Hike Fashion: On Dressing Well for the Great Outdoors — PART 1

As I type these words I’m busy nursing the bruised feet and sore muscles I was recently dealt by the West Highland Way. A week or so ago I walked all 96 miles (154 km) of it in six days, which meant that between the starting point just outside Glasgow in Milngavie and the finish line at the base of Ben Nevis in Fort William, I had a lot of time to do nothing but walk and think. 

This was the whole point of doing the walk. I took it on as a pilgrimage of sorts; a journey of self-discovery in which the physical tracing of a route on a map somehow transforms into a similar exploration of the soul. It’s the kind of trip you embark on expecting hefty revelations, in other words. 

In my case, however, rather disappointingly, pretty much all I thought about was clothing. It turns out that my soul has no great depths to plumb and that any attempt to do so turns up little apart from half-formed theories about dressing habits.

To wit: The question that I kept coming back to as I passed fellow hikers slogging along the trail — covered, as I was, in midge nets, rain paints, and oversized backpacks — was this: Why is it so hard to find outdoor clothing that looks nice?

This dilemma was first brought home to me a few years ago when I was looking for a pair of hiking boots that, to put it plainly, wasn’t hideous. As someone interested in dressing well whenever possible, aesthetics were my primary consideration, followed shortly by comfort and price. At the time, though, this seemed a nearly impossible request to service without hundreds of pounds to spend. So, short on time and especially on money, I settled for the least offensive-looking pair I could find on Amazon. The boots I got proved a surprisingly fortuitous and long-lasting fit in the end. I even wore them halfway across Scotland on this very trip. Yet the surprising difficulty of finding a nice-looking pair of hiking shoes has stuck with me.

It’s a predicament that proves no less pronounced in the realm of clothing. Visit nearly any mainstream retailer of outdoor wares and, in my experience anyway, you will find it nigh on impossible to locate a garment you would willingly add to your wardrobe under any normal circumstances. Unsurprisingly, the same proves true out on the trail or campsite. Look around and you’ll be hard-pressed to find anyone who isn’t dressed in the most purely utilitarian (and therefore somewhat uninspiring) wares.

Now, I don’t mean to sound judgemental here. People can, of course, dress however they darn well please while in the great outdoors. We’re talking about a context in which, more than most any other, practicality is the prime consideration. When your priority is staying warm or dry, out of the sun or just in nature, the last thing most people care about is what they look like. And they certainly don’t need a snooty menswear blogger blagging on about how they haven’t sufficiently glammed up their gear. 

There are, however, people for whom, like myself, the question of dressing well even in this context is a real consideration. I’ll also say that while some may raise the aforementioned point about the inevitable primacy of practicality when dressing for the countryside, for me a sense of aesthetics is inextricably bound to the experience. Surely part of the reason you answer the call of the wild to begin with is to seek out nature’s beauty. Aspiring to have a similar aesthetic sense animate the clothes you wear while doing so seems only fitting to me (albeit by no means necessary). 

So, in a context where you want to dress nicely on a hike or similar but the clothes sold for such purposes usually don’t appeal to you, what do you do? As is so often the case with similar clothing-related quandaries, you inevitably have to spend some time seeking out the stuff you do like. 

Luckily for me, time was all I had on this trip so it was exactly this — the kind of stuff that does look good in outdoor contexts — that I kept mulling over in lieu of self-discovery as I trudged along the West Highland Way. So what I missed out on in psychological breakthroughs, I gained in pointless sartorial musings.

To begin with, let me tell you about what I packed for this self-same hiking holiday. As with any vacation, I tried to take the best stuff I could for the context in question all while being mindful of the size- and weight constraints of my luggage. While I was paying a travel company to haul most of my baggage between stops (I am firmly of the glamping school of outdoor vacationing), I still tried to keep it as light and simple as possible since I would inevitably be wearing or carrying some or all of it at various stages. This meant I had to leave usual walking staples like my Barbour Beaufort and Retro Pile fleece behind.

Then there was the aforementioned consideration of practicality. There were some factors that couldn’t be avoided: This being Scotland in the summer, I would, among other things, inevitably get cold, rained on, and attacked by midges. That meant packing some rain gear and lighter fleeces, most of which I bought from Patagonia a couple of years ago (apart from the inevitable midge nets, which to my knowledge are not currently featured among that particular manufacturer’s offerings).

Those necessities being largely dealt with, I had more wiggle room with the rest. Having never found any sweat-wicking, performance shirts I like, I’ve always worn old T-shirts on hikes — in fact, the more ragged the better, I say. With these I’ll usually put on a similarly well-worn flannel or chamois shirt before piling a fleece or rain jacket on top of that if needed, which is exactly what I did on this trip.

As far as trousers go, in summer I inevitably wear cut-off shorts or Baggies, while in cooler weather I typically reach for some old military fatigues, a pair of chambray pants I bought from Uniqlo, Carhartt double front pants if it’s properly cold, or my polycotton Dickies if it’s wet out. I packed all of the above for this trip, apart from the Dickies since heavy-duty, purpose-built rain pants were called for on this particular outing (I obviously got soaked down to my toes regardless — we are talking about the Highlands, after all).

For the rest, I already mentioned my reliable bargain boots, which I’ve sadly had to retire after their years of loyal service on this most recent 100-mile walk. I also took along a pair of similarly trail-worn Nike Pegasus running shoes and my oldest pair of Vans Authentics, which I only ended up wearing in the evenings and on the trains bookending the journey. Alongside these footwear choices came every pair of hiking socks I own, most of which are made by RoToTo and purchased from Epitome of Edinburgh. Then there was a beat-up baseball cap (one of many well-loved ones I use for this purpose), a bucket hat that proved easy to squeeze inside a backpack or trouser pocket, and a cotton beanie also gotten from Patagonia some years ago. Finally, I tossed in a handful of trusty bandanas and my Casio G-SHOCK with a little compass attachment on the strap.

Now, whether or not all of this counts as especially attractive or stylish is, of course, a matter of opinion. I certainly gave it the old college try given the circumstances, but part of why I kept pondering questions of style was that I wasn’t entirely satisfied with the stuff I was wearing on any given day. While I like the look of almost everything cited above — the old boots notwithstanding — there is a whole world of gear that I’d add to the mix in an ideal world (I am, alas, not unlike when I first bought my trusty albeit somewhat unsightly boots some years ago, still a bit skint). 

So there remains a lot more to consider when thinking about the kind of things that constitute stylish attire alfresco. We are, in other words, not all the way through this sartorial spirit quest. But since the length of this post is already pushing well beyond the capacity of any reasonable attention span, I’ll save the rest for a second instalment later this week. So, to add a cliffhanger that feels appropriate for such outdoorsy subject matter, be sure to tune in on Wednesday if you’re interested in reading about all the other outdoor clothes I have my eye on.

You can read PART 2 here

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