Traveling with less is not as easy in the winter, bearing in mind the size of some of the clothes involved,  but it can be done.  Having spent the past hour tussling gently with what seems like a particularly recalcitrant octopus rightly full of its own opinions, this is what I’ve learned about packing for a winter week in a carry on.  Welcome to the Packing Light Winter Edition.  I’m using my winter packing list for Europe, but there are plenty of trips for travel to other destinations too.

Not quite ready to pack yet?  Why not pin this for later!

Packing Light Winter Edition: What do you really need?

This applies just as much, if not more, to winter packing than summer packing.  If you’ve read my travel hacks before, you’ll know that I am insistent on packing for the trip you are really going to have, not the one you think you might.  While in summer I might happily abandon all kinds of extras, the same behaviour in winter has left me shivering and shopping.  So bear that in mind.

If you are headed somewhere very wintery, then you might elect to buy some essentials there.  This thin-blooded Brit only realised the full meaning of windchill when faced with a snowy Chicago February out at Oak Brook.  There, the wind hit like a knife.  I’d bought the snow boots I planned to buy on that trip.   I ended up buying a new winter coat too, from a city that knows how to handle the chill.

Packing Light Winter Edition: Thinking it through before you pack

Be real. Pack for your life as it is.  In winter, for me, that means accepting that I am not very good in the cold.  I creak and I hurt if I get too chilly.  So priorities for me have to be the extras that make outside bearable in the temperatures I’ll be experiencing.  My trade off is more gear that I can wear wandering around in the chill, and less gear suitable for going somewhere posh.

As always, check out your destination weather and temperature up front.  How is that going to feel to you?  And in winter, learn from my mistake and think about wind chill too.

Then where’s your destination?  Will you be in the city, and if so, can you expect clear paths if it snows?  Or will you be outdoors in wild places, where you’ll need to be water resistant if not waterproof from head to toe.

How To Pack Winter Clothes Into Luggage: Choose Your Travel Outfit First

If you’re wondering how to pack winter clothes in your luggage, I have a tip for you.  In winter, I always sort out my travel outfit first, as it’s a good opportunity to get the most bulky items out of your case and on your body.  It helps if you can achieve that without getting into the “wear everything you have” ultra low cost airline scenario.  Overheating makes me as grumpy as being chilly does, although you may have more fortitude.

Packing Light Winter Edition: What I wear

My winter uniform is pretty much this:  knee boots or walking boots depending on destination, leggings or ponte trousers, a jersey soft cami, a long top and my biggest jumper.   If time at the airport stresses you, make sure your long top is one you’re happy wearing on its own, should you need to shed the jumper.  On top of this goes my big puffy jacket, a scarf, hat and gloves.

I find it helpful to have a jacket with massive pockets.  This means that when you go through security, you can stuff your scarf, hat and gloves in the pockets, leaving you less individual pieces to wrangle when you’re settling everything into trays.

Packing Light Winter Edition: A word on Comfort

Make sure that everything you set aside for your travel outfit is soft, gentle on your body and easy to wear.  Nothing that rides up, digs in, or has you checking for a reflective surface to make sure it’s still ok.  Being self-conscious or uncomfortable is never a good contributor to a trip.

How To Pack Light For Winter Travel

I’d say that I chose my colours for a week away, but in practice my winter wardrobe is actually twenty shades of black with a few small contrasts.  If yours is more vibrant, then you probably already have a few themes, of which you can pick one.

Then it’s maths time.  If you’re wearing tops and bottoms, then you need two or three tops to each bottom.   If I can fit them in, I’ll take enough tops for at least three days to avoid the hassle of trying to wash and dry them quickly.  Plus you’re traveling to enjoy the experience, not to test out the laundry facilities of the world.  I’m wearing one big jumper on the way out, and will pack another, plus a thinner layering piece.  Everything in my bag will go with everything else.

Packing Light Winter Edition: Surprise Choices

Don’t write off dresses for a winter trip.  I find that with a cami and leggings underneath, they’re actually warmer than a top.  And if you choose the right dresses, they can fold down into very much the same space as a long top.

