Aaron and I got to go to New York City for Memorial Day weekend, and we spent a few lovely days soaking in the energy of the city. We did plenty of exploring, shop-hopping, and eating, but the real purpose of our trip was Broadway! We saw a musical a day — Dear Evan Hansen, Mean Girls, and (eep!) Hamilton.
A full travel video is coming your way soon (with our full itinerary and recommendations), but today we’re talking packing! I’ll share:
- How I decide what to pack
- A free printable packing planner for you
- The 20 items I brought
- The 6 outfits I wore on the trip, plus 12 bonus outfits!
Ready? Let’s jump in.
HOW I DECIDE WHAT TO PACK
The key to successful packing, in my opinion? You guessed it — planning. But it doesn’t have to be serious or complicated. I loosely follow these 4 steps and have fun with ’em:
1. Check the weather
The first two days of our trip were sunny, beautiful, and warm. Then the last two days were chilly, rainy, and dreary.
So I split my suitcase down the middle — half warm weather items, and half cold weather items.
2. Know your itinerary
Our itinerary included typical city things, but if there’s one thing I know about New York City, it’s that there will be lots of walking. Lots.
Years ago, on my first trip to NYC, I packed “the cute shoes” and ended up with sad, blistered feet for the rest of the trip.
Never again, I vowed. Never again.
So this time, I took a shoes-first approach to packing. Meaning, I picked out the most comfortable shoes I own and built my packing list + outfits around them.
The result? My feet were happy and blister free on the trip!
3. Stick to a color palette
I went with a black, white, grey, and caramel color palette — with a little interest via floral patterns and woven accessories.
Yes, all those neutrals can seem lackluster when they are just sitting in a suitcase. But, it doesn’t really matter how the clothes look in a suitcase — once those clothes are on, we bring life and vibrancy to them with our energy.
4. Try on each outfit and snap a photo of it
Once I arrive, I don’t want to spend time figuring out what to wear — I just want to throw on an outfit and get going! This step allows me to do just that.
MY PRINTABLE PACKING PLANNER
If you’re like me and you love a good printable, this one’s for you! You can download my packing planner right here and here’s an example to get you started.
Tip: I’ve found it’s best to write in pencil, so you can adjust as you go along.
THE 20 ITEMS I BROUGHT
All together, I brought:
- 3 pairs of shoes
- 3 tops
- 1 jacket
- 3 dresses/jumpsuits
- 3 bottoms
- 4 active/lounge items
- Plus a small purse, tote, and of course, my carry-on suitcase
Of course, for a long weekend, I didn’t even end up needing all of this — several pieces went completely unworn. This packing list is probably more appropriate for a two week trip. But while I could have pared down a bit more, it all fit in my carry-on anyway, so why not bring the lot? :)
Here’s the full lineup. If you see something you like, you can shop it and support Unfancy at the same time by using the affiliate links below.
New York photo by Katie L. Howell
1 / Woven Flats by Zara / similar by Frye
2 / Low Heels by Madewell (old) / similar by Madewell / similar by Everlane (made responsibly)
3 / Sneakers gifted by Nisolo (made responsibly)
4 / Sweater by HM
5 / Tank by Aritzia / similar by Urban Outfitters
6 / Crop top by Reformation (made responsibly)
7 / Jacket by Elizabeth Suzann (made responsibly, old) / similar by Aritzia (light weight for summer)
8 / Maxi Dress by Christy Dawn (made responsibly) *Not available online yet, search “Poppy Dress” to check availability / similar by Madewell / similar by Anthropologie
9 / Midi Dress by Christy Dawn (made responsibly) *Sold out, search “Lennon Dress” for the same dress in different fabrics / super similar by Reformation (made responsibly) / similar by Reformation (made responsibly) / similar by Anthropologie / similar by Sezane
10 / Jumpsuit gifted by Vetta (made responsibly)
11 / Mini Skirt by Everlane (made responsibly) / similar by HM
12 / Jeans by Citizens of Humanity
13 / Wide Leg Crops by Everlane (made responsibly)
14 / Yoga Leggings by Outdoor Voices
15 / Tank by Madewell
16 / Sweatshirt by Outdoor Voices
17 / Joggers by Outdoor Voices
18 / Crossbody Bag gifted by Lo&Sons *sold out in white / similar by Madewell in white
19 / Carry-On Suitcase gifted by Away
20 / Tote gifted by ABLE (made responsibly)
And finally, a few things that aren’t pictured: Toiletries. Hair Wand. Phone charger and tiny bluetooth speaker. Mahabis slippers. And a travel steamer.
