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. As Amazon Associates, we earn from qualifying purchases.

October is Japan’s Fall season and it’s a great time to visit. Although a little unpredictable, the weather is generally mild and pleasant. Temperatures average between 55°F to 65°F (13°C to 18°C).

We like to plan our outfits ahead of our trip and the weather kept on fluctuating from warm to mild, to rain, so this made it a bit challenging to pack since we had to keep in mind the possible fluctuations in weather.

Sisters standing in front of a K car — Wearing Fall outfits in the middle of October in Japan

In October, long-sleeved shirts or lightweight sweaters are ideal for sunny afternoons. For chillier days, a light coat will keep you cozy and comfortable. Dresses and skirts are definitely doable, but it’s a good idea to pack a pair of stockings just in case the temperatures drop.

Here is what we ended up wearing during our two-week trip from October 4th through October 18th.

Tops

Most of the mornings and evenings were chilly and the afternoons were typically mild. On most days, wearing a sweater without a coat kept us comfortable and cozy. For sweaters, we recommend investing in merino wool (thinner and softer than wool) or cashmere sweaters because they make a world of difference compared to synthetic fibers.

Merino Wool Sweaters

A woman shopping at a convenience store — **Margaret O’Leary** Cashmere Sweater // **Lo & Sons** Bond Sling Bag

Natural fibers are going to feel better in the long run, particularly when the weather fluctuates. Merino wool will help you feel warmer in cold weather and when it’s warm outside, it transports sweat quickly away from the skin, helping to keep you cool and dry.

Cashmere Sweaters

Amazon JENNIE LIU Women's 100% Pure Cashmere Sweater

Amazon JENNIE LIU Women's 100% Pure Cashmere Long Sleeve Crew Neck Sweater

Margaret OLeary Elimear Pullover Sweater — **Margaret O’Leary’s** Elimear Pullover

Recently, we’ve been noticing a trend to wear a collared shirt under a sweater (or sweatshirt), so we gave that a try. Crystal wore a collared shirt underneath her Margaret O’Leary’s Elimear Pullover and it was the perfect way to look sleek and put together.

Bottoms

We pretty much packed jeans for this trip and didn’t wear any dresses or skirts. Candy has been obsessed with Zara’s Marine Straight Jeans and has them in multiple colors. Her first pair was a white one that she wore a ton when we were in Paris earlier this summer.

Walking with a cup of coffee — MANGO **Wide-LeG CULOTTES**

Standing in front of a Japanese post box — MANGO **Straight Jeans with Slits**

They are the perfect high rise and the power stretch fabric makes them ultra comfy. The stretch hugs the body in all the right places and the high rise gives the illusion of longer legs.

Walking in the suburbs of Japan — **Margaret O’Leary** Painted Stripe Cardigan // **Daze Denim** Boyfriend Jeans

Crystal is a fan of Paige jeans, but her recent favorite pair of jeans has been High-Rise Distressed Boyfriend Jeans by Daze. They are on-trend with a light wash, heavy distressing, and a high waist. They are also slightly stretchy which makes this denim comfy for all-day wear.

Bottoms

Footwear

You’ll be doing a ton of walking, so comfy shoes are a must. Forget hailing a cab or ordering an Uber because those are your least convenient options (and expensive) for traveling around Japan.

Nisolo Boots

We both packed a few pairs of footwear and the one thing they all have in common is little to no heels. Autumn is such a great time to start wearing boots, so we both brought a pair from Nisolo.

They carry a variety of boot styles and we chose to wear the All-Weather Amalia Boot and the Carmen Chelsea Boot. The quality of both boots is superb, as well as, comfy and versatile. You can receive 20% off your order at Nisolo.com with our code TRAVELPOCKETS20.

A woman in front of a vending machine — Nisolo **All-Weather Amalia Boot**

Walking across the street in Japan — **Nisolo** Carmen Chelsea Boot

Cole Haan Crosscourt Sneakers

For the warmer days, Crystal mainly wore her Cole Haan Crosscourt Sneakers which have been a staple in her wardrobe for a few years now. They are lightweight, comfy, and practically match everything.

