What to Wear and Pack for Japan in May
/This post contains affiliate links, which means that at no additional cost to you if you click on one of the product links, we may earn a commission.
Our family resides in Japan, so we always make it a priority to visit them every year. This year, we visited in the beginning of May. During our stay, we encountered some light showers, but for the most part, the temperatures were quite pleasant, hovering in the 70s during the day. However, at night, it became a bit chilly, dipping down into the mid 50s to the 60s.
Here is a detailed look at what we wore and what we packed for our trip to Tokyo from May 7 - 11.
Day 1 Outfit
On our very first day in Japan, we were traveling from Narita to the district of Shinjuku via train, so we made sure to dress comfortably for the trip. We absolutely love riding the efficient and well-organized trains in Japan, and we try to travel during non-peak hours to ensure that we can sit down and relax for most of our journey.
CRYSTAL
I wore my Express black shorts and paired them with tights and a trendy T-shirt from the brand Mo & Co. This particular brand is quite new to me. I discovered it recently through Instagram, and they describe their unique style as “Smart, rock-chic style.” Interestingly, it turns out that Mo & Co. is a popular fashion staple in China, and their most recent muse for the highly anticipated Summer 2025 collection was none other than the stunning Kendall Jenner.
Since it was a tad chilly at times during our outing, I also decided to layer up a bit and wore my cozy oversized black denim jacket from Anthropologie’s Pilcro line for some extra warmth. To complete my look, I decided to wear my new favorite Dr. Martens 1460 W boots, which I absolutely adore.
I've always wanted to own a pair of Dr. Martens ever since my high school days, and after many years of longing, I finally made it happen. Thankfully, they proved to be comfortable enough for me to wear all day while exploring the streets of Tokyo. Comfy footwear is an absolute must when I'm planning to be on my feet for long stretches of time, and I can happily say that the Doc Martens worked out wonderfully for my adventures.
CANDY
My first outfit was a classic denim and t-shirt look. I wore my favorite pair of J.Crew denim trousers and a cotton scoop neck T-shirt from Quince. I’ve had the J.Crew denim for a few seasons now, and I find myself reaching for them on almost every one of my recent trips because they work so well with various styles.
The trousers feature a super high-rise design, which is a requisite for me, and they also include a comfortable touch of stretch. I’ve always been a long-time fan of a simple tee, and I got the white Quince tees in a three-pack bundle, which saved me 20%. The cotton blend fabric is not only super soft and stretchy but also wrinkle resistant, making it a perfect choice for traveling.
Since the T-shirt is on the lighter side, I decided to layer it with a cozy quilted bomber jacket from Mint Velvet that added just the right touch of warmth and style. For my footwear, I opted for my trusted Adidas Samba shoes that have never let me down. Thanks to their remarkable versatility, they can be worn with pretty much anything in my wardrobe.
Day 2 Outfit
Day two turned out to be another day filled with a lot of walking, and we had the entire day ahead of us to explore the district of Ikebukuro. With the forecast predicting a chance of rain, we made sure to dress accordingly, opting for comfortable yet stylish clothing that would keep us dry if it started to rain.
CANDY
I decided to wear another Quince T-shirt from my three-pack collection and paired it with my high-waisted cropped jeans from Aritzia. I specifically chose to sport a cropped pair of pants just in case it decided to rain because wearing my long wide-leg jeans could result in them getting wet at the bottoms if rain did fall.
Anytime rain is in the forecast, I always make sure to pack a my trench coat. My go-to for years has been my classic Anine Bing trench coat, which will likely remain a staple in my collection for many more years to come. For footwear, I opted for my Michaela Mary Janes from Sam Edelman. I absolutely adore the Mary Jane style and think it’s so sweet and charming.
The leather on these beauties is delightfully soft, which means they tend to scuff more easily than other types of leather shoes I own. Because my Mary Janes have a lower cut, I make sure to wear my Sheec socks with them.
These socks are crafted perfectly for low-cut shoes like loafers and Mary Janes, and they’ve been thoughtfully designed to ensure they won’t slip off my feet. At first, I was a bit skeptical about this feature, but after wearing them all around Tokyo without any issues, I can confidently say that they truly do stay put, and I never once had to bend down and readjust my socks.
CRYSTAL
I wore a super cute mini dress from a unique brand called Disturbia, which is yet another new brand I discovered through my Instagram feed. I must admit, my algorithm seems to know what styles and aesthetics I go for. Kinda scary but I embrace it.
wore a packable rain jacket in the mornings for the cooler weather
At first glance, the pattern on the dress may seem like a simple floral design, but if you look closer, you’ll notice that it’s actually an intricate tapestry of beautiful florals, moths, and skeletons intertwined. It’s such an unexpected combination that adds a romantic yet gothic sophistication to the overall look.
Standing at 5’9”, I find that the dress is on the shorter side for my height, so I definitely need to wear tights with it so it doesn’t look so short on me. To complete the look, I styled the dress with my trusty Dr. Martens boots for a bit of edge, and when the temperature dropped just a tad, I threw on my packable rain jacket. Having that wrinkle-resistant jacket on hand really came in handy for navigating the fluctuating weather conditions throughout the day.
Day 3 Outfit
On day three of our adventure, we dedicated it to exploring Shibuya. The weather was quite overcast, but there were also lovely moments of sunshine breaking through occasionally. Luckily, no rain was in the forecast on this day.
