The Things He Carried

How one menswear devotee downsized his wardrobe to make the most of a big adventure

“You need less than you think you do,” says the saleswoman in the fleece zip-up. She is listening to me explain my packing list and her advice suggests that she’s witnessed someone in my predicament before. At my local Mountain Equipment Co-op store, I immediately grab the largest backpack in the place, something no doubt designed for multi-week mountaineering expeditions through the Himalayas. She good-naturedly loads it with a few sandbags and stands by as I struggle to buckle it to myself and carry it around the store. As I sweat and teeter under the weight of a bag that would give a sherpa a hernia, I have an inkling that she might be right.

I’m preparing to embark on a three-month solobackpacking trip through Mexico, seeking whatever enlightenment that might bring. I had initially been concerned about avoiding scorpions and tropical diseases, so the challenge of fitting my closet into a single bag had never even crossed my mind. After years of writing about men’s wear, I not only have a sizeable wardrobe, but I have become quite attached to dressing a certain way. Clothes are not just stuff to me; they are a part of me. The impulse, of course, is to bring everything: beach clothes, hiking clothes, lounging clothes, city going-out clothes, a range of shirts and jeans and light sweaters and outerwear for every possible scenario. Something has to give.

Over the years, I’ve written at length about the value of investing in quality rather than quantity – curating your wardrobe around a few beautiful, wellmade things. I’ve made analogies between the things we buy and the lives we lead, waxing philosophical about authenticity and beauty and aesthetic purity. I believe it all, of course, but now, through some sort of perverse fashion karma, I’m on the brink of being forced to follow my own advice to a degree with which I am uncomfortable.

As I try in vain to gracefully unharness myself from the giant bag, I know what I have to do. I don’t want to be that guy struggling through some foreign airport under a pack twice his size, festooned with dangling sneakers, water bottles and other detritus. I’ve seen this guy, and he looked like he was neither on his way to enlightenment nor having fun. “I need less than I think I do,” I repeat to myself, not really believing it. Then, heeding the gentle advice from the lady in the zip-up, I buy a bag roughly half the size of the first one I’d selected and resign myself to making it work.

Buying luggage is one thing; filling it is another entirely. As my departure date looms, my pile of clothes still dwarfs my bag, which sits empty in a corner, mocking me and my vanity. I enlist the help of a friend, a seasoned traveller who is perfectly happy hitting the road for a month with just a sarong, a folding yoga mat and a pair of light sandals. This degree of austerity both entices and terrifies me – the freedom of traveling light tempered by the anxiety of not being able to dress for every occasion. Sensing the direness of my situation, she suggests we start with something easy.

“How much underwear do I need?” I ask. “Enough for a week,” she says decisively. “Should I bring my favourite pair of socks?” “No. You’ll wear them out or lose them.” And so began my transformation from Stylish Man About Town, to Man With Three Shirts and Two Pairs of Pants. We travel seeking beauty, perspective and inspiration, but in order to find these things it’s often necessary to sacrifice some comfort (the familiarity of daily routines, our own beds, a robust selection of footwear). The longer the trip and the less you bring with you, I reason, the more pronounced the rewards.

After chipping away at the edges, I begin to work on the core of my task. I’ve always liked the idea of men who choose to wear uniforms (think Thom Browne’s abbreviated grey suits and Michael Kors’s blazers and T-shirts, not Canada Post blues), so I take the opportunity to try this approach. I settle on a pair of dark jeans and a pair of dark blue chinos, accented by a rotation of button-down shirts (one blue linen, one green gingham, one a jaunty yellow graphic print). I choose a varsity-style sweatshirt I like but I’m not emotionally attached to, a packable nylon raincoat and some long underwear for chilly nights.

Five pairs of shoes had initially seemed reasonable, but practical realities suggest that number is, in fact, ridiculous. I have to make do with two. Alongside my trusty runners, I console myself with the purchase of a new pair of tough suede Chelsea boots. In the name of beauty, perspective and inspiration (plus, new shoes!) I decide I can stand to be underdressed for formal occasions, should they arise.

As I look at my travel uniform laid out before me, I like the person it suggests. He is spontaneous but stylish, practical but adventurous – a sort of Indiana Jones by way of J.Crew – and a man who values authentic experiences and beautiful things in equal measure. I haven’t fit my outer self into my backpack after all – I’ve created a new one. And I quite like the way he dresses.

Click to read at Globe and Mail