20+ Cute Tokyo Outfits You'll Be Obsessed With This Year

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So, Tokyo… I swear, you could people-watch there all day and never get bored. The style’s just… fun.

You’ve got sleek all-black outfits right next to neon streetwear, and somehow both look amazing. Last time I went, I thought I’d wear all these “planned” outfits – ended up living in the same sneakers and layering the same two jackets. Oh, and bring layers. Seriously. The weather’s sneaky.

Here are my absolute favorite Tokyo outfits I’m completely obsessed with atm and I’m sure you’ll love them just as much as I do!

20+ Cute Tokyo Outfits You’ll Love

Pink Oversized Tee with Pleated Grey Mini Skirt

This pink oversized tee with a pleated grey mini skirt is a playful pick for a Harajuku stroll, paired with sneakers for urban chic.

Cute Y2k Mini Dress with Chucks

Case in point: a Y2K mini dress with Chucks is a bold choice for Shibuya shopping, paired with a crossbody bag for retro flair.

White Button-Down Shirt with Wide Leg Jeans

Picture a white button-down shirt with wide-leg jeans for a sleek look perfect for a Tokyo café stop, paired with loafers and a tote.

Red Leather Jacket with Midi Denim Skirt

This red leather jacket with a midi denim skirt is a vibrant pick for rooftop drinks, paired with boots.

Blue Button-Down Shirt with Navy Jeans

A blue button-down shirt with navy jeans is a timeless combo for a Ginza gallery visit, paired with sneakers.

Yellow Tokyo Shirt with Denim Shorts

This yellow Tokyo shirt with denim shorts is a sunny pick for a Shibuya street snap, paired with sunglasses for bold vibes.

Yellow Jersey Tee with White Mini Skirt

Case in point: a yellow jersey tee with a white mini skirt is a fresh choice for a Harajuku café hop, paired with sneakers.

Red Leather Jacket with Red Mini Skirt and Boots

Picture a red leather jacket with a red mini skirt and boots for a fierce look perfect for a Tokyo night out, paired with gold earrings.

Oversized Black Blazer with Black Mini Skirt

This oversized black blazer with a black mini skirt is a sleek pick for a Roppongi art gallery, paired with loafers.

Red T-Shirt with Mini Black Skirt

A red t-shirt with a mini black skirt is a bold combo for a Shibuya street stroll, paired with sneakers for effortless cool.

White Mini Skirt with White Jersey Tee

This white mini skirt with a white jersey tee is a crisp pick for a Tokyo park picnic, paired with sandals and a tote bag.

White Button-Down Shirt with Mini Black Skirt

Case in point: a white button-down shirt with a mini black skirt is a chic choice for a Ginza shopping day, paired with a crossbody bag.

Beige Vest Top with Mini White Shorts

Picture a beige vest top with mini white shorts for a fresh look perfect for a Harajuku street snap, paired with sneakers.

All Black Everything Outfit with Black Top and Jeans

This all-black outfit with a black top and jeans is a sleek pick for a Tokyo rooftop bar, paired with boots for urban edge.

Oversized White Tee with Mini Grey Skirt

An oversized white tee with a mini grey skirt is a relaxed combo for a Shibuya café stop, paired with sneakers for easy style.

All White Everything Outfit with Crop Top

This all-white outfit with a crop top is a fresh pick for a Tokyo street festival, paired with sandals for minimalist chic.

Baggy Jeans with Jersey T-Shirt

Picture baggy jeans with a jersey t-shirt for a cool look perfect for a Harajuku shopping spree, paired with a crossbody bag.

FAQ:

How should you dress in Tokyo?

Comfy but not sloppy. Like, jeans and a nice jacket? Perfect. I saw so many people in sneakers – but clean ones.

Throw in a scarf if it’s chilly. And layers, always layers.

Are jeans ok in Tokyo?

Oh yeah, totally. Just skip the ones with giant holes.

I wore mine with a blazer and felt totally fine in Ginza – which is, you know, the fancy bit.

Are you allowed to wear shorts in Tokyo?

Yep. Especially when it’s hot.

But you’ll see a lot more longer shorts and skirts on women. Not a rule, just what’s common.

What is the dress code for restaurants in Japan?

Depends. Ramen bar? Wear whatever.

Nice sushi spot? Step it up – smart casual at least. I once walked into a fancier place in jeans and a silk shirt, and it was fine, but I was glad I’d made an effort.

Where do people dress up in Tokyo?

Harajuku’s where you go bold. Shibuya’s all trends. Ginza’s the place for designer everything.

Oh, and department store rooftops – random, but you’ll spot some seriously cool outfits there.

20+ Cute Tokyo Outfits You’ll Be Obsessed With This Year

20+ Cute Tokyo Outfits You’ll Love