Winter Outfit Ideas for Tokyo + What I Wore


tokyo fall winter outfits

Hi friend! I recently got back from a trip to Tokyo and Thailand to celebrate my bf’s birthday. Well, if you ask him, it wasn’t a birthday trip. It was a trip we booked over his birthday because he found a great points deal for the flights. But pretty much the same thing, you know?

We had an action-packed four days exploring Shinjuku, Shibuya, and a little bit of Ginza. We ate a lot of great vegan food, did some shopping, and went to some iconic locations. More Tokyo guides are coming for you soon! 

I had so much fun dressing up for this trip to Tokyo. I don’t know about you, but I love dressing up on vacation. When I’m at home, I’m usually in comfy sweats. So, vacations feel like a great opportunity to plan some outfits and get dressed up!

For these Tokyo outfits, I wanted to go with classic edge- a lot of classic styles, mixed with a little bit of edginess. I’ve been trying to overhaul my closet lately and fill it with basics that I wear over and over again. A lot of these pieces are wardrobe basics that you can mix and match in different outfits.

So let’s get to the fall and winter Tokyo outfit ideas! 

Tokyo Outfits: Daytime

tokyo outfits winter

Plaid Blazer

Cropped Turtleneck

Cropped Denim

Vegan Loafers

Vegan Purse


I was going for an elevated classic look with this outfit. The plaid blazer inspired me. Also, I ended up wearing these vegan loafers almost every day of the trip and they were so comfortable. I’m talking 5-10 miles walked every day and I didn’t even have a blister. They’re awesome quality!

Tokyo 2023 Outfits-cropped cardigan long black skirt loafers

Cropped Cardigan

Mushroom Bodysuit

Black Midi Skirt

Vegan Loafers

This outfit was inspired by the super feminine looks I was seeing in the Shinjuku area. A lot of bows in hair and skirts. I didn’t do the bow, but I did bust out this black skirt that is so fun to wear. You can literally twirl in it. 

Tokyo 2023 Outfits-denim maxi skirt winter

Faux Leather Jacket

Black Sweater

Denim Maxi Skirt

Black Tights

Vegan Belt

Vegan Loafers


I am obsessed with the denim skirt trend, so I was so excited to wear this outfit and to include it in thie Tokyo winter outfit ideas roundup. It seems like it might be tricky to style at first, but it’s kind of like styling jeans.

Tokyo 2023 Outfits-plaid blazer cropped jeans

Plaid Blazer

Tan Sweater

Oversized White Button-Down

Cropped Jeans

Vegan Sneakers

Vegan Purse

For this outfit, I wanted to go with the preppy casual vibe. (The plaid blazer really helped out here!) 

Alright, now let’s get to the nighttime Tokyo outfit ideas!

Tokyo Outfits: Nighttime 

Tokyo 2023 Outfits-nighttime date



Nothing like a cutout dress for a date night! I love that this one is a great neutral color too, which is great for the winter.

Tokyo 2023 Outfits-winter date night in city

Waist Tie Top

Wide Leg Racer Jeans

White Boots

Vegan Purse

These have become my favorite jeans of 2023. They are SO soft and just look cool to me. And they were really fun to wear in Tokyo- where so many people just look effortlessly cool.

Tokyo 2023 Outfits-date night at the new york bar in the park hyatt


Faux Leather Jacket

Black Pants

Vegan Boots

Vegan Purse

This is such an easy winter date night look! Grab a pair of black pants, add a corset and a faux leather jacket, and you’ve got a cute winter date outfit. I wore this to go to The New York Bar at the Park Hyatt– which is an iconic spot that was featured in Lost in Translation. I’m working on a guide to Tokyo now, so more on that to come!

I hope this guide gave you some winter outfit ideas for Tokyo. You can check out more outfits in my LTK store. And – lots more Tokyo to come here on the blog too! <3

Xo, Lauren

Check out my Tokyo vlogs here.

Find more travel inspo here.

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