winter packing: what to bring

Packing in a carry on is tough enough, but add winter coats, sweaters, and boots to the mix and you’ve got a real challenge on your hands.

So … I’m going to try it! I’m packing for a 5 day winter trip using only a carry on.

Sounds difficult as it is, but to make (packing) matters worse, this trip has an itinerary that calls for clothes all over the map:

  • A hike (that calls for real athletic shoes, not cute ones)
  • Sightseeing in the city, in the cold (with slushy streets, so weather boots are a must)
  • Hot tub time (that requires a swimsuit and flip flops)
  • A night at the theatre (that calls for dressy clothes)

So, my challenge?

Pack athletic clothes, weather clothes, fancy clothes, swimwear, and regular clothes (like PJs and travel clothes) all in one carry-on suitcase.


But let’s do it! 🙂

In this post, we’ll cover:

  • Start Here: Download The Packing Planner
  • Step By Step: How To Decide What To Bring
  • My Packing List
  • Packing in a carry on: Is it worth it?


The key to successful carry on packing? Planning.

Because this is such an important step for me, I created a free, downloadable packing planner for you! You can download the packing planner right here and here’s an example to get you started. These few minutes of planning make the packing process go faster and feel effortless.

Before you start to pack, go ahead and fill out the weather and activities sections of your planner. (You’ll fill out the outfits section later, as you’re going through the step-by-step part below.)

Tip: I’ve found it’s best to write in pencil, so you can adjust as you go along.


Create a space where you can gather everything, like your bed or a clothing rack. Have your packing planner close by for reference.

STEP 1: Start by gathering the clothes you’ll need for any specific activities + special events.

For example, if you’re going on a hike (like me), gather your hiking clothes, shoes, and jacket. If you’re dressing up for a fancy evening or heading to a wedding, gather your outfit, shoes, and any accessories including a clutch, jacket, or shawl.

These necessary things can add up quickly, so it’s best to gather them first and then “fill in the blanks” with your other clothes.

STEP 2: Gather PJs, underthings, and toiletries.

PJs and underthings are straightforward enough, but toiletries can be tough. So I get travel sized items, and split them into smaller bags — that way, they are flexible and can easily fit into nooks and crannies of my suitcase.

(And … don’t forget to separate your liquids for security.)

STEP 3: Gather regular clothes.

Now, it’s time to “fill in the blanks” with regular clothes.

  • First, ditch the oversized boyfriend sweaters and pack two lightweight sweaters instead. Lightweight can still be warm — look for merino wool or cashmere. If you’re lamenting the loss of your oversized sweaters, I know, it’s a bummer. Oversized boyfriend sweaters are a signature element of my style, so it’s hard to let them go. But they took up too much real estate in my carry on for this particular trip, so they’re out.
  • Then, add two or three long sleeve shirts — one plain tee and one cute layer, like a striped turtleneck. You can wear them underneath your sweaters for extra warmth or wear them on their own.
  • Finally, add two bottoms (one casual, one dressy) and add a dress, if desired.

Travel is the time to go with what you know works. For me, that means I went with a neutral color palette. It doesn’t look that interesting on paper, but in real life, I feel happy and put-together in these neutrals — plus when I add that rich cognac coat on top, it jazzes things up in the best way.

STEP 4: Gather shoes.

You’ve probably already gathered your athletic shoes and dressy shoes in Step One. Now, fill in the blanks with any other shoes you need, making sure to reference your packing planner to guide you.

I’ve got four pairs of shoes listed for this trip — yes, four. Not exactly the “minimalist” way, I know. Usually, I wouldn’t recommend bringing this many shoes, but sometimes, you can’t get around it — you need your non-cute running shoes and a pair of nice heels and weather boots.

Four pairs of shoes may not be ideal, but I wanted to show you that it’s possible — even when traveling in a carry on.

STEP 5: Edit

Grab your packing planner and start assigning outfits to each day and each activity. This should help you find pieces you can edit out easily.

See if any items can pull double duty:  i.e. Could your daily base layer double as a hiking top? Could your PJ top double as a day out top in a pinch?

And don’t be afraid to wear things twice — a base layer will help keep your sweaters fresh, so you can get multiple wears out of them. You can also get more wears out of your clothes if you bring a sanitizing travel steamer or wash your clothes in the sink.


There’s one thing you should know about this packing list before we jump in:

I only used pieces I already had in my closet. So, this isn’t necessarily an ideal packing list — but it is a real packing list. Of course, it would be better if I had a compressible, waterproof jacket, or one pair of shoes that could serve as hiking shoes and weather boots. But, I don’t have those things, and I wanted to see if I could make it work without buying anything.

The good news? It worked!