As far as shoes go, winter makes for more challenging packing in a carry on.  I wear knee boots, and take ankle boots.  The ankle boots get thoroughly stuffed with everything I can possibly fit in them for the journey.  It might be possible to stick with one pair of boots for a trip, but where I am walking loads, that can make for sore feet.  And with two pairs you get the chance to let the first dry out in wet or snowy weather.

How To Pack Sweaters In A Carry On: Compression is your friend

For a winter trip, compression is pretty much the answer to a week in a carry on.  First up, I use my packed pair of boots as their own compression device.  They fit my undies, socks, spare gloves and scarf, and on the way home anything fragile I’ve acquired.

Packing cubes may add weight, but usually my personal packing struggle is more about space than weight.  For this reason, I tend to opt for smaller – and lightweight – packing cubes, compressing everything down nicely and making case Tetris easier to achieve.  I use my spare jumper to fill the space round my boots (which are in a bag), then the cubes are fitted around.   I have some very flat packing cubes, which are particularly good at slotting together within a carry on space.

Packing Light Winter Edition: Toiletries

As far as toiletries go, you may have a preferred selection already.   Over the years, I’ve got much better at estimating how much I am going to need for a week, even counting out the number of pumps of cleanser to go in the pot.  For winter, make sure not to forget lip balm, and a more intense moisturiser and hand cream.  Heavy weather can make you sore if you don’t look after your skin.

If you know there will be toiletries at your destination you can use, then pack lighter.  I’ve got a skin condition that makes me react badly to some brands, so I tend to bring my own.

Packing Light Winter Edition: Entertainment And Working on the Road

For a week, I always make sure I have room for a tablet/Kindle and a book in case of delays.  I’ll also have my travel journal and a couple of pens.  When I am working on the road, I’ll have my laptop with me.  I’ve changed from a widescreen to a smaller version to make that easier.

All of these will normally fit in my personal item, along with my essentials.  Don’t forget your memory device of choice, all the necessary cables, and your travel adaptor.  I keep mine in a clear bag (a pencil case, and much cheaper than a specially designed bag), so there’s less chance of my returning without a crucial piece of kit.  Those plastic coiled hair ties are great for keeping the cables tightly wound together, avoiding a mass exit of wires every time you open the bag.

Packing Light Winter Edition: Essentials

I keep a checklist of my absolute essentials for any trip.  That includes

• wallet
• passport where needed
• keys (unless you have someone to let you in on your return)
• prescription meds, and a few basic extras in case of need
• glasses or contacts
• phone and charger
• adaptor if required and tech charger
• destination details, plus any hard copy tickets and reservations
• details of your travel insurance

Packing Light Winter Edition: my next trip

I’ll be off for a week next month.  Here’s my packing list for that trip.  We’ll be walking rather than hiking, wandering around towns and villages.  We’re staying in an airbnb, so I can rely on washing some things if needed.

Packing Light Winter Edition: Practice Pack

I’ve done a practice pack – highly recommended if you have time – and that all fits into a hard shell carry on case plus personal item.  I haven’t got as much space as I would have in summer to bring back any extras, but in truth, the more often I travel, the less I acquire on the way.  What I know I’ll want to bring back on this trip will fit into my personal item (probably a small backpack).

I’ve had to work hard to get all this in my smallest hard shell, but it does fit.  The secret for me is in absolutely stuffing my boots, and in using the space between the handle ribs to roll smaller items like camis and tops.  Both of the dresses I am taking fold down to nothing, and take less room than some of my tops.  But as they are both just above knee length, they’ll keep my legs warmer than a top.

Want More Travel Hacks?

You can check out the summer edition of this carry on post here.  We’ve also talked about packing for a road trip,  or a business trip.  For more thoughts on life on the road, I put together 50 Travel Hacks from 50 Years On The Road: a summary of 50 years of adventuring and what it has taught me.

Author: Bernie