How to Pack: Long Winter Weekend in NYC

I’m going to talk about how to pack for a long winter weekend in New York City! My husband surprised me with a trip to NYC for New Years 2023! This was a dream come true for me, as I have always wanted to go to New York, and going at the holidays is especially fun. In this post, I will show you my process of packing for a long weekend using only a carry-on suitcase and a personal item.

Being from Texas, I am very unused to Northern weather. I did a lot of research before we left for our trip, and found that the weather was going to be fairly chilly, but supposedly not snowy. This will effect what kinds of clothes you can pack, and how much, as winter clothes are much more bulky than summer. I knew it would be rainy one day, so I accounted for that in my packing plans as well.

We were going to fly in on Friday afternoon, spend Saturday and Sunday in the city, and then fly out on Monday afternoon. So, we had two full days and two half days to pack for. As I had never been to NYC, I knew that I was going to want to do a lot of sightseeing. I kept this in mind as I started my packing.

Disclosure: Some of the links below are affiliate links. This means that, at zero cost to you, I will earn an affiliate commission if you click through the link and finalize a purchase. 🥰

Suitcases / Backpacks / Packing Cubes

I have used the same carry-on suitcase for years now, and it has held up amazingly. I use the Swiss Gear Wenger Softside Luggage with Spinner Wheels in the carry-on size. It went with me on a two week trip all through England and Paris. It was gone with me on domestic flights to North Carolina and Colorado. I have been using this bag since 2017 and it is still in great condition. I highly recommend this suitcase if you enjoy using a soft sided suitcase.

Swiss Gear Wenger Softside Luggage with Spinner Wheels

For my personal item, I highly recommend the brand PacSafe. They make cute backpacks that have lots of anti-theft features that are perfect for travel. It has locking zippers, a detachable strap that you can wrap around a table leg, RFID blocking pockets, and anti-slash light weight steel mesh hidden underneath the fabric. My particular model is no longer available (but it has served me well for our England trip, our China trip, and several domestic trips), so I have included a comparable model that is available now.

PacSafe Women’s Anti-Theft Backpack

I also swear by my crossbody Travelon Anti-Theft Travel Purse! It has locking zippers, RFID blocking credit card slots, an anti-slash crossbody strap and way more room than it looks like it has! I love purple, as you have probably guessed, so I enjoy that it is in a fun color as well. I don’t think they have my particular model anymore, but I have included one that is very similar.

Travelon Anti-Theft Boho Slim Bag

I have used the eBags Packing Cubes for years! These have been such a huge game changer in how much I am able to pack, as well as how organized I can stay while traveling. These come in a multi-pack of various sizes, and in many different colors.

eBags Classic 6 Piece Packing Cube Set

Getting Started Packing

I have a few little extras that I swear by to help make my packing experience easier. One of them is using a jewelry roll. This is a great way to bring jewelry with you and keep it from getting tangled or lost. I have used this one for years and years. I honestly don’t even remember where I got it. (Also, I just recently got a new one – I’ll be posting about it soon!) I have included something that is comparable.

Travel Jewelry Organizer Roll Bag

I also like to bring a laundry bag with me on my trips. This is a way to keep your dirty clothes separated while you are traveling so you don’t get your clean clothes dirty by keeping them in the same space in your bag with the dirty ones (I feel like that is pretty self-explanatory, but just in case it’s not…)

Re-packing Tip: On our way back home, we actually put all of our dirty clothes back in the packing cubes, and put all clothes that we didn’t end up wearing in a separate cube. This is a good way to save room and still keep the clean and dirty clothes separate!

Travel Size Laundry Bag

I also really like to bring an extra collapsable tote bag with me when I travel. This one is super compact and lightweight. It is a good idea to bring an extra bag with you if you are doing carry-on only travel so you have some extra room if you buy a lot of souvenirs. We actually ended up using this as a personal item on our way home from NYC to hold souvenirs. Bonus, this one zips closed and has extra pockets!

Collapsable Tote Bag

I also use a shoe bag to keep my shoes from getting anything else in my suitcase dirty. You can easily use a plastic grocery sack for this if you don’t have a dedicated shoe bag. But, I enjoy having a dedicated bag (plus it’s just cute!)

Travel Shoe Bag

Packing Tip: Always put your bulkiest items in the bottom of your suitcase. For me, this was my nice boots. That way they are at the bottom and won’t crush anything else in your bag.

Clothes for a Long Winter Weekend

I always make a packing list when I start packing. This way I know that I won’t forget anything. It is also a good way to keep yourself from overpacking. For this trip we were going to be spending two full days and two half days in NYC. Most of that time was going to be spent outside sightseeing. However, we were also going to see a Broadway show, and we had reservations at a nice restaurant for New Years Eve, so I knew I would need at least one nice outfit.

The clothes I decided to bring:

  • 2 Pairs of Jeans
  • 3 Shirts
  • 1 Dress
  • 1 pair of PJs
  • 1 robe
  • 1 fancy cardigan
  • 2 pairs of boots – one fancy, one casual
  • Undergarments (including tights)
  • Outerwear
  • Thermals

As you can see, I went fairly minimal. I decided I would rewear my fancy outfit as I wouldn’t be wearing it for very long on either occasion. I also am a firm believer in rewearing jeans. You can get multiple wears out of one pair easily. I also only brought three shirts because I figured I would rewear my travel day shirt on our return flight (or that I might buy something while I was in NYC, which is what I ended up doing!)

The first outfit was my travel outfit. I wore my bulkiest shoes on the plane, which happened to be my casual boots that I would be wearing for most of the trip. These jeans are pretty stretchy and roomy, so I knew that they would be comfortable for the plane. (I will do another post soon about airplane travel tips.)