Let’s take a look:


1 | BASE LAYER TEE | Great for adding warmth under a sweater, and it also doubles as a hiking top.


3 | WHITE SWEATER (OLD) | SIMILAR IN CASHMERE (UNDER $70) | My black and white sweaters are exactly the same, but they are chic, easy to wear, and lightweight (AKA easily packable).


5 | WINTER COAT BY ARITZIA | SIMILAR | SIMILAR ($150) | Yes! I found my winter coat! And I feel great about it because my blogging bestie, Lee, happens to have the same coat — she’s Canadian so she knows her coats. Wondering how I’m going to fit this in my suitcase? I’m actually going to bring it on the plane with me instead.

6 | FLEECE | This jacket is for the hike. I really should have a warmer, weather resistant jacket, but I don’t. However, if you’re in the market, here’s one that’s thigh-length with a hood, and here’s a shorter version. Both are compressible and packable — meaning they pack down into a tiny bag. Amazing!

7 | BEANIE (MADE IN USA) | This guy adds a pop of color to any outfit and mirrors the color of my coat and purse — you know, if I ever want to “bookend” my outfit with the same color. Which I definitely do.


9 | COATED LEGGINGS (OLD) | SIMILAR | SIMILAR (FLEECE LINED) | SIMILAR (FOR LESS) | These will pair well with my turtleneck dress and ankle booties for a dressed up look.

10 | YOGA LEGGINGS (MADE RESPONSIBLY) | Great for the hike, travel days, or lounging.



13 | WEATHER BOOTS (ON SALE)| SIMILAR (MADE IN USA) | These fleece lined boots will keep my feet warm and dry when we’re out sightseeing and walking around slushy streets. I don’t have a sleek pair of waterproof boots (like these waterproof chelsea boots) but if I did, I’d bring them instead for the versatility.

14 | ANKLE BOOTIES (MADE RESPONSIBLY) | SIMILAR (FOR LESS) | My dressy shoes for the trip — they’ll work with just about anything, but I plan to wear them with my turtleneck dress, coated leggings, and coat on nights out.

15 | ATHLETIC SHOES | Sometimes you just need your non-cute running shoes. However, if you can get away with cute sneakers, this bootie-inspired pair would be my pick.


(Not shown)

17 | AWAY CARRY ON SUITCASE | I’m done with soft-shell suitcases — the hard shell is where it’s at. I’ve had my AWAY bag for about 6 months now, and I’m a solid fan. My favorite thing? It’s ridiculously lightweight — in fact when I first got it, I was unimpressed with how flimsy it felt. But it turns out, the bag is indestructible. However, something to note: it doesn’t expand. I actually like that about it now, but it took me a little while to get used to.

18 | SMALL CROSSBODY BAG | For dressier nights.

19 | TRAVEL TOTE | My travel tote is technically a camera bag, which means it’s a little bulky and heavy on it’s own. So, instead I’d recommend this travel tote. It hits everything on my checklist: it’s beautiful, it’s got a zip top to keep everything secure, it’s got lots of pockets (including pockets on the outside), and it’s made responsibly.



Here’s the thing. Packing for this trip was capital C challenging. Maybe you’re a winter packing pro, but I am definitely not. I mean, I managed to pull it off. But I kept feeling like I needed to buy certain items specifically so I could fit them in a carry on. (Compressible, packable coat! Waterproof boots that are also cute and dressy! Thin sweaters, ideally cashmere or wool!)

Of course, it’s ideal when you can pack items that pull double duty, but sometimes, it’s not practical to buy new pieces just so they fit into your suitcase.

So here’s my mantra with this whole thing:

Hold lightly.

Hold lightly to the idea of packing in a carry on.

If you can’t make it work, let go and just pack in a bigger suitcase. No big deal. The ability to pack in a carry on isn’t the end all be all.

Hold lightly.

• • •

There you have it! Whew, thanks for sticking with me! The posts after this will be shorter, I promise.

And on that note, this is part one of a four part series — we’ll be looking at this packing list all week! Here’s what’s coming up:

  • Tomorrow: I’ll show you how I fit everything into my carry on (in my first-ever video, yikes!)
  • Thursday: I’ll show you how I combine these pieces to make outfits for each day and activity.
  • Friday: I’ll share what’s in my airplane tote.

It’s going to be a fun week! See you tomorrow!


Like it? Share with your friends!

, 0 points
What's Your Reaction?
Angry Angry
Cute Cute
Fail Fail
Geeky Geeky
Lol Lol
Love Love
Win Win

Leave a Reply

Your email address will not be published. Required fields are marked *

winter packing: what to bring

log in

reset password

Back to
log in
Choose A Format