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How to Dress Like an Outdoorsman

Searching for a look that reflects your outdoor lifestyle? Here’s how to nail the ‘rugged outdoorsman’ vibe and build an adventure-ready wardrobe of iconic yet versatile style staples

15th June 2022 | Words by Matt Jones


Fashion is a fickle thing. But there’s one look for men that has never gone out of style – and that’s the rugged outdoorsman look. There’s a good reason for that: it’s timeless, gritty and unapologetically masculine, but not one that shouts too loud or tries too hard. It’s honest and authentic, channelling a spirit of adventure, of hard work and a life well-lived.

Of course, looking ‘rugged’ is about far more than wearing the right clothes – but it certainly helps. Because we’re firm believers than having a practical and hard-wearing wardrobe that is designed for life outdoors can actually inspire you to be more adventurous, to test yourself and push your limits.

It also represents a more sustainable approach to buying clothes. That’s because the true outdoorsman values high-quality items that are fit for purpose. They’re clothes that are designed for the long haul – to be used and abused, but also cherished and cared for. Gradually, you’ll build a select wardrobe of heirloom pieces that one day, you might pass down to the next generation. And you won’t grow out of them either, since the rugged outdoorsman look can suit a man of any age, young or old. It only gets better with time.

But what exactly is rugged style? Typically, it draws its influences from traditional blue-collar workwear made for farm, forest and factory, or military-issue kit built for battlefield and barracks. Clothing originally designed for shooting, hunting and field sports also works well, as do heritage pieces inspired by the heroes of yesteryear – think mountaineers, explorers and sailors.

Good examples include leather work boots and heritage denim or canvas pants, topped off with flannel shirts, heavy knit pullovers and wool coats. Military-derived field jackets or parkas also work well for outerwear. Of course, there are no rules, and style is all about the individual, so many other pieces of clothing can fit into an outdoorsman’s wardrobe too, provided they’re functional, versatile and durable.

In essence, we reckon there are three basic qualities that define the look and feel of a true outdoorsman’s wardrobe:

Built to last

Quality is the hallmark of classic outdoor style. The outdoorsman does not follow trends or fads and does not care about ‘fast fashion’: his style is timeless and his clothes have character. In fact, this usually means that the older a garment is, the better it gets – the aim is to wear your clothes in, not wear them out. Embrace the concept of wear and tear. This is an advantage of wearing heritage fabrics, since most can be easily patched and repaired when needed, or even rewaxed and reproofed to restore performance. Remember, every stitch tells a story.

Ready for action

What you wear should allow freedom of movement, without being restrictive. Basically, the cut of your clothes should mean you can easily swing an axe, shoulder a gun or cast a fishing rod. But that doesn’t mean baggy and shapeless – clothing should permit dynamic movement, without looking sack-like. It’s about liberation and freedom, not buttoned-down stuffiness.

Designed to take on the elements

Your clothing should be fit for purpose – its purpose being to protect your body from the harsh elements. Typically, this means selecting fabrics that are hardwearing and weatherproof, as well as temperature regulating – the idea being that they’ll keep you warm in cold, windy and exposed conditions, and cool in hot and humid environments. It’s about being protected from cold, wind, rain, sleet, snow, hail and occasionally the baking heat of the sun, whilst remaining cool, calm and collected.

Crafting an outdoor-ready outfit

Follow those guiding principles above and you should be able to craft your own rugged style and put together an outdoorsy wardrobe. But if you need a few more specific ideas on where to begin and what to wear, we’ve also broken it down for you below, piece by piece...

Baselayers

Layering is the key to comfort in the great outdoors, and it begins with your baselayer. For athletic pursuits, you can’t go wrong with merino wool – it’s nature’s own miracle fibre, being soft, warm, breathable, moisture-wicking and naturally anti-bacterial to stave off body odour. But for everyday wear, we’re big fans of a classic Henley top. Originally designed for muscular rowers, these button-placket tops come in short and long-sleeved variants, making them the perfect layering option under a heavier shirt or pullover.

Underwear

Don’t scrimp on what you wear down there. If you’re most comfortable in briefs or trunks, go for it – though personally we’re fans of SAXX underwear, which feature the fabulously-named patented BallPark Pouch. For comfort, support and zero risk of chafing, even on extended hikes, they’re the best boxers we’ve found.

Rugged Shirts

The quintessential outdoorsman style staple has to be the flannel shirt, ideally in a heavyweight or midweight cotton. Rugged and hardwearing, they’re the perfect do-anything, go anywhere wardrobe choice. The iconic look is a hunting-inspired buffalo check or a classic plaid – think Filson’s Alaskan Guide Shirt or British brand &SONS’ own take on this classic, their handsome Yukon shirt.

In the shoulder (and colder) seasons, you can wear multiple layers under a flannel shirt to add warmth, or you could switch to an even heavier wool overshirt. Another alternative is a quilted or insulated lined shirt, sometimes called a ‘shacket’ by fashionistas.

