Winter Packing is always one of my biggest challenges - coats and boots take up so much room in a large suitcase, and packing cubes of jeans and sweaters add up to your allotted 50 pounds shockingly fast (and I could never pack for a winter destination without a checked bag.)

Packing for Japan in winter requires more precision than most cold-weather destinations because the climate is dry, the walking is constant, and indoor heating tends to run warmer than expected. Tokyo, Osaka, and Kyoto typically hover between the high 30s and low 50s Fahrenheit through winter months, yet wind and low humidity intensify the cold, especially at night and in open areas around shrines, rivers, and train platforms. Northern regions such as Hokkaido are regularly below freezing, and the regular snowfall and significantly lower temperatures require heavier layers and well-soled footwear.

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1. Base Layers

The right base keeps you warm and comfortable, even in your cutest outfits - and become absolutely essential in below freezing and snowy areas.

1. Uniqlo Heattech cashmere blend under layers

Uniqlo has been making Heattech for years and years, but I am obsessed with the newer cashmere line - they are so incredibly soft that I started sleeping in the long sleeve shirt every night - I really can't even begin to describe the softness. Wear them on their own with jeans for a simple outfit in warmer areas, and under sweaters and jackets for extra cold. 

The leggings are essential to add warmth to wide leg jeans, which can feel like you're wearing nothing at all when the wind blows (the only time I ever miss skinny jeans)

2. Fleece faux-sheer tights

Not just a TikTok shop ad! (or is that just me?) Fleece tights really do come through and are worth the hype. I bought these ones and was impressed with how warm they were even walking through a blizzarding Sapporo all day. 

If the sheer effect looks too light on your skintone, you can very easily dye them with a little Camel or Cocoa RIT dye - which I did, and they came out absolutely perfect in less than an hour.

3. Nude Tights

OKAY hear me out here - in almost every wintery outfit I put together where I'm in a skirt or dress (and in all of the photos above), my secret weapon is nude tights. I often rewear the exact same dresses and skirts that I wear on warm-weather trips with additional layers, and while a lot of us associate nude tights with grandma pantyhose, especially in photos, the tights read as just skin. While opaque black tights were the standard for so long, they started reading as really dated and basic to me a few years ago, and now I am fully on Team Nude Tights.

I have found that for temperatures above freezing (32 F/ 0 C), standard sheer 30 Denier weight tights are usually enough weight to keep my legs warm while walking around cities and spending a decent amount of time outside. 

I love the shimmery Taylor Swift tights for nights out and dressing up, but for daytime, I have found that nothing is better than Sheertex - the tights billed as indestructible. And so far, I have yet to snag a pair in 3 years of consistent wear. They really are THAT GOOD. The Cappuccino color is the perfect nude for my light/medium tan skin, as I've found other brands can look too pale and unnatural - in every photo you can see my legs, I am wearing these tights. I love that the brand is inclusive and also has shades made for medium and dark skin. 

2. Shoes to Walk 20,000 Steps In

Walking through Tokyo or Kyoto typically means being on your feet all day and walking more than you are used to - but in winter, the streets can be wet, icy, or covered in snow. The last thing you want is to slip and injure yourself halfway through, so I usually go with a solid lug sole for extra grip

1. Platform loafers with socks

A platform loafer with thick scrunched socks is perfect for fashion-forward outfits in Tokyo, cafés, shopping days, or travel days where comfort still matters - and you get a little bit of height in the comfort of a flat. 

2. Dad Sneakers - The Chunkier The Better

Daily default. Comfortable, versatile, and ideal for long exploring days. 

I have never been a sneakers girl - I was trained through my years in New York, and will walk 10 miles in heels, but after a few days, even I needed the comfort of a thick squishy sneaker (Brandon and I both have these same New Balance 9060s), a look that fits in well with style in Japan. 

3. Lug sole boots

A thick rubber-soled boot offers traction and structure for colder or lightly snowy conditions while pairing easily under jeans or shown off with tights.

And if you have room for ONE more... you cannot go wrong with a mid-calf or knee-high platform heel boot.

