Hike Fashion: On Dressing Well for the Great Outdoors — PART 2 – Habilitate

Image credit: Austrian National Library on Unsplash

Earlier this week I wrote about walking the West Highland Way and how I couldn’t stop thinking en route about outdoor clothing generally being so…well, not to put too fine a point on it, but…ugly. 

I also listed some of the things I wore along this roughly hundred-mile journey. In a nutshell, it involved a lot of flannel, shorts, and old T-shirts. Basically, anything Reese Witherspoon would have worn in Wild, although she appears to have been saved the indignity of wearing a midge net. (I’m not kidding about the Wild thing, by the way. As part of my clichéd search for enlightenment on this particular trip I rewatched the film one evening along the way and was reminded just how good the costuming is. I remembered the Danner boots, of course, but I’d forgotten that just about everything else she wears looks fantastic too, from her flannel shirts down to her hiking socks. Even her pairing of a clunky digital watch with a silver bangle is a look I fully intend to copy on a future outing.)

Even so, my Cheryl Strayed cosplay didn’t feel quite sufficient. Provided you’re willing to do a bit of digging, there is more than enough out there to merit a follow-up article listing some of the other items I don’t own but have my eye on. Despite me decrying the general state of outdoor wear last time, there is no question that there’s also a lot to be excited about. The rise of Gorpcore as a trend in recent years has shown time and again how much great stuff is being made and just how good it can look. Plus the public appetite for this kind of thing seems to be at an all-time high. You can’t throw a stone in my neighbourhood these days without hitting someone wearing North Face or Arc’teryx.

So, since my own thinking about the subject started a few years ago when in a pinch I couldn’t find hiking shoes that weren’t hideous, let’s start there. The gold standard for me has always been those aforementioned Wild Danner boots, officially known as Mountain Lights, which unfortunately come with a hefty price tag, clocking in at around £400. The best-looking affordable options I’ve seen have been by Alico Sports, though these can be tough to get your hands on depending on where you live. On less demanding hikes I’ll personally just throw on my Blundstones or L.L.Bean duck boots, which tend to go for somewhere between £150 and £200 and usually get the job done. I’ve also seen a few guys use Red Wing work boots in the same way, though, of course, those are also on the pricier end. The other canonical boot choices that are easy on the eye are the Paraboot Avoriaz and the slightly more outré Yosemite, as well as various models by brands like Grenson, Fracap, Diemme, Feit, or even Viberg if money is no object.

Image credit: Ellena McGuinness on Unsplash

If boots aren’t what you’re after, there has probably never been a better time to find fun and interesting trail-running or walking shoes by everyone from outdoor stalwarts like Salomon and Merrell to lesser-known brands like Norda, or the Nike offshoot, Gyakusou. It probably goes without saying though that these often outlandish silhouettes definitely won’t be for everyone, although for my money they sure beat the drab iterations of brown that formerly dominated this particular category. Then there are the equally divisive sandal options, for which Teva, Chaco, and good ol’ Birkenstocks are always solid options, and even more so now that wearing socks with sandals is encouraged, especially in this context.  

Working our way north up to trousers, I tend to use any workwear-adjacent pants for hiking purposes, including my trusted Carhartts and Dickies. And for warmer days, I’ve already professed a love of Baggies and cut-off shorts on many occasions, though perhaps it bears repeating here. If I were buying stuff from scratch, however, I would probably go with something from Stan Ray, Taylor Stitch, or even J.Crew since you can’t really go wrong with them these days. For shorts, I’ve always hoped Patagonia would bring back their original Stand Up shorts (you can still find them on eBay), but I’ve also long had my eye on some Birdwell’s corduroy shorts or something by Comfy Outdoor Garment.

I find outdoor activities are a great way to give old shirts a second life. Never has a raggedy T-shirt looked better than out on the trail under a similarly well-travelled flannel or fraying Oxford shirt. If you’re looking for tees that look like they’ve seen some things right out of the box, maybe the best ones I’ve laid eyes on are by Imogene + Willie. In an entirely different vein, I’m always intrigued by the stuff that Vollebak comes out with, especially when they advertise T-shirts made of carbon fibre, ceramics, algae, and, my personal favourite, ‘garbage’. Then for flannels, most of mine are thrifted or from L.L.Bean, though Pendelton is another stalwart option, ditto RRL, Filson, The Flat Head, and really any workwear label you can shake a stick at.

Image is my own / All rights reserved

Then, for layering and outerwear, if you want something classic you can never go wrong with a beat-up sweatshirt, a hardy fisherman’s sweater, a rugby shirt, or the tried and trusted fleece. While Patagonia wrote the book on fleece (I probably own one too many of them myself), there are innumerable other options out there from Uniqlo all the way up to Drake’s, these days. You also have a bunch of great jacket options too. For ages, I’ve wanted to get something from Rocky Mountain Featherbed, although I’m also very keen on some UK-based brands like Yarmouth Oilskins, Everyday Garments, James Darby Clothing, and Fuzz Garments, as well as this one from Adsum or the Bryceland’s Foul Weather Anorak.

As far as the rest goes, I’ve tried a few different brands of hiking socks over the years, but so far ones by RoToTo are my favourite. I also know a lot of people like American Trench and Wigwams, although if you don’t want to spend too much on socks you always have Hanes and Uniqlo as budget-friendly options. While I’ll usually just wear a bucket hat or cotton baseball cap while walking, getting repeatedly soaked along the West Highland Way got me interested in buying a water-resistant cap for the first time. I know menswear illustrator Simon (aka Deliberate Indifference) said he liked the Montbell Gore-Tex cap in our interview earlier this year and I’ve seen similarly styled ones by brands like Goldwin and Arc’teryx. For colder weather, there are a million options to choose from as far as knit hats are concerned, but if I were to buy one right now I’d probably go with something from Heimat for this purpose. I’m also a sucker for bandanas, with my favourite examples usually coming from Kapital, although I’ve seen a tonne of cool ones online in places like Suusco recently.

And, finally — the true friends of any outdoorsy type — backpacks. Usually, when I’m travelling sans wheely bags I’ll go with a North Face backpack I got as a gift years ago but if I were buying one from scratch right now I would again be tempted by something from RRL as well as Epperson Mountaineering, Kletterwerks, or some of the ones from Mystery Ranch

Image credit: Annie Spratt on Unsplash; Needpix; National Parks Gallery / Public domain

If you’re looking for a rule of thumb as for dressing well out in nature goes, though, I’d say anything in the realm of workwear, militaria, and, of course, good ol’ fashion Gorpcore generally flies. A bit of wear and tear is also always welcome. You can’t go wrong looking for inspiration from old-school rock climbers, mountaineers, or the like (this GQ profile and this Put This On article give some great examples). Alternatively, if you’re of a more experimental bent, just dive into some of the colourful and creative stuff that’s on the scene at the moment. There’s maybe never been a better time to dress in an appropriately adventurous way while heading out on the trail. For every bit of grim and uninspired rain gear out there someone is reimagining what a cagoule or hiking shoe can look like.

And, if you still need further inspiration, why not check out the fantastic offerings by some of the places I haven’t yet mentioned, like Bradley Mountain, Snow Peak, And Wander, The Bureau Belfast, Huckberry, Houdini, Gramicci, Manastash, Nigel Cabourn, and Cloth & Cut. For more outré outdoor-ready stuff, see F/CE, South2 West8, Monitaly, and Nanamica.

Until next time, I’ll see you out on the trail. Happy hiking!