21 Days in Japan in a Carry-on + Outfits

21 Days in Japan in a Carry-on + Outfits

As I post this, we are on the plane headed to Japan—for three weeks! I'm going for two weeks for work in my company's Tokyo office. Luckily, my husband gets to come too, and we get to spend a few vacation days in Kyoto and a few days sightseeing in Tokyo together. Three weeks presented a serious packing challenge... my favorite kind!

Torii Gates in Kyoto photo by Dil on Unsplash

How I decide what to pack

I started my packing list for this trip over a month in advance. That's a little excessive, but the last three weeks have been intense—jam-packed with work and personal events. So I knew I needed to get started as soon as the trip was booked, or I would be throwing together a confusing suitcase the night before.

I always start by making a list of the trip's constraints. Some things I consider when packing:

trip length, events and activities, the weather, culture and any cultural/religious considerations for attire, and inspiration on what locals wear

I don't use an app to track my outfits, just my bullet journal and notes on my computer. For packing lists, I make a document and start taking notes. Pretty low-tech, but it works for me!

My husband and I always check our bags, so the title may be a bit misleading—but I take an international sized carry-on bag and never anything bigger. It's easy to carry, no matter the kind of transport, and I know if I had to carry it on, I could.

Work and the weather

Since this is mostly a work trip, it’s important that my outfits are conservative and professional enough. Japan typically has very conservative workplace attire. Although my company isn’t primarily Japanese, and our Tokyo office is full of developers from all over the world, I still want to look professional, since I’ll be training others.

It's also important to be considerate of cultural norms—in Japan, that's wearing socks (not shoes) inside homes, not showing chest or cleavage, although legs are fine, and covering your tattoos. That last one is going to be tricky, as I have tattoos on my lower arm and right shoulder to my elbow. On one hand, I'm a visitor, but on the other, if I plan to visit sacred sites and temples and go to traditional, nice restaurants, I'll do my best to be respectful. I also made sure not to pack sandals or mules, so that I'd always have socks. (Plus, sandals aren't the best long-walk shoes.)

workspace at the tokyo office from officesnapshots

Because my trip is so long, I need to make sure my options are versatile enough. I like having variety, but I also have a range of activities and weather to pack for! We’ll be sightseeing and walking around a lot outside, and I’ll be walking to the office, so comfort is a big priority. Nothing is worse on vacation than achy, blistered feet, or being way too hot or cold.

The weather in October tends to be around 55-65°F (14-18ºC) at night and in the morning, and 65-75°F (19-23ºC) during the day. Japan is definitely temperate but subtropical, so there’s a good chance it will rain and/or be humid. I need to be prepared for 75°F and sunny walking around outside sightseeing, but also for 55°F rainy mornings, and everything in between!

Finding Inspiration

One of the first things I do when I’m thinking about travel outfits is look for some inspiration! It's the most fun part, but it's also good research. A lot of times when we travel, our destinations aren’t similar to our home in culture or climate. I like seeing how people dress where I’m going, and how they handle the weather.

I did a lot of searching for tips on Japan style and what people say about how to dress. Of course, I also spent plenty of time looking at all the incredible Harajuku street style. Even though it's not my style, it gave me lots of ideas!

I made a Pinterest board for the trip — Tokyo Inspiration. Here's some of my favorite picks that inspired my packing list.

Some key items

After I had a good set of inspiration photos I liked, I looked for patterns. Some key items and proportions stood out:

  • A sporty sneaker
  • A flat, masculine boot
  • A straight dark jean
  • An oversized layer
  • A fitted, solid colored, higher neck top
  • A crossbody or sling bag


  • fitted all over, with an oversized layer
  • fitted bottom, with a boxy, oversized top

Color Palette

black · navy · burgundy · rosewood · olive · cream

Kind of like my blog color palette, hmmm. I may have a look!