WHAT I WORE EACH DAY
On the Plane: I like to travel as comfy as possible — no shame wearing joggers and a sweatshirt in the airport!
Friday Afternoon / Out and About: As soon as we landed and checked into our hotel, I changed into this dress that always makes me feel happy (here’s a similar dress). Pairing it with shock absorbing sneakers guaranteed I’d be comfortable for a full afternoon of walking.
Friday Night / Dinner and Broadway: Wearing this jumpsuit is like wearing PJs. Yes, using the restroom in a jumpsuit feels very strange (because you’re essentially naked) but the comfort factor easily outweighs that brief feeling.
Saturday Morning and Afternoon / Shop Hopping: For a full day out and about, I kept things simple with a tank and my favorite soft jeans. Most vintage jeans like this have zero stretch, but my stomach and digestive system do not do well with that. So when I found this pair that gave me the vintage jean look with some stretch, I was a happy lady. Yes, they bag out after about 3-5 wears, but a quick wash snaps them back into shape.
Saturday Night Out / Dinner, Broadway, and Live Jazz: Ah, another “going out” outfit that feels like PJs. :)
Sunday / Museum, Matinee, and Dinner: We woke up to a chilly, rainy morning, so I cozied up in a sweater and my wool jacket and left my legs exposed so the look wouldn’t be quite so heavy.
Monday / On the Plane: I kept things simple and wore the same airplane outfit as before.
BONUS OUTFITS
I was able to make so many more outfits from the pieces I packed, so how about a few bonus outfits?
And there you have it!
Soon I’ll share my NYC video including our itinerary and recommendations, but in the meantime, feel free to subscribe to my YouTube channel so you don’t miss it.
So tell me, got any trips coming up? If so, care to share any tips or tricks or techniques you’re planning to use to pack? And if you have any questions about how I packed or any of the items I brought — ask away!
xo,
I absolutely LOVE all of your posts – especially the packing ones! They are so succinct and helpful. Plus, your outfits are always adorable :)
Awesome post Caroline! As always :) Thanks for sharing. So Excited for your Youtube channel!!!
Hey Caroline!
I love these packing posts! It always makes me imagine that I’m in some faraway place!
I was just wondering if you have any tips for longer trips! I usually only travel once a year so I end up going for at least a month, if not, more! I would love to see a blog post on this at some stage!
Thanks! :)
You are fabulous. Truly. So gifted.
What an amazing packing teaching/lesson. Your style is impeccable🌺
Thank you for sample & worksheet for planning.
What went into choosing the outer jacket? I always take too many… !
Grateful for Your posts; just subscribed to channel🌺
Love this post! just ordered the Nisolo shoes–super cute. Would you mind telling me how much, if at all, you had your everlane pants hemmed? I have a pair, but am considering getting them hemmed a bit more to match the length you have… hope that makes sense;-)
Hi Jennifer! I actually didn’t hem my Everlane pants at all. You’ll LOVE those Nisolo sneaks! So comfortable. :)
Beautiful! Sounds like a really fun trip! I’d love to know how you think the ZARA shoes fit/feel for all day walking… :)
I’ve been so excited for this post! I’m going to Europe for 2 weeks and I’ve been scouring your past posts for ideas and tips. I am also taking those Everlane pants, and now I’m probably going to copy some of the outfits you’ve put together with them :) Thanks for doing what you do!
I leave for a week in NYC for work in two days! This is so dang timely- love your tips and the travel planner was exactly what I needed to help make sure I don’t take a bunch of extra stuff. Can’t wait for your recommendations!
