A weekend's worth of cozy outfits for a short NYC trip

I love, love, LOVE planning a packing list for a trip. Sometimes, it’s about showing out and showing off. I want to pack an outfit for every single activity, each one better than the first. Other times, it’s about utility. I need to conserve space, think about how much I’ll be walking, the temperature, and how many opportunities I’ll have to change. We try to carry-on all our luggage, especially if it's a short trip!

One rolling suitcase as my carry-on + one overnight bag as my "personal item"

When we went to New York right before Christmas, I knew it was going to be FREEZING and that we’d be walking a lot (roughly 12 miles per day, as it turned out!). I knew we’d be far away from the hotel for the majority of the time, and I couldn’t plan to change multiple times. Finally, I wanted to layer up; and I knew that since my heavy coat would be covering my outfits, I wouldn’t get many pictures of them.

With all of that in mind, I whittled down my outfit list to the following:

Pink sweater + black dress + thick black tights + combat boots to change into after we checked into the hotel.

Again, utility. I wanted to be cozy but also comfortable. This Ooey Gooey Sweatshirt (yes, that’s really the name) is from Popflex Active. This is truly the most comfy shirt I’ve ever worn. The material is like something from another planet, it’s so soft and buttery against your skin!

For the second full day, I packed a very boring combo of a hoodie and leggings. Once again, I wanted to be comfortable, because this was our BIG sightseeing day. I packed two pairs of leggings and two different colors of the same hoodie so I could mix and match.

The Cloud hoodie is another PopFlex staple in my wardrobe. It’s not quite as unbelievably soft as the Ooey Gooey Sweatshirt, but it’s a close second. It’s oversized in all the right places and it’s my all-time favorite hoodie.

Of course, I spent the entire day with my coat on, so the boring outfit didn’t matter too much. This coat is a faux-wool Time and True from Wal-Mart - yes, Wal-Mart, I’m cheap - but it has held up so well for me over the past few years. I stayed warm all day (well, except for my nose, which was exposed to the elements and nearly froze off my face).

That evening, we were going to see a show on Broadway, so I packed a strapless black dress that I had sewed for my graduation, and a gold long-sleeved top I got at TJ Maxx. I thought it would be a cute way to reuse the strapless dress in the winter, and I like the way it turned out! I left a trail of glitter EVERYWHERE I went.

While not my first choice for shoes, I ended up wearing a pair of over-the-knee suede boots. It added another layer of protection for my legs, which ended up still being a little cold; and my feet were crying out for mercy after walking a few miles in 5-inch heels.

The last day, I wore a black sweater and some cross-button jeans. I wore this all day. We walked around and did some more sightseeing before catching an evening flight back to Tennessee. I’d planned to change into my spare hoodie and leggings for the flight, but I ended up just wearing this the whole way home.

All in all, I only took one rolling carry-on and a black overnight bag, so we didn’t have to check any luggage. I also packed my laptop, some study materials, and a sewing project for the plane in addition to toiletries, socks, pajamas and makeup. I still had room to spare in my bags! I was pretty pleased. I definitely didn’t overpack and the clothes were perfect for the short trip - even if they weren’t the most Instagrammable.