How to Pack a Carry-On for Winter Travel

For those of you traveling to the northern tundra of the U.S. who currently live in the balmy south or just traveling from frigid coast to frigid coast, packing for winter can be a pain. Coats, boots, and scarves are all bulky and with airlines charging crazy fees for baggage (including some now charging for carry-ons *cough United, Frontier cough*). How do you organize your carry-on bag and not feel like you have to leave behind all of the clothes that will keep you warm? Glad you asked!

If You Have Presents, Ship Ahead

Now if you’re reading this post-holidays skip down to Consolidate Your Clothes. Otherwise, your carry-on is no place for all of those Christmas/Hannakuh presents you are bringing home for the holidays. When I lived further from my family I shipped everything to either my parents’ or my brother’s house usually as I ordered it online. It was just way easier and since I do almost all of my shopping online now, it just made sense. If you’re worried about wrapping those gifts, you can easily swing by Target or a drugstore to pick up gift bags and gift wrap when you arrive.


Source: Hard Graft


Consolidate Your Clothes

A good rule of thumb anytime you travel is to layer, but don’t go crazy! Sweaters can take up a huge amount of space so bringing more than two is a bad idea (it’s either the sweaters or the shoes…your choice). And when I say bring, I mean you wear one and pack one. To give you an idea of what you should bring for, say, a five-day visit, I’ve outlined my suggestions:

Pack – 1 sweater, 1 pair of pants, 4 shirts, 1 dress or dress outfit (for the holiday dinner or for the night out), 4 undies, 1 bra (for the ladies – ha!), 4 pairs of socks, 1 pair of dress shoes (maybe 1 additional pair if they fit), 1 set of PJs, 1 pair of knit gloves, 1 knit hat, decanted toiletries and makeup (if short on space see my morning gym bag and purse makeup bag suggestions).

Wear – 1 sweater, 1 pair of comfy pants, 1 shirt, 1 pair of boots, 1 scarf, and 1 coat (plus socks and underwear and the like).

Pack Your Clothes

Once you’ve decided what to pack and laid it out so you can see what you have, it’s time to pack with purpose. Grab your carry-on and pack in the following order, rolling all clothes as you go:

  1. Shoes on the bottom with socks tucked into shoes
  2. Sweater
  3. Pants
  4. Dress (or dress outfit)
  5. PJs
  6. Shirts
  7. Undies rolled and tucked into bra
  8. Knit gloves tucked into knit hat
  9. Toiletries and Makeup (in clear plastic bags if necessary and should be easily accessible when going through security).

This should leave you plenty of space but before you start squeezing in extra clothes, don’t! If you are going home for the holidays or going on vacation, there is a very high likelihood you will be bringing stuff back with you.

What You Are Wearing12-17-16-carry-on-coat-scarf

If you haven’t figured out by now, the items you’ve left out to wear to the airport are the heaviest and bulkiest. Wear the most comfortable boots you can get away with. I would also wear a cozy cardigan so if for some reason I do get hot, it’s easy to take off while sitting in an airplane seat. Basically, you should be wearing something similar to hers, but you are allowed to have a more frazzled look on your face. Holiday travel is stressful, ya’ll!

Working double duty on airplanes are the following:

Scarf – Take the biggest scarf you have. I have a blanket scarf that I take on planes so when it’s not wrapped around my neck, it can be over my lap.

Coat – Your winter coat is bulky and there are times that I’ve shoved it in the big front pocket of my carry-on or laid it on the top of the suitcase in the overhead bin. However, I always end up wishing I had it to act as a pillow.  If you do this, just turn it inside out so you don’t get the outside dirty. As a bonus you don’t have to lug around your travel pillow!

The Personal Item

I think all airlines let you bring a personal item for free (read purse, backpack, or messenger bag). As somebody who has traveled a lot, I would encourage you not to go crazy here! I will do my suggestions for the perfect personal item carry-on soon, but basically this should easily fit under the seat with room to squeeze a foot or two in if you need to stretch your legs. Pre-load your phone with what you need (books, games, music) and use that primarily. Your seat mate will thank you for not constantly wiggling around to get something out of your bag. For winter, do bring a travel lotion and lip balm with you because you will get dehydrated, especially on the plane.  Also, suck water down like it’s going out of style.


The basic gist is this – You don’t need to bring a ton of clothes when it’s cold out. Yes, you need your warm boots, coat, etc. But if you can’t fit that brocade puffy skirt into your carry-on, you likely won’t miss it when you’re nice and cozy in your pants and boots! By just doubling up on wears for the bulkier items like pants and sweaters you can save yourself a bunch of room and baggage fees.


Still sitting on top of that suitcase to make it close?  Ask me a question about how to consolidate your mess!