Stockholm, Paris and Sydney - it’s one of my favourite substack series to put together. Documenting how people get dressed and how it differs from city to city is so fascinating. And as I always say, the coolest thing you can do is to be authentic to yourself - however that looks and feels.

I visited Tokyo at the start of Spring - temperatures were still on the chilly side (my ideal weather scenario). Some style themes I noticed were:

  • Layers! Skirts over pants, thinner jackets under bigger jackets, stockings, gloves!

  • A darker colour palette is the go-to; lots of black, navy, brown.

  • Chunky boots and sneakers

  • Frill/lace/tulle

  • Sports style sunglasses

  • Hats!

  • Big jackets - leather, trench, suede, car coats - all oversized

  • Good denim - a lot of bootcut!

  • Intriguing and unexpected colour combinations - tan and lime, olive green and tomato red.

  • Beloved, well-kept bags

  • Plush toy bag charms

Something I was so inspired by during my time is how accessories are incorporated into everyday style - and the whackier the piece, the better! But it’s not being done in a costume-y way - but rather, it just highlights the wearer’s personality.

So - if you have pieces you are saving for a (stylish) rainy day, try weaving it into a casual outfit day. Fun hats, glasses, bags, gloves, stockings - wear them all more regularly! These pieces clinch the look and keep things interesting.

Note: This substack is a little long - if you’re reading this via your email, it’ll say ‘View Entire Message’ at the bottom - click on that to keep reading, or view the entire newsletter in the Substack app (my preferred way of consuming these).

So, without further ado, here is:

The layering and the mix of textures - plus her wavy, textural hair cut - couldn’t be more obsessed with this diva.
I haven’t stopped thinking about this outfit and the colour combination. Mixing olive green velvet with tomato red was so interesting and eye-catching, I love it so much. Paired with a fantastic bootcut jean and sporty shades!
Another moment for this jacket - it’s just perfect.
Such a cool couple.
Big fan of his Bode jacket and pants.

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She left me speechless - like riding her scooter in this ensemble!?
I love this colour palette and silhouette.
This multi-colour knit dress and the sneakers. Cosy and edgy.
Really fun mix of clashing colours and patterns.
I love to see a well-loved and used Hermes Kelly!
Very cute knit outside the Bode store.
Oversized head-to-toe - I need that jacket.
An excellent double denim moment + the pink beanie clinches the whole look for me.
A masterclass in layering and colour-play. I love the padded jacket and matching skirt - over the jeans takes it to another level.
Tan suede with a lemon lime polo is something I’ll be recreating.
Loved these gals at brunch.
I spotted tulle frills a lot in Tokyo. Loved how she paired it with a grey hoodie with lace.
Perhaps the coolest group of friends
Two excellent coats
This gorgeous couple were so polished and chic.
Such excellent layering, mixing textures and patterns!
I really love red and chocolate brown together - and that fuzzy bag is so fun.
Love this whole look - see below for her very fun hat!
This feathery hat is so unexpected!
Very much enjoyed this couple’s complimentary pink tones.
Love the floral denim and chunky boot combo.
Love the metallic shoes and stocking socks peeking through the blue ribbed pants.
Such a gorgeous cropped collarless leather jacket!
I just really love this hat - such a sleek look.
Love the chunky knit with the pale blue necklace! See his fun fuzzy bucket hat below.
Omg and the penguin backpack!
Such a good blue!
Sporty and chic!
Excellent shoes, perfect oversized leather jacket and cute scrunchie!
I just adore these jeans! (and everything else)
I need this trench.
Thom Browne, an excellent ponytail and a Chanel 25! No notes.
Neeeeed the jacket, need the pants!
We all could take note and add more hair accessories into our daily rotation!
Such a great suede bomber and pleated skirt.
Chunky shoe + big jacket and baggy denim is a real uniform here.
Love his plaid jacket and her stripe dress/denim/jacket combo.
This look made me realise I love navy, red and denim!
Never forget the joy of a red sock!
Bag charms are such an easy/fun way of injecting colour into an outfit!
Rainy day chic.
Love the cute touch of the little sock and heel!
Such a great outfit - layered jewellery, graphic tee, leather blazer, tailored pants and the red cap to tie it all together. Also love the boot shape too!
Boys and their bags! Loewe and Hermes - would happily take these for myself too.
More tulle!
Just a great look - I am always always a sucker for a fab jacket.
Love the Lemaire croissant bag!
Texture! Layers! Love.
Cute turtleneck peeking out of the grey vest.
Such a cool look - love the sheer bandana.
Off to sketch - love the jacket and those shoes!
Great denim cut
Love the ribbon in her hair
I need a green jacket!
Going to have to get myself a blue beanie.

More Smooth Brain Thoughts soon,

Ali xxx

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