I think we can mostly agree that packing is a pain. Who likes hovering around a wardrobe, trying to imagine what you might be wearing two weeks ahead for a totally different climate in a foreign place? And the absolute worst part of packing is the even-worse anticipation of unpacking.
But thanks to several years a few hundred thousand miles of frequent flying, I now have my suitcase skills down to a science, so while it might still not be a pleasure, it’s a bearable pain.
I started thinking about what I was going to bring for a two-week trip across Australia a few days in advance. On my itinerary: Sydney with my buddy Nathan, a road trip up to Byron Bay, and a weekend trip to Melbourne. So there were a couple different vibes to be packed into two checked suitcases.
A few days before departure I clear a new rack in my closet that’s reserved for items I know I want to bring. Each morning as I go through my clothes to get dressed, whenever I spot something that I know would work, I put it aside. This way it’s an organic process, rather than a frantic rush going through everything the night before (which is still slightly better than morning of, which I’ve done a few times).
For a long trip like this one, I don’t pack by outfit, but rather by category: pants are one, wovens another, along with knits, accessories and workout gear. It works to stick within a color story, that way whatever you pack will work with everything else and you can be a little more spontaneous on the day you wake up about how you want to put your outfit together.
I was working with a mostly neutral color palette for my daytime basics. It’s good strategy to pack items that aren’t repeats of one another: instead of two pairs of blue jeans, pack one blue and one white pair or one with a different wash.
The Fall season is in full swing down under, so while it’s just starting to warm up in New York, it’s cooling down in Sydney. I put aside seven pairs of pants: three pairs of denim, three casual chinos and a pair of versatile joggers, each with a color variation. I didn’t know whether I’d be able to do laundry this trip, so I brought enough shirts and sweaters to have a fresh one every day.
You never know when you might end up in a Jacuzzi or a fancy party, so I always pack a swimsuit and a suit jacket, just in case. A white and black dress shirt, along with a classic grey blazer, go with everything and look cool with dark denim.
Lastly, I lay out shoes and accessories. I wear mostly sneakers these days – even with suits – but I like to have at least one pair of dress shoes just in case. Also put out my Birkenstocks (because: German) and pool sliders (because: Bondi).
When it comes time to putting everything into the suitcase: think of it like a game of Tetris. I fold the bigger items first: the pants, the knit sweaters, etc. then stuff in the sides with underwear, shorts, and swimsuits. Maximize every inch of space.
Another trick I’ve learned over the years is to keep your wovens (dress shirts, blazers) on their hangers and pack them last. This decreases fold lines and makes it easy to unzip and hang them up as soon as you’ve reached your destination.
It’s always great if you can fit everything into just one checked bag, but if you’re headed for a long trip, sometimes two is inevitable. I keep most clothes together in one and divide the other with shoes, belts and anything else the TSA might pull you out of line for.
Now just hope your bags arrive where you do.