Style statement

As I looked at my closet, the weather, and the vibe I want for this trip, I determined a few key “style statements” to help me pack.

cosmopolitan · restrained · versatile · sporty · monochrome
Photo by Manuel Cosentino on Unsplash

cosmopolitan — Tokyo is a big, big city, and fashion ranges from Harajuku street style, to modern, oversized, all-black, Rei Kawakubo and Comme Des Garçons inspired looks, to classic business suits. I wanted to bring a wardrobe that felt modern and big-city. I was inspired to bring some of my boxier, looser shapes because of this.

restrained — I'll be spending most of this trip at work, not sightseeing, so I wanted to be respectful and professional. I don't wear a lot of prints anyway, but I kept my color palette and necklines restrained.

versatile — This might be similar to restrained, but this was a key for me in picking my options. I wanted as many of my tops and bottoms to go together as possible, and even be paired and layered for weather. Even my most colorful items work together and with all my shoes.

sporty — I always opt for a sneaker when I travel, especially for sightseeing. As much as I want to dress up for work, I want the comfort of a hoodie and sneakers. I tried to pick my most "fashion" sporty options, with cosmopolitan shapes. My cropped hoodie will be just as useful with leggings while traveling as it will be with my cream midi skirt for a cold day.

monochrome — I didn't want to bring all black, but lots of my inspiration picks were pretty monochrome: black and navy, all white and cream. My rosy colored items like the turtleneck and shoes can be paired together, and my boots and burgundy top live in the same color family.

What I’m packing

The best advice I ever read about packing for a multi-week trip was: pack for a week! We'll be able to do laundry, too. I tend to have a fairly versatile color palette in my wardrobe anyway, but I tried to leave out some of my brighter or more difficult to pair colors. Making outfits is way easier when everything goes together!

I'll be there 21 days, plus travel. I brought:

9 tops, 7 bottoms, 1 dress, 1 jumpsuit, 3 shoes, 3 outerwear, 2 bags

For a trip of this length, I'm expecting to wear each pair of bottoms 3-4 times, except perhaps my shorts and leggings. With 9 tops, that means each will have to get worn twice. Realistically, some will get worn a lot more (looking at you, white crop tee and Linn tees) and some less, like my grey merino, unless it's quite chilly all day. I ended up bringing more items than I might have, mostly to make sure that I would have a sufficient range for the weather and any activities we do! With only three pairs of shoes, I'll get a week's worth of wear out of each of them — a quarter of the way to 30 wears!


  1. Cotton Citizen white crop "Tokyo" tee (appropriate, huh?)  link, made in US
  2. black raw hem crop tee old, similar (responsible), similar (made in US)
  3. Elizabeth Suzann Linn tee, black linen link, ethical
  4. Elizabeth Suzann Linn tee, navy silk link, ethical
  5. Aritzia green mockneck tee link, (not ethical) similar (responsible)
  6. Rag + Bone navy long sleeve Theo tee past season color, in grey, not ethical, similar (responsible)
  7. Outdoor Voices grey merino mockneck longsleeve tee similar from OV (responsible)
  8. Aritzia bell sleeve burgundy Jolie long sleeve past season, similar short-sleeve, (not ethical)
  9. Kit + Ace rosewood Prevost sleeveless turtleneck past season

I opted for both my Linn tees, because the silk version is so versatile for a nice dinner or a hot day. The burgundy and navy long sleeves were both lighter/mid weight long sleeve options that I might not have otherwise brought, except I wanted to make sure I had choices if I needed to cover my tattoos on a warmer day. The Linn tees and my white crop tee both have longer sleeves, which helps with that, too. The grey merino is for chilly days, so it might not get worn much, but I'll sure be glad to have it if it's cold and wet!


  1. Kit + Ace Seaside cream knit midi skirt past season
  2. Elizabeth Suzann Clyde pants, black cotton canvas link, ethical
  3. Elizabeth Suzann Clyde pants, black linen not pictured, link, ethical
  4. Aritzia olive paper bag shorts link, not ethical
  5. Lululemon Align high rise black leggings link, not ethical similar, (sustainable)
  6. AYR Apache Canyon skinny jeans past season, similar (responsible)
  7. AYR Superba raw hem crop flare jeans link (responsibly made), similar (responsible)

I almost didn't bring shorts, but there's still a good chance of 70-75°F temps at least for a day or two! I get hot easy, so I decided to bring them anyway. And yes...I brought two pairs of Clydes: a cotton and a linen. Again with the weather options!

Leggings double as pajamas/activewear, so I'll be glad to have them even if I don't wear them out much.