CRYSTAL
I initially had plans to wear my new Mo & Co Tie Details shirt. However, I ended up choosing a shirt that I purchased during our shopping trip in Ikebukuro just the day before. The top is from a charming Japanese fashion brand called axes femme. This brand caught my attention thanks to their feminine European vintage aesthetic that draws inspiration from various eras.
I picked out an eye-catching blouse adorned with a statement ribbon, which featured eyelets and stylish chains that added a touch of flair. Luckily, my favorite black shorts, comfy tights, and sturdy Dr. Martens matched perfectly with my new top, creating a cohesive look. As I wore it, I felt like an anime character infused with a hint of punk fashion.
Candy and I both adore the large ribbon and the lovely crown motif charm that dangles at the end of the chain, which adds an extra whimsical touch to the ensemble. At the store, I noticed the top was styled with a chic capelet and an asymmetric flared midi skirt, which only made me appreciate it more. I did end up purchasing the capelet as well, but I decided to save that gorgeous piece for another occasion when I could truly showcase it.
CANDY
I wore a different pair of J.Crew denim that had a slightly different design and color. The Sailor Denim Trousers 1996 have a lovely high-rise fit, just like my other pair, but they also include two pockets in the front that add a fun detail. This particular pair of denim is darker in shade, giving it a more sophisticated vibe, and they are a bit more stretchy than my other pair, which provides added comfort during long outings.
On top, I chose to wear a fitted ribbed top from H&M that perfectly complemented the jeans. I was immediately drawn to this top for its adorable sweetheart neckline, which adds a touch of femininity to the overall look. However, the neckline does make it a bit tricky to wear a typical bra with straps, so I opted for a strapless bra from Gatherall instead.
Gatherall is a reusable and washable adhesive silicone bra that offers a comfortable strapless and backless solution. Unlike other adhesive bras that I have tried in the past, Gatherall really stands out by providing long-lasting wear without irritating my skin. Plus, it has been incredibly easy to wash and conveniently store after each use, which I really appreciate.
To complete my outfit, I reached for my favorite cardigan from Quince, which has secured its place as a staple piece in my wardrobe. This beautiful baby alpaca-wool cardigan has a flattering cropped length and is extremely lightweight, making it so easy to toss into my tote bag whenever I'm not wearing it. I also decided to wear my favorite Mary Janes again.
Day 4 Outfit
On our last day in Tokyo, we spent the majority of our time exploring the district of Shinjuku before we eventually made our way back to Narita for our departure.
CRYSTAL
I decided to wear my beautiful silk short sleeve top from Quince, which has become one of my favorite wardrobe staples, and paired it with a pretied zipper tie to add a touch of flair. If you haven’t noticed by now, I’m absolutely obsessed with styling my button-down tops with ties these days.
I have no idea how to tie a tie, so I bought a tie on Amazon that I can easily adjust with a convenient pre-tied zipper mechanism. To complete the look with the silk top, I chose to wear my playful yet polished skort from Anthropologie.
This adorable tweed skort is on the shorter side, so I made sure to wear my tights underneath and, of course, chose my iconic Doc Martens to add some edge. These versatile Doc Martens matched seamlessly with all my outfits, and they were the only pair of shoes I decided to pack for my trip, which ultimately proved to be an excellent decision for both comfort and style.
CANDY
On my last day, I pretty much repeated a lot of the favorite pieces I had already worn during my trip, and I made just a few simple adjustments by changing up my top. I wore a Ramones T-shirt paired with my Artizia high-waisted jeans, creating a comfortable look. To complete my outfit, I styled it with my trench coat and my adidas Samba shoes, perfect for a day of wandering.
I’ve never shared the pajamas I wear when I’m traveling, and it’s definitely something I always make sure to pack on my trips. I wore to bed my new PrintFresh Fancy Cat PJ set, which features a very bold and eye-catching print. The set comes with a lovely robe, which wasn’t really necessary to pack, but since I had room for it in my suitcase, I decided to go ahead and bring it along.
I was drawn to these pajamas not only for the unique and playful print, but I also loved the designs cropped top and high-rise pants with pockets. The pajama set and matching robe are crafted from a breathable Eco Satin material, which felt incredibly soft and had such a lovely touch against the skin, making it perfect for a relaxing night in after a long day of sightseeing.
Accessories
We both chose to take our Madewell zip-top medium transport tote bag. This bag is not only made from durable leather that ages well, but it’s spacious enough to hold all of our essentials. Our favorite feature is the zip closure, which keeps our contents secure. It’s not often that we find a tote bag with a zipper.
Quince Suitcase and Lo & Sons Melrose Backpack
We also can’t go anywhere without our Bandolier straps. This handy tech accessory helps keep our hands free and our phone within easy reach at all times. This is the one accessory that we have taken on all of our trips for the past six years.
For our travel necessities, we both used our Quince carry-on suitcases and Lo & Sons Backpacks. Having these travel luggages made traveling through the bustling city and train stations of Tokyo go so much easier.
One last thing…
We wanted to mention that after we left Tokyo, we spent the remainder of our time in our hometown of Narita, where the weather changed drastically for us.
From May 12 to May 16, we enjoyed sunny skies and temperatures that were about 10 degrees warmer than what it was the week prior. This experience just goes to show how much the weather can shift in just a week, so it’s always best to check the weather conditions before you start packing your bags.