Knitwear

Spending time in the wilderness, exposed to the elements, means the rugged outdoorsman needs serious warmth. The go-to options are heavy wool pullovers, as worn by Shackleton and other early polar explorers, or navy-inspired submariner sweaters. A traditional fisherman’s ‘gansey’ or ‘guernsey’ does much the same job, but look for high-quality wool in chunky, heritage patterns and traditional muted colours. Then there are sweaters and cardigans – again, pick simple block colours with chunky buttons and other simple details.

Vest and gilets

A further useful addition to a cold-weather wardrobe is to ‘invest’ (ahem) in a warm vest, gilet or bodywarmer – like Amundsen’s Groomer Gilet or Filson’s Tin Cloth Work Vest. Boosting your core warmth without impairing arm and shoulder mobility or adding too much bulk, a vest makes for practical and versatile winter wear. Look for rugged details like contrast shoulder yokes in tough fabrics for authentic 1970s Canadian logger vibes.   

Outerwear

Your final line of defence from the cold, wind and rain should be a sturdy coat or jacket. Obviously, your choices here can change with the seasons, but practical features like warm and weatherproof fabrics, snug-fitting collars, storm flaps, cinchable cuffs and plenty of pockets are all factors to consider. As always, durability and functionality are key.

If you need to button up against the cold, a long-length parka or a wool cruiser like Filson’s iconic Mackinaw is a great choice. If you want hard-wearing utility, you can’t go wrong with a good field jacket. And if you need more technical waterproof performance, try one of cult climbing brand Klattermusen’s stylish shells, or perhaps some outerwear from Japanese brand Snow Peak’s FR range – made from fire-resistant fibres that are campfire-ready.

Pants and trousers

Trousers can be tricky to get right. But in essence, the outdoorsman needs sturdy and straightforward strides – heritage and workwear-inspired kecks are often the way to go, in muted or darker tones that will hide dirt, grease and grime.

Heavyweight denim is always a winner, especially in selvedge indigo, which channels a bit of Wild One-era Brando in all the right ways. Or you could go for khakis or chinos – flat fronted, with no crease. We’re big fans of DUER’s Live Free Adventure Pants and No Sweat Pants, which both use their unique stretch fabric for unparalleled comfort.

EDC accessories

The rugged outdoorsman is a practical sort of chap, and that means your everyday carry should include some sort of utility tool. This might range from a keyring bottle opener to a small pocketknife, such as those from Portland knifemaker The James Brand. If you’re venturing further off the beaten track, you might want to add a field repair or firelighting kit from survival brand Exotac.  

 

Backpack

Whether you’re going grocery shopping or foraging in the forest, a solid rucksack is an everyday carry essential. A small daypack of around 20 litres is ideal for adventures essentials like food, water and spare layers, but will also do double duty in the city when you are carrying the concessions to modern life that we all need – like your smartphone, tablet or laptop, plus keys and wallet.

Osprey’s heritage-inspired Archeon series of packs are our current favourites, closely followed by Mystery Ranch’s Urban Assault packs (developed from a design originally conceived for the US military). 

Eyewear

Squinting in the sun ain’t no fun, and a trusty pair of sunglasses is a functional bit of outdoor kit, not just a fashion accessory. Look for full UV protection, robust and comfortable frames, and polarised lenses for optimum optical clarity, contrast and definition. Pick frames that suit your face – oversized aviators are great for chiselled, square jawed types, while classic wayfarers look good on almost anybody. Check out Sunski’s extensive range to find your perfect pair. 

Wristwear

The discerning outdoorsman does not wear a smartwatch. Wilderness adventures call for a reliable timepiece. So, far better to go for a traditional wristwatch, with either a rugged quartz or shock-protected mechanical movement. The classic choice would be a field watch, but if you spend a lot of time in or on the water, there’s a case to be made for a vintage-style dive watch too. Our brand of choice? Elliot Brown, of course. If they’re good enough for British special forces, mountain rescue teams and the RNLI, they’re good enough for us.

Headwear

Cold weather headgear typically entails a classic watch cap – a ribbed knitted beanie originally worn by seamen on watch, hence the name. For sunnier climes, a trucker or logger cap is ideal – but look for a hat with a good quality rear strap and bill, ideally made from a tough fabric that’ll wear in nicely, even if it gets a little sun-bleached or salt-stained. Our go-to options are Filson’s Mesh Loggers or Low-Profile Oil Tin Cloth Caps.

Footwear

A good pair of boots will probably outlast your knees, making them the only proper choice for a discerning outdoorsman. For ultimate durability, iconic US work boots like the Wolverine 1000-Mile or Red Wing Iron Ranger are the way to go. Alternatively, if you want a ‘heritage hiker’, check out brands like Danner or Ridgemont – we’re also big fans of Fracap’s mountain-inspired Scarponcino boots. 


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