When I have a vacation on the books, I begin packing approximately 15 days in advance. I haven’t always been this way. In my early twenties, I used to wait until the last possible minute to pack, and never had the adage “wherever you go, there you are,” rang so true. Because there I was, leaky shower caddy in my carry-on, outfits kind of wonky, taking a cab to the local Target for underwear, and asking my friends if I could borrow their sunglasses because, for some reason, mine were always broken or missing. When I am messy, I carry a lot of stuff with me; my personal chaos feels like carrying around a grouchy, unreliable travel companion who could betray me at any turn. Broken sunglasses and missing underwear usually turned out fine; the worst part was the redundant disappointment each time.
A couple of years ago, after a trip Upstate where I actually cried because I hated all the clothes I had packed, I resolved to never feel that way again. On vacation, I can be anyone I want — someone who throws on sneakers and goes for a walk every morning and always has the perfect shade of lipstick for dinner, for example. There’s no reason to be my messiest self, and before my next trip, I was going to become someone who reveled in packing, and guaranteed herself a good time. Someone who had zipped up her suitcase so long before takeoff, that upon arriving at the hotel she can’t even remember what delights await her inside.
Changing perspective takes time, as does running errands and ordering stuff online, which is why now, as a reformed woman, I always give myself at least two weeks to pack. Vacations have never been the same. (There’s less crying, for sure.) Here’s my two-week packing plan that, I contend, is the only way to prep for a trip.
Two Weeks Before Your Trip
For me, the first step in packing for a vacation is asking myself the ultimate existential question (Who am I?) but with a limited focus: …on this trip? Starting two weeks before means I can marinate on that question before making a packing list. There are so many types of trips, and so many people I or you could be. You could be a divorcee going on a tropical vacation. You could be newly sober, going on a work trip to Dallas. You could be an artist, returning to your parents’ house to deal with a complicated family situation. You could be half of a married couple, going to your first swingers’ retreat in the Poconos. I could be someone who regularly journals. Yes, you will always be yourself, but who else? What are some new things you want to try? How do you want to feel?
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The responses to these questions should allow for a bit of fantasy, even under the worst circumstances. There are appropriate outfits and accessories for each one. You may have to buy something new. You will definitely need a toothbrush and underwear, and you might as well set them aside. I’d recommend getting some packing cubes (you can find them pretty cheap on Amazon). Start making lists. Making a list for yourself might feel like another chore, but ultimately it is an act of love.
Say you really do need to travel for some emotionally difficult family situation. Think about what would comfort you during this time. Maybe it’s a cozy new sweater, or perhaps a bright red lipstick. It could be a sketchbook, a vibrator, or your favorite pair of sweatpants. When you have five minutes to yourself, you will be thankful that you had the foresight to take care of yourself. Two weeks will give you enough time to test out lip colors, launder your sweats, or order that cozy new sweater. If you need to stop thinking about this situation for a while, a two-week packing strategy gives you space to do that.
For me, the clothes always seem to be the toughest thing to wrap my brain around, so I always start there, and pick a color palette. For a recent trip to Mexico, I only packed three colors: white, black, and various shades of blue. I know this sounds incredibly boring, but it is so useful for outfit-planning and staying in “character.” I don’t wear blue a lot in my New York life, but the tan and extremely blond version of myself in Mexico wears it constantly.
For that trip, once I settled on the palette, I looked for the gaps in my wardrobe and made a list of what I still needed: a couple dresses for dinners, another swimsuit (or two), some shorts. Then, I went online.
Pre-vacation shopping can be a fool’s errand unless you have strict parameters (including a specific window of time, and a color story). Sure, the high waisted red bikini is cute, but it’s not in the palette. This super on-sale dress is nice, but it won’t arrive until the day you leave. Don’t over complicate things or opposite-Kondo by buying too much new stuff. You run the risk of buying clothes that don’t fit and need to be exchanged before you leave. This will only be extra work and stress for you. On that note, try on everything, new and old, before you pack it. Take the tags off the new clothes you’re keeping and wash them. Fold them in piles (like with like) and resist the urge to wear anything new before you depart, lest you spill something on yourself.
That’s right, you still have something like seven work days to go, and clothes are already being piled in a suitcase. Vacation just feels closer, doesn’t it? This is also part of the appeal.
One Week Out
If you travel frequently, you may already have a travel kit with your essential toiletries and makeup. Take all this stuff out and make sure there are no empty or drippy bottles. Do you need to get travel size containers for your face wash? Do you need any kind of special makeup (tinted moisturizer with SPF, or waterproof mascara, for example)? This is your second shopping list, and a good time to pull together a travel first aid kit to pop in your carry-on. Advil, bandaids, a mini Evian face mist, a nail file, extra contact lenses. You want to keep these things on or near your person at all times, so if your bag gets lost, you aren’t screwed. A small Tupperware container is an excellent way to store and carry extra charger cords. Throw this in your carry-on, too. Yes, now you are the person with extra chargers!
Then, think of miscellaneous comfort items, like a journal, a travel candle, linen spray (a travel necessity! I swear!), and sheet masks, and pack those in their own separate travel cube. This will feel like a little care package from home when you open it. This can also be the first thing you do, packing-wise. It might help set the tone of the rest of your packing journey.
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A few days before…
Though you’ve been preparing to pack for over a week, it is now time to start actually packing.
As you’re folding, make a mental note of how and where you want to wear each item. “My strategy for packing cubes is that I organize each one by the destination I’m going on — bathing suits and rompers in one, and sweaters and long sleeve tees in another,” says Ally Betker, Away’s editorial director, and the Editor-in-Chief of Here Magazine. (I love Away Insider Packing Cubes, because I like that they match my luggage. It’s really that simple.)
I also recommend writing down your outfit plan so you don’t forget it when faced with a bag full of clothing you barely remember packing. I use a classic Moleskine journal and write everything down by hand, though I have heard good things about Packr, an app that gives suggestions based on your itinerary. Be sure to use this time to fantasize about how you want to feel on this trip. When will you find time for yourself? What will you be wearing to breakfast after a big night out (or in)? If your trip is more than five days long, give yourself the gift of a little time with it. Enjoy it. Put some music on and have a cocktail. This should be fun. If nothing else, it should make you feel superior to a younger, messier version of yourself.
The goal is to have your suitcase zipped up 24 hours before you leave for the airport so you can worry about things like taking out the trash, finding your passport (just kidding! You should’ve done that months ago!) and generally not rushing. I know this might sound tedious, and I understand not everyone has the time (or a robust enough wardrobe), but if you can swing it even once this year, for one big vacation (which I hope you get), I recommend packing two weeks in advance. The glory of packing in such a slow, meticulous way, is all in the details. Not only do you have everything that you need to take care of yourself and have fun, but you also have Bandaids and a spare charger for when your friends inevitably need them. Importantly: You will not be the friend needing all the things.
When you arrive at the airport with a well-packed bag, and not sweating through your tee-shirt because you had to sprint to the gate after scrounging for your SPF at the last second, you unlock the last and possibly best benefits to this method: Your trip feels longer. You feel more rested. You feel like your best self — the one with the right shoes for running and the perfect lipstick for dinner. And isn’t that what vacation’s all about?