This is exactly what I needed! We’re heading to Ohio from California for two weeks this Summer and only carrying on so this is exactly the inspo I was in need of!
Hi Caroline ,
Love your post ! May I ask if your away suitcase is the carry on size or the bigger carry on ?
Thanks !
Hi, I noticed these Everlane pants and your Esby wide leg pants are very similar. Do both fit in your wardrobe, or have you let go of the Esby pants? I’m in the market for wide leg caramel pants, so interested in your opinion on these and which you wear. Thanks!
Sadly my Esby pants don’t fit me right now. I’m holding on to them anyway, but they are too small. I’d been wanting to try the Everlane pants, so I just went for it even though it’s a similar color. Even though they are pretty similar, the two pairs of pants do have distinctive differences. To me, the Esby pants are more beautiful (the fabric, color, construction) however they don’t have any stretch. The Everlane pants are a bit more basic, but they’ve got the stretch factor. Hope that helps a bit! :)
I love your posts as usual! I am so close to ordering those Nisolos but I am wondering about sizing. Did you order your normal size or size up? I have seen mixed reviews on the website about this, so I am curious what worked for you. Thanks for the the great post!
I tried on my normal size (7) and they fit just fine. However, I decided to size up a half size anyway (I have a quirk about not wanting my toes don’t touch the ends of my close-toe shoes). So I’d say they run true to size, it just depends on whether or not you like a little extra room. :)
Headed to Portland and Seattle at the end of the month so I need a combination of hiking and regular outfits. This also means more shoes, but still trying to fit everything in a carry on. Luckily workout clothes don’t take up much space!
You’re the best. I’m Alabama so inspired by the simplicity and ease of your style – put together but oh so practical (and lovely!) keep it up Caroline! x
And your toiletries and hair wand fit in the bag too??
They did! :)
Underwear?… I seriously find it nearly impossible to get by with a carry on. Ever. I’m the worst.
I have a big trip coming up, and it always, always posses a unique packing challenge. I’m going to Missouri in the middle of June for a huge church meeting. My outfits need to be very cool (one layer, long sleeve) because we will be outside a lot. It’s ten days long, plus a 1000+ road trip. Laundry is limited, and I may need to change at least once a day! It’s a challenge, but im determined to pack as light as possible!
Oooh sounds like a challenge! You got this! :)
“Once those clothes are on, we bring life and vibrancy to them with our energy.” Soooo true. My whole wardrobe is neutrals and I really don’t miss the color at all, because it makes life so much easier and because I’m colorful enough as I am!
I have that same suitcase and would love to see how it all fit. I can’t imagine getting that much stuff in there!
I was wondering what size you took in the aritzia tank? Thanks!
Hi Cynthia! I got a size XXS.
I just love your blog. Such a treat to to read tonight. It’s hard not to want to buy everything but I love it all.
Going to Alaska soon and terrified of all the bulky rain gear. Inspired by all your outfit choices.
What actually is the colour of your sneakers? Blush rose, or more sand/beige? Unfortunately Nisolo won’t let me even browse their shop because I’m located outside of America…
They arrive looking pretty blush, but over a few months, with wear and exposure to the sun, the natural vachetta leather ages into a lovely soft tan color. Mine are still aging so they still have a bit more of a blush tone, but I can’t wait to see how they look in a few more weeks!
This is incredible!
xx
closettostreet@gmail.com
Love this post, thank you!
What size everlane pants do you wear in comparison to say … your madewell size? I typically wear a 26 or 27 in madewell and really want those everlane pants, but I am not sure which size to go with…
I took the same size as I am in Madewell pants. However, they do stretch out a little, so if you’re in between sizes, I’d size down. :)
I love your packing guide. It’s amazing that everything fit so nicely. Did you have another bag for your new purchases?
Thank you! Somehow everything ended up fitting back in the bag at the end, but I did carry my sweater and coat in the airport, so that freed up a little extra suitcase space. :)
Such gorgeous packing advice! I love seeing into what you bring on your trips. I just adore your effortless style.
xo, Laurelle
This simply is one of the best blog posts ever written regarding packing and travel. Many struggle and stress about packing and a list and a little planning takes the stress away! I have used a list for over 30 years and it really, really helps. I also have additional list sections if the trip includes golf, beach or safari as those take more individual pieces.
