Let me start by saying—I should have known better.
I’ve been to Washington, D.C. before. I know how the weather can be. And yet, for some reason, I let myself believe that since the cherry blossoms begin to bloom in March, it couldn’t be that cold.
And knowing that NYC is further north should have been enough of a warning. But, as a Louisiana girl who thinks March means sandals and sundresses, I was completely out of my depth. Where I’m from, March is when you start showing off those fresh pedicures, not layering up like it’s winter all over again.
After checking the New York forecast for the hundredth time, I had to accept reality—my usual springtime wardrobe wasn’t going to cut it. So, I did what any over thinker would do… I started shopping.
Shopping for the Trip: The Mission to Stay Warm & Cut
Now, let’s get one thing straight—I am not a shopper. But this trip required effort. I needed clothes for both me and my daughter, and since we wear the same size, I took the easy way out and just bought two of everything. (Also, I wanted us to match for safety reasons. She wasn’t thrilled about it at first, but by Day 2, she was all in.)
The Essentials: What I Bought
✔ A warm but lightweight coat – Not too bulky, but warm enough to handle the DC breeze and those NYC winds. Green for me. Gray for my daughter.
✔ Gloves & a satin-lined beanie – Because protecting the hair is just as important as staying warm.
✔ Joggers, sweatshirts & thermals – I saw a blogger wearing the cutest yellow jogger set from Target, and I knew my daughter and I needed it. From there, I stocked up on comfy, stylish jogger sets that weren’t too thick (since I was layering with thermals).
✔ Luggage & packing cubes – Fun fact: Neither of us owned a proper suitcase. The ones we did have were all in my college-aged son’s possession. I bought an iFly carry-on suitcase. I also got a LuggageX suitcase for my daughter. Finally, I purchased some luggage cubes (which turned out to be life-saving for space).
✔ A secure travel backpack – I’ve seen way too many movies. I’ve watched TV shows about tourists getting their stuff stolen in NYC. I wanted a backpack that was not easy to break into, and this one checked all the boxes. It is an Anti-Theft Backpack with hidden zippers of the main pocket and a secret pocket at the back. It held our lotion, small umbrella, and hand wipes. When we didn’t need our gloves or beanies, we threw them in there.
Unboxing & Packing: The Moment It All Felt Real
Even though I’m not big on shopping, I won’t lie—when all those boxes started arriving, it felt like Christmas morning.
I laid everything out to make sure it all worked, and then got to the part I actually enjoyed—packing.
Since I refused to check a bag, everything needed to fit in our one carry-on. That’s where the luggage cubes saved the day. If you haven’t used packing cubes before, trust me, they are a game changer. They kept everything organized, and I had more space than I expected.
Once everything was neatly packed away, I had a proud mom moment. I had planned, shopped, packed, and managed to keep us stylish, warm, and prepared.
What I Wore in Washington, D.C. & New York City
Here’s how our outfits held up in real life:
Day 1: Washington, D.C. – Exploring & Walking
Since it was a school trip and it was the first day of the trip, everyone wore the same neon green pullover. My daughter and I paired it with some jeans, comfortable shoes, our beanie, and coat.
Day 2: Washington, D.C. – Mount Vernon, The White House & More
✔ Joggers, sweatshirt
✔ Thermal top under a sweatshirt
✔ Sneakers (again, all the walking!)
✔ Gloves & beanie (definitely needed them by the water!)
Day 3: Washington D.C then New York City
✔ The yellow jogger set (because we needed a cute, comfy outfit for all the shopping!)
✔ Sneakers
✔ Crossbody bag (for easy access to my wallet while shopping); Travel backpack
Day 4: Walking the Brooklyn Bridge & Wall Street
This was our no matching day. My daughter decided to wear her neon pullover again since we were going to be so deep in the city and going on a boat ride. I decided to wear jeans and a light pullover with my coat. We both decided to wear our beanie and gloves. We knew it would be cold on the water and it was raining.
Packing & Shopping Tips for D.C. & NYC in Late Winter
1. Don’t assume it’s warm just because the cherry blossoms are blooming.
The flowers may be out, but so is the cold air.
2. Start shopping early.
If you need winter clothes, grab them in February while they’re still available.
3. Pack smart with luggage cubes.
They save so much space and keep everything organized.
4. Wear comfortable shoes.
Between D.C. and NYC, expect to walk a lot. Sneakers or supportive boots are a must.
5. Bring a secure backpack.
Pickpockets love tourists. Get a theft-proof backpack with hidden zippers.
6. Layer up.
Stick to thermals, joggers, and light but warm jackets instead of one bulky coat.
Final Thoughts: I’d Pack the Same Way Again!
Looking back, I feel like I nailed the packing. Our outfits were warm, comfortable, and perfect for both cities. And thanks to those packing cubes, everything fit in one carry-on.
Would I change anything? Maybe pack an extra layering top or two, but other than that—I’d do it all over again the same way.
So, if you’re heading to D.C. or NYC in late winter, remember: layer up, pack smart, and don’t overthink it.
What’s Your Go-To Travel Outfit?
Have you ever completely misjudged the weather on a trip? Or do you have a foolproof travel outfit strategy? Let me know in the comments—I need all the tips for my next adventure!
