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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 wool or cashmere sweaters because they make a world of difference compared to synthetic fibers.

Quince Alpaca Wool Sweater Green — Baby **Alpaca-Wool Sweater**

Quince Merino Wool Sweater White — Australian **Merino Wool Sweater**

Quince Cashmere Sweater Grey — **Cashmere** Crewneck Sweater

Luckily, Quince offers a wonderful selection of affordable wool and cashmere sweaters. They provide a variety of stylish options at unbeatable prices, all without compromising on quality or comfort. We’ve been longtime fans of Quince for several years now and are happy to see that the brand is finally starting to gain much more recognition for their beautiful, affordable luxury styles. It’s great to find such high-quality pieces that don’t break the bank!

A woman shopping at a convenience store — **Turtleneck** Sweater // **Sling Bag**

Natural fibers are going to feel better in the long run, particularly when the weather fluctuates. 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.

Quince Mongolian Cashmere Fisherman Turtleneck Sweater — Mongolian **Cashmere Turtleneck**

Quince Mongolian Spring Cashmere Oversized Boyfriend Cardigan Sweater — Mongolian Cashmere **Boyfriend Cardigan**

Mongolian Cashmere Shrunken Cable Crewneck Sweater — Mongolian Cashmere **Cable Sweater**

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 pullover sweater and it was the perfect way to look sleek and put together.

Margaret OLeary Elimear Pullover Sweater — **Pullover** Sweater

Bottoms

We pretty much packed jeans for this trip and didn’t wear any dresses or skirts. I (Candy) have been obsessed with Zara’s Marine Straight Jeans and have them in multiple colors. My first pair was a white one that I wore a ton when we were in Paris. I just love the way the high-waist fit combined with the wide leg bottoms makes my legs look longer. Plus, it gives me the perfect chance to show off my favorite shoes in style.

Boyfriend Denim Jeans Distressed — Boyfriend Jeans

Zara no longer sells the exact pair I wore, but plenty of other brands like Quince and Everlane carry very similar styles.

Crystal is a fan of Paige jeans and her recent favorite pair of jeans has been the High-Rise Distressed Boyfriend Jeans. They are perfectly on-trend with a stylish light wash, featuring heavy distressing and a flattering waist. These jeans lean more towards a casual vibe, offering a relaxed, loose fit that’s both comfortable and effortlessly cool.

Quince Bella Wide Leg Pants — Quince **Bella Wide Leg Pants**

Womens Mid Rise Loose Fit Jeans — AGOLDE 90s **Loose Fit Jeans**

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.

Boots

Autumn is such a great time to start wearing boots. Crystal loves her Marcella Knee High Carnegie Boots. They have a chunky platform and are made from 100% Italian leather. It’s very similar to the classic Chelsea boots but revamped with a unique geometric sole.

Loafers

Loafers are making a strong comeback in 2025, becoming a must-have in every wardrobe. They are such a timeless and versatile staple, effortlessly stylish and perfect for both dressing up for a night out or keeping it casual during the day.

Quince Italian Leather Loafer — Quince **Italian Leather Loafer**

I haven’t worn loafers since high school (a staple that complimented my sailor uniform) and couldn’t decide which pair to bring so I ended up packing two pairs that are slightly different in style. The Loraine Tailored Loafers from Sam Edelman were more elegant whereas her Georgia Loafers from Beckett Simonon were more playful. Quince also offers a very similar style at a reduced price, but don’t worry—the quality is still lux. You get the same elegant look and feel without having to spend a fortune. It’s a great option if you want to save some money.

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. I packed a pair of classic high-top Converse sneakers, which is another pair of classic footwear that pretty much goes with anything.

Walking across the street in Japan — Converse **Classic High-Top Sneakers**

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

I wore my 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. I’m a huge fan of Anine Bing but the price point is on the higher end, so I usually wait until their styles go on sale or try to find them used on Poshmark.

For similar blazer styles, I would recommend checking out Anthropologie, Favorite Daughter, and Madewell, to name just a few of my go-to brands that consistently offer stylish and quality options.

Three women posing holding up peace signs — **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!

Anthropologie Patches Houndstooth Blazer

Accessories

Tote Bag

We both used to carry backpacks on our travels, but after our trip to Paris, we’ve been inspired to switch things up and style our outfits with a chic tote bag instead. These days, a lot of brands offer a wide variety of tote bags, so you won’t have any trouble finding different styles and designs that perfectly suit your personal taste. We absolutely love our Nisolo tote bags and find ourselves taking them almost everywhere with us, whether we’re exploring a new city or running everyday errands.

standing in front of a bus stop — **Tote Bag**

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

Sling Bag

There were definitely times when I wanted to be hands-free, and my Lo & Sons Bond Sling Bag proved to be a great option for those moments. This sleek and versatile sling bag can also be worn as a fanny pack, but I personally prefer to wear it over my chest.

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

The black version of this bag is incredibly popular and constantly sells out, so if you’re in a rush to find a similar sling bag, Quince offers a very similar style. Basically, whenever we look for comparable options, our go-to brand has been Quince for great quality and design.

Lo & Sons Waverly 2

We also 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 — **Tote Bag** // MANGO **WIDE-LEG CULOTTES**

She absolutely loves 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).

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).

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