The second outfit reused the jeans and boots from my travel day. The third outfit used my one other pair of jeans and my final shirt that I packed. I also wore this with my casual boots. So, the only things I packed were the plaid shirt, pink shirt, and gray jeans. Everything else I wore on the plane.

This was the nice dress and cardigan that I packed for our two fancy occasions. I went out to dinner on New Years Eve in this outfit. The next day I went to see Phantom of the Opera on Broadway in this as well. I wore it with thermal tights and my fancy boots from earlier in this post.

I packed one set of PJs, since we were only going to be there for three nights. I didn’t feel like I needed more than that. These two pieces also roll up quite small, which is ideal for packing carry-on only. I also brought a robe with me so I could have a cozy layer in the hotel.

The last picture contains my thermal tights, which I wore with my fancy dress. I will say that these were fantastic! My legs were perfectly cozy in them, and we ended up walking quite a long way in the cold evening while I was wearing these. I will include a link for these here.

Women’s Opaque Fleece Lined Tights

I brought thermals, which I actually didn’t end up wearing. This is my one thing that I brought that I now regret. I didn’t know how cold it would feel in NYC with all of the wind. I had heard that the wind makes it feel much colder than it is, but I ended up feeling fine with just my outerwear.

Speaking of outerwear, I want to sing the praises of this coat! I saw a flight attendant YouTuber that I follow recommend this coat and I love it!! (Kat Nesbitt – go check out her videos!) It is super lightweight and rolls up really compact. I was actually able to stuff it into my personal item at one point when I was hot in the airport. It is also water resistant. I was able to use it to keep dry when it was rainy in NYC! I will give you the link to it below! Also, these gloves were great! They were super warm, and you are still able to use a smartphone with them on!

Amazon Essentials Women’s Lightweight Water-Resistant Hooded Puffer Coat

rivmount Winter Gloves Men Women,Waterproof Touch Screen Gloves

I don’t know if you can tell, but I still have a bunch of room in the top of my suitcase after putting in all of my packing cubes. In the suitcase is two shirts, one pair of jeans, one dress, one cardigan, one robe, one set of pjs, undergarments (including socks and tights) and thermals, and my fancy pair of boots. Everything else I would be wearing on the plane.

Packing Your Toiletries

I have used the same toiletry bag for years, because it is fantastic! The eBags Pack-It-Flat Toiletry Kit is the best toiletry bag I’ve ever found. As the name suggests, it packs super flat, which gives you extra room in your carry-on. It has a hanging hook, so you can hang it from a towel rack in hotels that don’t have much counter space. I pack anything in here that is not a liquid. I will get to those next.

eBags Classic Pack-it-Flat Toiletry Kit

If you are flying, like we were, you will need to make sure you follow the 3-1-1 rule for TSA. Each liquid must be 3.4 oz or smaller, in one clear quart-size plastic bag, and only one bag per passenger. I decided for this trip to use the shampoo/conditioner/body wash/lotion that the hotel provides. If they didn’t have one of those items, I knew it would be simple to go and purchase it at a drug store somewhere in the city. All of the liquids I brought were things that I use everyday that I thought might be difficult to find at a moment’s notice. I generally just use a quart-size Ziplock bag for my liquids.

Packing Tip: Liquid makeup, like foundation, concealer, and mascara, is considered a liquid per TSA guidelines. These have to go in your liquids bag. (I’ve seen a bunch of YouTubers and bloggers neglect this and it always bothers me!)

I always pack my liquids bag in the front pocket of my carry-on suitcase. This way it is in an easy to access spot. Once I’m through security I put it in my toiletry bag inside my suitcase for safety (and so it won’t get compressed in the overhead bin).

I pack my makeup separately from my toiletries. I just find it easier to do this, but you could absolutely put all of that in your toiletries bag if you prefer. Again, this is only my makeup that is not considered a liquid. This bag is a free with purchase bag that I got once from Clinique.

Once I put the toiletry bag and makeup bag in my suitcase, then I am fully packed in my carry-on! I still have room, which I did on purpose so I would have room for the inevitable souvenirs that I knew I would be bringing home.

What I Pack in My Personal Item

I have a few things that I tend to always pack in my personal item. One of these is my medicine. On the chance that your carry-on has to be gate checked, it is always a good idea to keep your medicine with you so that you don’t run the risk of being without your prescriptions. I got this little pill case on Amazon. It comes in a pack of three. Depending on where you are going, you might need to bring your prescriptions in the original bottle, but going to New York I didn’t need to worry about that.

MEACOLIA 3 Pack 8 Compartments Travel Pill Organizer Moisture Proof Small Pill Box

I also like to bring a zipper pouch with various first aid items. I bring bandaids, ibuprofen, antacids, Airborne, tissues, earplugs, and little toothpick/brush sticks. I love this little canvas zipper pouch, which I got on Etsy!

Airplane Mode Toiletry Bag

I tend to put my travel purse inside of my backpack. That way I only have one personal item, but I have a sneaky second item 😉 Here is a picture of all of the things that I tend to carry in my travel purse.

So here is what I brought with me in my personal item backpack! I stick my purse inside, and the zipper pouch. I also brought my Beats Headphones, my iPad, an eye mask, a hair clip, and my chargers.

Packing Tip: I always bring wet wipes with me in my personal item. If you are flying, always wipe down the tray table!! Those things are covered in bacteria and are not cleaned as often as you might think 🤢

Beats Solo3 Wireless On-Ear Headphones 

That is everything that I packed for my long winter weekend in New York City! If there are any items that you are curious about that I didn’t mention, please feel free to ask!

I will be doing a post soon about our trip and what we were able to do in two days in New York City! Be sure to check back for that one!

Do you have any packing tips that you swear by? Let’s chat down in the comments!

Love and happy traveling,


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