Packing carry-on luggage for a winter trip usually feels impossible. Cold weather means heavier layers, bulkier clothes and shoes that take up half the suitcase. I used to joke, “If you pack just one sweater…your suitcase is already full!” But with the right strategy, it is completely doable to take on winter travel with a single carry-on.
The key is understanding how winter clothes work and building your wardrobe around one simple idea: your outerwear does most of the work. Most of the time when you’re moving about, you’ll be bundled up and day-to-day people will only see you and your coat. When your coat, hat, gloves and scarf carry the warmth and the style, everything underneath can be lighter, smaller and more strategic.
Here is how to pack smarter for any cold-weather trip.
Start with warmth, not bulk
Winter packing is all about performance pieces, not the size of the stack in your suitcase. A strong base layer keeps your core warm and manages moisture. A mid layer traps heat. A protective outer layer handles wind and snow. Once you think in systems instead of outfits, the number of items you truly need drops fast.
For example, for a five day trip, I can usually get away with just two pairs of warm pants. Jeans and a pair of corduroys; plus the travel pants I wore on the plane, whether leggings, cargo pants or sweats. I will also bring two warm base layers, rotating them to let each air out between wears. Two or three sweaters covers everything from casual days and nicer dinners. Cashmere is especially useful because it delivers warmth in a thin layer and saves valuable space.
With these pieces working under a solid winter coat, you stay warm without packing your entire closet.
Commit to a single color story
A limited color palette is one of the easiest ways I keep winter packing under control. When everything coordinates, I get more outfits from fewer pieces. I usually build around black, charcoal, chocolate or warm neutrals because they hide wear, stay polished and mix effortlessly. But I’m also not afraid of one bold pop, like kelly green or yellow, to keep my winter outfits from feeling flat.
The accessories follow the same plan. One scarf, one hat, one pair of gloves. When the colors already match what you packed, you never feel like you need backups. It is a simple trick, but it stops me from adding “just in case” pieces that only take up space.
Why you should not wear your bulk on the plane
I’m not a fan of the old advice to wear your biggest coat and heaviest boots on the plane. Who wants to feel uncomfortable wearing all of your biggest things while going through security and then sitting on a plane for hours! It makes the airport experience stressful instead of smart.
It’s easy enough to just carry your coat. Most airlines aren’t counting your coat as an additional personal item. So carry it in hand and store it once your board the flight (and all other luggage is in the overhead cabin). One of my favorite packing tricks is if the coat has a large hood, I fold the body of the jacket into it and turn it into a soft pillow for the flight.
Wear one main winter shoe, pack small problem solvers
Shoes can be the downfall of winter packing because they are bulky and heavy. I stick to one main pair that I wear during travel days. If I know I will be walking through snow or slush, I wear a warm, traction-heavy boot. If it is a cold but dry destination, I wear a comfortable sneaker. Either way, the pair I choose is the one I rely on the most.
Then I allow myself two small additions. I always bring flip flops for hotel rooms because I never walk barefoot on those floors, and they weigh almost nothing. If I expect a nicer dinner or night out, I pack a lightweight dress shoe or a slimmer sneaker that fits flat in the suitcase. These pieces solve specific problems without adding bulk, and the main winter shoe does the heavy lifting.
Go compact with accessories
My travel jewelry is simple because I do not switch pieces on the road. I wear small huggie-hoop earrings that stay in for the entire trip and a Garmin watch because I like to track activity. That is usually it.
The real accessories are the cold-weather ones. Believe me, you can get away with just one warm hat or beanie, sometimes two if the trip is long. One scarf and one pair of gloves. The type depends on the destination. Ski trip means heavy-duty insulation. City trip means something lighter but still warm. These choices matter because people rarely see your outfit under a winter coat. No one is judging you because you keep wearing that yellow beanie. They will only know you are wearing that yellow beanie to find you in the crowd!
Edit ruthlessly
Winter packing works only when you are intentional. Before anything goes into my bag, I ask myself two questions.
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Will I wear this more than once?
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Does it solve a weather problem?
If the answer is no, it stays home.
I do not pack “just in case” items. Instead, I match my clothing to my actual itinerary. This keeps the bag lighter and ensures I use everything I bring. It is a small mindset shift, but it eliminates half the unnecessary pieces people normally toss in.
Pack the right fabrics
Fabrics can make or break a winter carry-on. Materials like wool and merino stay warm even when damp. Technical synthetics wick moisture and trap heat without bulk. Cashmere is one of my favorites because it gives real warmth in a thin, packable layer.
In the winter, avoid cotton! It absorbs moisture, hangs onto it and leaves you feeling chilled. Once that happens, you end up adding extra layers to compensate.
Picking the right fabrics that work means you can pack fewer pieces overall.
The right way to compress winter layers
Compression can be helpful, but it is not magic. It saves space, yes, but it also adds weight because compressed layers become dense. That usually is not a problem with carry-on luggage, since most airlines do not weigh it, but you will feel it when lifting your bag into the overhead bin or walking long distances through airports.
I compress only what benefits from it. Puffer vests, fleeces and insulated mid layers bounce back into shape easily. Sweaters, especially wool and cashmere, get folded normally so they keep their structure. Selective compression gives me the space I need without turning my suitcase into brick weight.
The one thing that saves a winter carry-on every time
A foldable tote is the item that rescues me on every winter trip. It weighs almost nothing, but it solves every unexpected moment. I use it when I peel off layers indoors, when I pick up snacks or small groceries, and when I want easy access to gloves and hats without opening my main bag. It is also helpful if I end up buying souvenirs and need extra luggage. This is when I’ll just check the roller carry-on bag.
My favorite is the Paravel foldable tote because it is durable and packs flat. I keep it in the side pocket of my carry-on.
What your winter carry-on should feel like
When everything is packed, the bag should feel organized and manageable, not stuffed. Even though winter gear is bulkier, you can travel with a carry-on when the pieces work together and your layers do more with less.
The goal is simple: warm, versatile outfits that let you move from a cozy café to a snowy street without needing a full wardrobe change.
But, friends, this definitely will not work for ski trips! There’s just too much snowsport gear and apres-ski outfits. You’ll probably have to check a bag for that.