3. Coats and Jackets

In cold weather, the one item of clothing that everyone sees is your coat, as they cover most of your outfit, or make up the entire top half - but it is hard to fit more than a couple in a suitcase (my best tip is to wear your heaviest and largest coat on to the plane (as well as your heaviest pair of boots!) - coats also make great blankets for long-hauls flights.

1. Oversized Leather Jacket

An oversized leather jacket is current, comfortable, and endlessly wearable - and real leather has an incredible ability to keep you warm in cold and windy temperatures, but not overheat you indoors. If you're still wearing your fitted, cropped leather jacket from a few years ago, maybe look into an oversized style for a modern look that you can fit a sweater or two under (but hold on to your 2010's jacket, the fashion pendulum always swings back eventually). 

For an affordable option, I am obsessed with Quince's oversized leather jackets for a shocking $250 - the quality is top-notch, at an unbeatable price. I also have my eye on this shearling coat - a piece I usually see listed at $1000+ everywhere else. 

2. A statement overcoat 

If you can only bring one overcoat, make it a good one! A structured wool overcoat instantly elevates simple outfits like jeans and sneakers and works everywhere from Tokyo to Kyoto.

3. Puffer Coat

Puffer coats are unbeatable for truly cold days, snow, or northern destinations. Ideal for early mornings, night walks, and outdoor-heavy itineraries.

If you have room for more, add a fuzzy faux-fur cropped jacket to your suitcase!

4. Pants and Bottoms

Japan’s urban layout involves extensive walking, stairs, and public transportation navigation, which requires bottoms that remain comfortable and functional throughout the day.

1. Wide Leg Jeans

Japanese style is currently, the bigger the jeans, the better! I wore jeans on this trip more often than on almost every other trip, denim style just works so well here. Pair them with a tee shirt and a bomber jacket for a warmer, sunny day, or layer with sweaters and your overcoat for colder temps. Just make sure you have some leggings or over-knee socks underneath, as wide-leg denim doesn't keep in warmth very well. 

2. Barrel Leg Jeans

Barrel leg jeans are slightly more fashion-forward and very on-brand for Japan. They add shape to winter outfits and work with everything from loafers to boots. This was one cut I was apprehensive to try and wasn't sure would work on me, but after finding this incredible pair from Lee, I am SOLD.

3. Pleated Mini Skirt

A pleated skirt makes a great nod to the classic Harajuku girl aesthetic - and perfect to pair with tights, loafers and scrunched socks.

A mini skirt paired with a long coat is a timelessly chic look!

If you have more room, round out your outfit options with a fun, colorful or boldly patterened pair of statement pants and a chic wool mini skirt

5. Cold Weather Winter Accessories

Accessories carry winter outfits and make packing feel more varied than it actually is - and are an essential part of staying warm when you're outside for extended periods of time. These items I wore on constant repeat.

1. Fuzzy, oversized earmuffs

Surprisingly practical and very wearable in Japan, especially for night walks and colder mornings. I can be sensitive to getting headaches (I can't wear handbands at all), but I wore this exact pair from Amazon all day without any pressure. 

2. Oversized Scarf

I always forget how much warmth a scarf adds to an outfit - and how quickly you get COLD when you're not wearing one. A thick, oversized blanket scarf goes well with everything, and can be wrapped into a hood with this balaclava hack.

3. Faux-fur hat and/or Headband

faux-fur upgrades a basic hat or headband into a statement piece - and keep you significantly warmer in cold temperatures.

4. Gloves or (even better) Flip Mittens

I have a habit of forgetting to pack gloves, but the difference in warmth this one little accessory provides is IMMENSE. But, I am constantly taking them off every couple of minutes to use my phone (because we all know that even tech finger gloves are very clumsy on a touchscreen). 

This time I got flip mittens - warm gloves that stay on up to the last knuckles of your fingertips, with mitten tops that flip over, so you can pop your fingers and thumb out without needing to take your gloves off completely - what a game changer. 

 5. Convertible Bag For Double Duty Use

One of my favorite packing hacks - one bag that can be worn crossbody and functional for daytime, and as a chic shoulder bag for evening. I'm obsessed with this Prada 2005 reissue Nylon bag, but you can easily achieve the same effect by adding on a simple but bold woven strap to a lightweight shoulder bag.