Saturday, February 7, 2026

Packing Light for Winter Travel

Packing light can be difficult, and packing light for winter is even more challenging, especially if you don't know what to take with you for what might be a wide range of weather. I have gone on vacation in October-December and had it be so warm that I don't need a coat at all, and also so cold that I wasn't prepared for how cold it would be. 

When packing for winter, making sure you can get everything you need in a carry-on might be quite a challenge. Here's how to do it!

Always assume weather will vary. One year we went to the UK in November and it was 70+ degrees for the first half of our trip. We've also been to France in October and was in the 20s and rainy the whole time. How do you even deal with these kinds of conditions? Layering. On those trips, I both thought I would have to buy some warm-weather clothing and had to wear many layers of clothing to stay warm. You don't always know what you're going to get, so I have learned to choose items that mix-and-match and can also layer over/under each other.

Last week, some friends and I had a staycation crafting night and I took the time before they arrived to make a couple little videos for you. Bonus, I packed my whole wardrobe in my new 16" roller bag, with my laptop and other onboard items I like to have with me in my travel backpack. 



I somehow created what looks like the opening to an 80s sitcom that centers on a woman who pretends to be quintuplets maybe. LOL!

As you can see, it's not that difficult to choose a capsule wardrobe, even for winter travel. 2 pair of pants and 2 pair of shoes can go with a range of tops, while your tops can go individually, or be layered to keep you warmer if needed. You can easily add a dress or skirt to this and have even more options each day. You'll want to bring along some laundry sheets to wash clothes at least once during your trip, if you're going to be gone for a week or more. 

So, let's look at how I packed all of these items, and everything else that was in my bag - with room to spare! - and backpack, so I was able to keep my wardrobe small, but impactful. 


You don't have to use packing cubes either, unless you really just want to be extra organized. This bag is easy to keep things separated and it's not large, so you can find it all quickly. I happen to like to just pull my cubes out and toss right into a drawer, but I actually just threw all these things in my bag at home and didn't put them in cubes until I started repacking for this video. 

As you can see, I packed everything in my first video, plus an extra pair of shoes, underwear, socks, an tank top, pajamas, slipper socks, a base layer top, fleece-lined leggings to go under pants, and most of my toiletries. There is still room in the top compartment for extra necessities, like a bathing suit, lightweight scarf, hat, or a laundry bag/pop-up hamper. 

It allowed me to only have to use my backpack for things I can use on the plane and my laptop, like reading material, an extra cardigan or wrap, liquids bag, snacks, charging cords, and to stash my sling bag for boarding. I'd also be bringing along a reusable water bottle on every trip and probably some jewelry pieces to elevate my outfits a bit when going out to dinner. I'd also "wear" my packable jacket on the plane.

bags I use: Calpak Mini Hue (dragonfruit) | Hedgren Halo (black) | Portland
Gear Standard Cascade Backpack (cherry blossom - above is lavender)

If I can create all these outfits and fit them all inside this small roller bag, which as been my goal for a long time now, you can easily do it with a regular size carry-on. It helps to have the right bag for your trip. I know that I struggle to get a larger bag in the overhead and I need much less than I always think I need. I also like to have sections that can be organized instead of just one big compartment that I just throw things into. You already know that I love my Cascade backpack from Portland Gear. We have two and a tote. I might be in the market for their weekender as well. They just released a full-size carry-on roller bag, too, so if you don't think you can manage a smaller bag, I highly recommend theirs. 

What are your biggest challenges for packing for cold weather?

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