Dress/Jumpsuit and Outerwear


  1. Aritzia black henley midi dress past season, similar (not ethical) similar (responsible)
  2. Elizabeth Suzann Mara jumpsuit, black linen link, ethical

I opted for both of these options because they're a little sporty, a little restrained, and super easy to wear. I'm not much for layering in my outfits normally, but these also can be layered over or under most of my top options, which means I have more choices if it's cold, or I want to cover up the lower neckline on these.


  1. Everlane cotton utility jacket link, responsible
  2. Aritzia Quincey black silky trench coat link, not ethical
  3. Aritzia black crop hoodie link, not ethical similar in tan (responsible)

This trench coat might be the item I'm most excited about. I think I can wear this over every single outfit I can put together, and it adds just enough fanciness. It's not very warm, though, so my Everlane utility jacket will be my warm layer. The cropped hoodie is a personal fave; it's sporty but nice for a hoodie, and because of the boxy crop, it feels intentional.

Shoes & Bags


  1. Stella McCartney rose sneakers link, responsible
  2. Joie black snake print low sneakers, secondhand, similar (not ethical)
  3. Freda Salvador Sleek croc chelsea boots link, ethical also in black, black croc

I know... I brought pink sneakers instead of black ones. Trust me, I debated this long and hard. In the end, the Stellas felt more fun, so I think I'll enjoy outfits with them more. They're also super cushy and comfy, so perfect for long sightseeing days. The boots and low sneakers both can be dressed up, but are still comfortable enough to walk around in.


  1. Stowe Evelyn crossbody leather bag, black link, ethical
  2. Dagne Dover nylon sling bag/fanny pack, black link, not ethical
  3. black baseball hat old, similar (responsible)

I could have opted for a single bag, but I like the idea of having a dressy bag for nice events, and the sling bag for sightseeing. I always bring a baseball hat, too, just in case I have a super bad hair day!

Potential Outfits

Next, I went through and made some outfits. I started with the combos I'm most excited about wearing, and then made sure I had outfits for hot weather, cold weather, work, nice dinners, and sightseeing!


For going out to dinners and evenings in the city, I'm picking a lot of fitted or boxy tops and my boots. Definitely going for monochrome and restrained here.

Most excited to wear...

this cream midi skirt and white cropped tee combo; the fitted bottom/boxy top proportions are so interesting with this skirt, because the waist is so high. I love the light monochrome look, too. The green mockneck, Clydes, and boots are a close second favorite though!

Nice / Work

I put together some outfits I'd wear to the office, although the overlap with my going-out city outfits is pretty high. For these outfits I was thinking cosmopolitan and versatile.

Most excited to wear...

the crop flare jeans, linen Linn tee, and boots combo. Same boxy top/fitted bottom proportion, but with interesting pieces and textures. These chelsea boots look so great with the slightly cropped raw hem on these jeans; I love the contrast of the raw hem, faded denim, and shiny croc leather.

Cold Weather

For chillier weather, this mostly means my long sleeve options and utility jacket. But I also tended to pick my skinny jeans versus a cropped length. These outfits are feeling sporty and versatile.

Most excited to wear...

the most boring outfit on here: my grey mockneck merino long sleeve and skinny jeans. I think the rose sneakers and silk trench will make it fun to wear, even if it's just jeans and a tee. The silk trench gives it that fitted with an oversized layer proportion I identified as inspiration, too.

Sightseeing / Warm Weather

For our outdoor sightseeing days, my Stella sneakers show up a lot more, along with shorts and my sling bag. No nice leather bag on these days! Sporty and monochrome — even though there's more color here — is the name of the game for these outfits.

Most excited to wear...

my silk navy Linn tee and olive paper bag shorts. I've worn this outfit a bunch this summer; it's just so comfy and easy, but proportionally interesting. I think the utility jacket will make it even better.

Wrap up

I love a packing list post, they’re probably my favorite style blog to read! I was really excited to make this packing list, and to write this post. I can't wait to share real outfit photos over the next three weeks and report back on what worked for me... or didn't!

Photo by Alex Knight on Unsplash

I love the excitement of traveling somewhere new, mixed with the ability to curate a mini-capsule with a specific vibe. Packing feels like a great puzzle that I love solving. Of course, nothing beats the actual travel itself! Exploring a new place is one of the best experiences you can have, in my opinion. Travel helps us learn how others live; it gives us inspiration, empathy, and an understanding of the world we just can't get at home.

Where are you headed next — and what’s the vibe? Do you try to pack with a specific style in mind?