Walking in front of a bakery — White Cole Haan **Crosscourt Sneakers**

Three women walking down a neighborhood — Anine Bing **Kaia Blazer**

Sam Edelman Loraine Tailored Loafers

Candy hasn’t worn loafers since high school (an iconic staple that complimented her sailor uniform), but after seeing them everywhere in recent ads, she finally caved in and purchased a pair of Loraine Tailored Loafers from Sam Edelman.

walking and holding a cup of coffee — Sam Edelman **Loraine Tailored Loafers**

three sisters walking and laughing — MANGO **WIDE-LEG CULOTTES**

These loafers were perfect for Japan. The leather is soft and they can effortlessly be styled with any outfit. They look great with a pair of jeans and you can easily coordinate them with a pencil skirt for a more elegant look.

Footwear

Outerwear

We both brought a few blazer options as light outerwear, but for the mornings and evenings, something a little bit heavier was ideal. We didn’t need a winter coat, but something in between was perfect.

Sisters walking and laughing — Anine Bing **Kaia Blazer** // **Margaret O’Leary** Painted Stripe Cardigan

Blazer

Candy wore her Anine Bing Kaia Blazer which was the perfect in-between blazer. Although the Kaia Blazer is advertised as a blazer, I would say it’s more like a jacket because it’s thick and heavy compared to a normal blazer. Candy is a huge fan of Anine Bing but the price point is on the higher end, so she often likes to purchase Anine Bing at a discount from Poshmark.

Three women posing holding up peace signs — Mango **Trench Coat**

standing in front narita's mascot — The Drop **Noa Trench Coat**

Trench Coat

Another coat that we both wore that really came in handy on gloomy rainy days was our trench coat. It’s the perfect transitional layering piece; warm, but not too heavy, ideal for those brisk autumn days. Not only is the trench the perfect layering piece, but it’s also classic, versatile, and oh-so chic!

Outerwear

Accessories

Nisolo Lori Tote

We both typically carry bookbags, but after our recent trip to Paris, we’ve been inspired to style our outfits with a tote bag. The Lori Tote is Nisolo’s best-selling bag and it was perfect for Japan because we can toss just about anything in it.

standing in front of a bus stop — **Nisolo** Lori Tote - Get 20% Off with Code **TRAVELPOCKETS20**

walking into saizeriya restaurant — Cole Haan **Crosscourt Sneakers**

If you’re looking to make your wardrobe more versatile and interesting, tote bags are a way to go. They can be used as a fashion statement and be the center of your outfit.

Lo & Sons Bond Sling Bag

There were times when we wanted to be hands-free, and Lo & Sons Bond Sling Bag was a great option. This sleek sling bag can also be worn as a fanny pack and is available in three materials.

wearing a black leather sling bag — Lo & Sons **Bond Sling Bag**

inside a japanese arcade — Bandolier **iPhone Strap**

Candy chose the sheepskin leather and the material is soft and incredibly lightweight. For a sling bag, it surprisingly holds quite a bit of your everyday essentials. It has plenty of compartments to store cards, passports, or even a pair of AirPods, which makes the bag super functional.

Lo & Sons Waverly 2

We brought with us Lo & Sons Waverly 2 bag and gifted it to our little sister who lives in Japan. She is a mom of two, so being hands-free is a necessity.

sisters eating a dango at naritasan — Lo & Sons **Waverly 2** // Lo & Sons **Bond Sling Bag**

walking down omotesando in narita — Nisolo **Tote Bag** // MANGO **WIDE-LEG CULOTTES**

She absolutely loved the minimal design of the Waverly 2, but what she appreciated most was its versatility. It’s a convertible bag so it can be worn four different ways: crossbody, wristlet, shoulder bag, and belt bag (fanny pack).

Accessories

One More Thing

Typhoon season is from June to October, so although rare, it can rain during the month of October. We experienced some rain and the All-weather Amelia Boots definitely came in handy for those wet days.

October is one of the most recommended and popular times to visit Japan and we couldn’t agree more. There are fewer tourists and the mild weather is drier and crisp which is way better than the hot muggy summers (July-August) and the rainy season (June-July).