Unpacking the packing strategy
Balancing personal style with the practical realities of traveling
When my husband and I first began dating, he was working on Wall Street and I was living on the Upper West Side. One of our favorite weekend activities was to walk the 6 miles from his office to my apartment, varying our route every time to unearth the many cultural, shopping, and food gems (including determining where to procure the best chocolate chip cookie - Birdbath Bakery, RIP) throughout the city. Early on, we affectionately called the activity “urban orienteering” given the many hours spent on our feet and the meandering way in which we’d arrive at our destination. As our relationship grew, we quickly learned that our passion for discovering New York on foot extended to cities across the globe; we started enthusiastically pounding the pavement across Europe and Asia, typically leaving our hotels early in the morning and not returning until late in the evening, after a delicious meal and a round of drinks at a locally-recommended cocktail bar. To me, there’s something so romantic about roaming a city, rubbing elbows with locals, observing and reflecting on the myriad of subtle culture nuances, admiring the centuries old architecture blended with modern forms, and wondering if someday, when we’re older, we could see ourselves with a small apartment around the corner.
When preparing for our “urban orienteering” vacations, packing has always felt a bit daunting. I want to feel like my suitcase is filled with pieces that reflect my personal style, but also need to be completely pragmatic with my choices given the multitude of miles on foot each day and the way in which temperatures vary from sunrise to peak sun to sunset. As much as I would love to have the “perfect outfit” each day, I’m not willing to give into the disruption that may cause, and the tradeoff of missing out on discovering something new while out and about. After my husband and I spent 12 days in Japan this past October, I can finally say (after many, many failed attempts over the years) that I am the closest I’ve ever been to mastering the “art of packing” for extended trips - getting the most use of all items and feeling well-prepared for an array of activities.
As I reflect on what made my packing more successful this go, I have to attribute it to some principles I embraced that ultimately served me well.
Stick to a color palette where everything can be mixed and matched without having to overthink it.
For this trip, everything in my suitcase was black, white, gray, navy, or denim. This made outfit combinations feel plentiful and it was easy to add and remove layers, which was helpful for the evolving weather forecast over the 2-week period.
Don’t leave home without your hero pieces.
Your hero pieces are the reliable items you can wear time and again without much thought. They allow you to transition from activity to activity while feeling completely comfortable, but they also capture core elements of your personal style.
On this trip, my hero pieces were:
Medium-weight, neutral colored sweater: My La Ligne Marin Sweater (also loved by Jenna Lyons and countless others) was undoubtedly the trip hero. This was tied around my neck, wrapped around my waist, or layered on top of a tank, t-shirt, blouse, or dress when there was a chill in the air. During our trip to Italy last year, I used a charcoal gray Jenni Kayne Alpaca Cocoon Crewneck Sweater for the same purpose.
Comfortable, yet nice restaurant-appropriate sneakers (if you’re really in a bind): My go-to on pretty much all vacations has been my Golden Goose Ball Stars. I can walk 12+ miles per day in them without stressing and they have a nice durability when the weather turns. Though I prefer to wear a nicer pair of shoes to dinner, these can still get you into a restaurant when you’re truly in a bind and my personal opinion is that they look nicer than a pair of athletic shoes.
Cotton t-shirts in a few neutral colors: I’ve shared previously that my favorite t-shirts are from Teller Shop in Los Angeles. Over the years, I’ve stocked up on white, black, navy, and tan, and find that I always have at least 3 of them packed for a trip. The shirts are high quality and easy to dress up if needed.
Black, straight leg jeans: Black jeans are another hard-working vacation piece because they’re typically appropriate for any activity. When wearing them to a nicer dinner, I’ll incorporate a belt and add sandals or heels. They also appropriately hide any city grime and still manage to feel slimming after you’ve eaten your body weight in sushi.
Silky pants: These are perfect for the plane, for days when you’re traveling between cities, and they’re also easy to dress up given the sheen. Donni was my choice this trip.
A lightweight black dress: This was ideal for dressier activities and I could layer my sweater and jacket as needed based on temperatures. The Rachel Comey option I chose was more conservative to match dress codes in Japan. I liked the versatility because I could wear it on the shoulder, off, and with one shoulder. I added a belt to give it more of a defined silhouette.
A leather jacket: I’ve always found a leather jacket to be another piece that’s easy to dress up or dress down, but consistently feels stylish. I also love the fact that it is warm enough on its own during a cool night, but if the temperatures start to drop, the addition of a sweater underneath makes it cozy.
A cross-body bag: I only bring one bag on these vacations, as it’s just easier to manage. A cross-body flap bag can fit the essentials - wallet, phone, hotel keys, sunglasses, and hand sanitizer.
Leverage accessories to elevate looks for evening and create outfit diversity.
When there wasn’t time to stop at the hotel before going to a nicer dinner, I would add a pair of oversized earrings and a necklace to dress up the look. Using jewelry and belts also differentiated looks when I was repeating an item.
Try on everything in advance.
I don’t know why, but I personally really dislike going through this part of the process, but I forced myself to do it in preparation for Japan and it really paid off. As I tried on all of the outfit combinations, it allowed me to edit out pieces that wouldn’t be as versatile. It also saved me money in my vacation prep because there were pieces I purchased for the trip that definitely seemed better in my head than in reality when styling.
Don’t stress about preparing for the “worst case” weather scenario, but do prepare for downsides
The biggest weather risk on our trip was rain, and as the days got closer and closer to our departure, the forecast was ever changing. So as not to dedicate a large portion of our suitcase to the elements, my husband and I game planned what we would do if we woke up to a torrential downpour that lasted multiple days. We knew that if we really needed to buy gear, we could go to Uniqlo or Muji for cost-effective options. We also considered this from an itinerary standpoint in terms of how we would make adjustments to our plan for the day.
Adopting the aforementioned principles resulted in nearly all pieces in my suitcase being worn throughout the trip. It also allowed me to save space for some purchases and take advantage of the favorable exchange rate, in addition to bringing home a nice assortment of Japan’s iconic KitKat flavors to share with friends and family.
Fingers crossed I can listen to my own advice for the next trip.
Happy travels,
x jz
Images | 1 - 6 | @b.g.mckay
I’m all about packing cubes and color schemes. It makes packing so much easier. My Marin sweater was also my most versatile and worn item on a recent trip.
Great article! On a recent trip I packed all black and white and found it so easy to adjust outfits to the weather etc. packing in colour stories has been huge help.