Thanks for this blog and I hope it helps many travelers!
We went to NYC in March and saw Hamilton and Dear Evan Hansen! SO good! I saw Mean Girls in November during their pre-broadway engagement in DC and it was hilarious! I’ve been listening to the cast album non-stop since it came out!
Oh my gosh, Mean Girls — wasn’t it fantastic?! I’ve been listening to the soundtrack non-stop too! There are some fun behind the scenes videos with the Mean Girls cast on YouTube — you should check ’em out! :)
Omg, you have such a great sense of humor! (Using the bathroom when wearing a jumpsuit, your digestive system and pants that don’t stretch). Great post, and so perfect for summer traveling. Thanks to you I traveled to Europe and India, 7 weeks, one trip, hot and cold, in one teeny tiny, Wow! Airlines approved, carry on. I was fine, and it sure made moving from place to place easy. Thank you!
Btw, that jumpsuit is darling!
Oh my goodness! Love this post and love that I am now aware of Christy Dawn! My only problem is picking just one, because budget!
What a great packing list! I love having the opportunity to dress a little “cooler” than I do back home when visiting the city. Looking forward to your itinerary – there’s always something new to discover in NYC!
I don’t travel that often but when I do it’s usually a long weekend away with my husband. And even though it’s only for a few days I STRUGGLE with packing so much! Looking forward to using your tips on our next trip.
I also want to say that I’ve been following your blog for a long time now and I’m finally starting to get to a place of creating a solid wardrobe for myself. It can be a stressful journey at times but one of the things I really appreciate about you and your blog is the airiness and lightness and joyfulness that you bring to these topics. It’s not just about clothes but really about a mindset that we incorporate into the other aspects of our lives and that just feels so, so good, and so in touch with where I’m at in life right now :)
Hi! Are the darker joggers you’re wearing the same as the outside voices one you listed? Looking for joggers! Thanks!!
They sure are! I LOVE THEM. Had ’em for three years and they are holding up great!
NYC def a walking everywhere city so comfy shoes first
and a beautiful day and walking there is the best, an awful day not so much
I’ve got no trip coming up but organizing outfits is just as fun for cruising around my city!! That Away x Madewell luggage is so pretty. I am in love!
http://www.hintofgrey.com | Hint of Grey
Thanks for sharing! I love everything <3
Ahhhh such an amazing post with some really gorgeous outfits!
I adore your style of blogging – new follower here xo
Nnedi | iamncxo.blogspot.com
I’m headed to San Diego for 4 days this week & am suddenly S O thankful I stumbled across this post!! I’m convinced I can pack everything into my carry- on now 😍
As usual so inspiring! I pack this same way for work trips when in a big city where it’s fun to feel more like a local at night and on weekends. I do pack, then reduce by 50% with the theory that a new scarf or bag might be in my shop bop! Your pack list is invaluable!-Laurel
What a great post! Love the tips and the outfits.
In terms of tech, what items did you pack? I find I am always with my laptop, ipad, at least 3 extra chargers, cords…ahhh. Its endless. lol
xox,
Savage
Hey there!
I love the Zara woven flats…and they’re something I can easily grab (I live in Europe so can’t get a lot of the clothes you mention). Question: are they actually comfortable/did they break in easy? I haven’t had luck with Zara shoes in the past.
Thanks for your posts….the travel specific are so helpful!
Katy
My best practice when packing is getting a smaller bag. When you have smaller space you’re obligated to get fewer things with you. So, if you still don’t have a travel bag, get a smaller one :)
Hi,
Thanks for your posts! I’m wondering about sizes for the Vetta Capsule apron jumpsuit. I am between sizes 0-2 in Jcrew so not sure what to order for the jumpsuit.
Thanks!
Hi Simone! I’m usually a 0-2 at Jcrew too, and I got a 0 in the jumpsuit. :)