There are tons and tons of lists/advice articles for packing out there. They insist that X number of shirts are necessary, or Y different types of shoes, or a combination of ABC are absolute essentials. But in my extensive travel experience the most important things for packing are honesty and self-reflection. Vacations and travel tend to be the fulfillment of fantasies–you’ve been dreaming of going to Costa Rica, or Tokyo, or California for years and now, you’re finally going! Dream come true! But it’s important to remember that when you’re finally enacting this fantasy, you’re still you! So: the most essential things for packing: are honesty and self-reflection. Being honest about what you like to do and how you like to spend your time will lead you to the most important items to pack.
For example, if you know you’ll be relying on public transit, but you don’t want to arrive at your hotel(s) sweaty and gross from lugging a ton of suitcases around, pack one you can handle by yourself with ease. You DO NOT want to be the person holding up the bus departure because you can’t wrangle all your luggage. If you hate the idea of having to wash your socks in the hotel sink, but re-wearing a shirt is NBD, pack one less shirt and three more pairs of socks! If it’s important to you that you have a ton of outfit changes, that means multiple, heavy suitcases, be realistic about the need to pay others to help you haul your stuff around. There’s no one-size fits all when it comes to packing and deciding what is truly the most important to you is what really matters.
I almost always pack too many “fancy” items when I travel. I like to think that I’ll spur of the moment go to the Opera, or a hip restaurant, or get invited to an elegant party. But in all honesty, that pretty much never happens. It’s smart to bring one “nicer” outfit, but I have never needed the two or three fancier dresses I tend to pack. A black or other dark color jersey dress that folds down to nothing and won’t get wrinkled, is a much smarter option for me than the full-skirted strapless dress I was tempted to bring on my last trip. Sure, it’s a super cute dress, and I do wear it on the reg, but it’s a bit overkill for hours and hours of stomping around foreign cities. And Dry Clean Only is a crap strategy for traveling.
When voyaging to foreign, new, or unknown places I’ve found it’s best for me to bring favorites: favorite shirt, pants, shoes, whatever. Yes you run the small risk of losing them, but it’s nice to have the comfort of your favorite articles of clothing when surrounding yourself with the new and unfamiliar. It’s like armor.
So when packing: think about how you really live, what you genuinely like to do, and the actual likelihood of that spur of the moment Opera visit. While travel is full of new experiences, most people tend to travel like they live, whether that means fancy drinks on a yacht or beers on the dock. If you actually do decide to go somewhere extra-fancy and you’re missing the requisite clothes, you can always go on a quick shopping trip. Unless you’re in the heart of the Amazon you’re not going to be bereft of options and a shirt bought in Denmark makes for a great story later: “Oh this old thing? I got it in this amazing boutique in Copenhagen…”
And besides at the core, the only thing you really need while traveling is your passport and wallet.