Unconventional Life Hack: Pack Your Suitcase Irresponsibly

ruby redstone experimental packing style

This time last year, I was laying on the beach in Portugal reading Sloane Crosley’s essay, “Up the Down Volcano,” in which Crosley declares that she likes to travel purposefully unprepared, tossing herself headfirst into the unknown without the protective comforts of blister Band-Aids or anti-diarrheal tablets. “That’s ridiculous,” I muttered to myself, before pausing to survey what I was doing as I read–attempting to shield myself from the sun using a fully sheer tulle dress dusted with velvet polka dots.

The very same dress had earned me looks of disapproval from more modestly dressed tourists on a hike up to a castle earlier that morning, but I had been too busy trying to angle my feet so that the pearl studs hanging off my sandals wouldn’t chafe my toes to notice. Back at the Airbnb that night, I rifled through my suitcase in search of physical proof that I was the well-prepared, seasoned traveller I believed myself to be. Instead I found two pairs of hot pants, a bonafide ball gown, and precisely nothing resembling a sneaker. I had spent almost a year planning for a mammoth, month-long trip that would take me from sunny Lisbon to my college graduation in Northern Scotland, through Russia and into Southern Siberia. I had sifted through the websites of enough budget airlines to start my own travel agency and run out to Duane Reade to pick up “just one more thing, just in case” at least a dozen times, and yet somehow my suitcase looked like it had been packed by a toddler running away from home.

Over the course of the past year, I have realized that being a good packer and being a practical packer are two very different things.

Allow me to defend myself for a moment here. On paper, I’m really good at packing. I haven’t checked a bag in years. I have enough mini bottles of beauty products to moisturize a colony of Glossier-loving mice. I always have ample pairs of underwear for reasons best explained by this meme. It’s when I unzip said carefully folded-and-rolled carry-on that things get…questionable. I made it from Portugal to Russia and managed to dress appropriately for a variety of events that included a black-tie ball and a pilgrimage into the Ural Mountains. (Okay, I did wear a bikini top as a shirt a few times, but mostly it was fine). When I arrived for Christmas morning festivities in snowy Utah dressed in what I thought was a perfectly suitable pair of blue knit bloomers and matching Fair Isle sweater only to be laughed at (good-naturedly, of course) by my family, I began to catalogue the disparity between the things I chose to pack and the things everyone around me chose to pack.

Over the course of the past year, I have realized that being a good packer and being a practical packer are two very different things. When I posited this concept to my best friend, she reminded me of a trip we had taken together where she had bragged about her ability to stuff a tiny bag full of black-and-white pieces that would theoretically function as a simple, crisis-proof wardrobe. When we arrived, she instantly found herself numbed by boredom with the things she had packed, and we spent the trip sharing things from my suitcase.

I’m curious about this phenomenon that occurs when we pack to travel–this desire to pare our style down into something sleek and palatably inoffensive. Is it a product of too many camel coat/white tee/black jeans “capsule wardrobe” packing lists? Or is it a deeper fear of sticking out in an already unfamiliar place?

While I’m no closer to finding an answer to this question, I have embarked on a one-woman battle against packing boredom. The solution? Filling a suitcase with whatever the heck I want and paying no mind to the practical concerns of pattern-clashing, over/under-dressing, or comfort. I used a family trip to Italy this month as an excuse to throw caution (and, um, the weather forecast) to the wind and really take my theory to the streets. Before departure, my sister asked for a copy of my packing list to cross-reference with her own. I sent her a screenshot from my iPhone notes and she responded with: “wtf. NOT helpful!! I can’t make a single outfit with anything on this list.” Thus fully satisfied with the inauguration of my experiment, I set off for the airport, camera loaded to document my impractical journey.

Photos provided by Ruby Redstone.

Ruby Redstone

Ruby Redstone

Ruby Redstone is a writer, stylist, and art historian (no, seriously) from New York City.

More from Archive