If you’re a dedicated reader of the Best Buy Plug-In Blog, you likely caught my recent post about how much fits in summer carry on luggage. But what about winter carry on, when your clothes are bulkier and your accessories are bigger?

Well, you can still fit a lot into a winter carry on, as long as you pack smart. And, while the items you’ll be bringing along with you will vary, the principles remain the same.

Keep dressing in layers

As I mentioned in my summer packing post, it’s absolutely vital to pack layers when all you’ll be taking with you is a piece of carry on. Especially in the winter, packing items that will allow you to dress in layers will cut down on the number of items you need overall, while still keeping you warm.

My winter carry on looks a little different from most, because I own almost no long sleeve shirts. I just can’t stand them–they feel so restrictive along my arms, so I usually opt for a t-shirt and a wool sweater instead! As you read this post, make sure to update it as necessary for your wardrobe, whether that means adding in sweater vests instead of sweaters, or taking along long sleeved t-shirts instead of short sleeve ones.

For a 1-2 week trip, I would pack two pairs of pants, a few versatile shirts, and a mound of sweaters: you’ll notice in this video that I’ve packed one chunky knit pullover alongside two thin, warm wool sweaters. I love merino wool sweaters because of how simple and versatile they are, but they really shine when it comes to packing. Because they’re so slim-fitting, they take up almost no suitcase space but offer just as much warmth as a chunky lambswool, provided that they’re a fine enough knit.


Outside of packing, they’re a favourite of mine because a high-quality merino wool will last for years. Cotton, modal, and even cashmere will begin showing signs of wear after 1-2 seasons, but merino holds up. I own merino wool sweaters that I’ve had since high school that still look brand new, making them a great option for both packing light and reducing consumer waste.

When you get dressed on your winter vacation, simply layer the items at your disposal. Take a light t-shirt and throw a cardigan on top, or add volume if you have outdoor sightseeing planned. Layer yesterday’s tee underneath today’s knit sweater, and add a scarf before you head out the door.

As you pack, keep in mind the activities that you have planned, too. You’ll need a different outfit for a night on the town than you would for a winter forest walk. Consider packing a casual suit or dress for the former; a pair of long johns or snow pants for the latter. But from the other side of things, let your packing guide your trip, too. If you’re not sure if you’ll have time for a romantic art gallery date while you’re abroad, pack the perfect outfit for it anyways–if you have it with you, you really won’t have an excuse not to make the trip.

Layer your suitcase like a cake

Even though it’s winter, you still need to be packing up your suitcase like it’s the most delicious cake you’ll ever eat. (In other words, pack in layers, and make sure they’re distinct.)

Roll each small item of clothing into an organizer, and fill up any excess space with necessities like socks and underwear. Bring long johns and wool socks instead of an old pair of shorts for sleeping in, and don’t forget essentials like tweezers and a toothbrush.

Pack bigger items on their own and secure firmly. If you watch the video in this post, you’ll notice that I zipped a chunky sweater into the top of my winter carry on alongside my cosmetics bag, and fit a few pairs of pants and a scarf into the bottom half with my ripstop packing cube.

Don’t forget your winter woolies!

When it comes to packing winter carry on, your “don’t forget this!” Task is the opposite of what it would be in the summer. Instead of focusing on sunscreen and bathing suits, make sure you’re dressed appropriately for the weather.

A ski trip would require different accoutrements than a winter city vacation, but both will require a heavy jacket and warm accessories. I like to bring a wool coat with me when I travel (opt for down if you’ll be exploring outside), along with a few different scarves, a hat, below-the-head ear muffs, and smartphone-friendly touchscreen winter gloves.

This video on how to pack winter carry on luggage also includes a little segment on the makeup that I’d bring along for the trip, because let’s be honest: if you’re the kind of person who wears makeup every day, it’s the first thing you plan out when you start packing. I really couldn’t care less which three t-shirts come with me to the mountains, but if you suggest for one second that I should take a highlighter with gold reflects with me instead of a cool-toned pink one, I will laugh you right out of the room.

For a winter trip, I’ve packed some of the same products I took with me for my summer carry on, and a number of new ones. You’ll spot my Clinique Flutter-to-Full Mascara, Make Up For Ever Pro Light Fusion Highlighter, and Clinique x Crayola Lip Colour. For the eyes, I’d bring along just one palette: the new Annabelle Eye & Brow Palette.


If you’re going on a family trip, make sure to pack for the kids, too. They may pack their own toothpaste, but will they remember to put a heavy moisturizer into their winter carry on to guard against chapped skin? Probably not.

I packed all of these winter carry on items into the Swiss Gear Extravagance II Carry On, which is available in a set of 3 expandable, 4 wheeled pieces of luggage. It was my favourite piece of luggage that I’ve ever had the pleasure of testing, and for good reason.


Check out Best Buy’s carry on luggage options and tell us what would you pack for your dream winter vacation?

Rae Chen
Rae Chen covers everything from handbags to speakers here on the Best Buy Plug-in Blog. They can also be found at thenotice.net, where they've been writing about beauty & wellness since 2007.