What to Wear When Walking in the Cold: A Complete Kit, Six Pieces at a Time

Sep 20, 2026
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Following on from Luke Christiansen’s The right hiking shoes after 60: why comfort, fit and the individual matter more than the brand, I decided the shoes were only half the job done. A great pair of walking shoes matched with the wrong clothing is still a cold, miserable walk, just one with excellent footing. So I put together, and properly tested, a full cold-weather walking kit, six pieces in total, and reviewed each one with the same honesty I’d want if I were the one reading it.

Fjällräven Singi Heavy Flannel Shirt, $274.95

This is not flannel as the Australian imagination understands it, some flimsy thing worn ironically to a barbecue, but proper heavy organic cotton, the kind with actual mass, actual structure, reinforced at the collar and cuffs with Fjällräven’s own G-1000 fabric so it survives you rather than the other way around. It kept me warm, looked appropriately serious, and made me feel, briefly, like a man who chops his own wood. I don’t. But I could have.

Icebreaker Merino Hike+ Medium Crew Socks, $44.99

A sock, I’ll admit, is not a garment I’ve historically had strong feelings about. These changed that, somewhat against my will. The cushioning sits exactly where a foot actually needs cushioning, rather than everywhere in a general, unhelpful sort of way, and the anatomical shaping means the left sock knows it’s a left sock, which fewer socks manage than you’d think. My feet stayed dry, warm and entirely uncomplaining across a proper cold-weather walk, and I’ve since learned that a good pair of socks is not, in fact, a boring purchase. It’s simply an unglamorous one, which is a different thing entirely.

Fjällräven Sten Fleece, $199.95

Made from recycled polyester, which sounds virtuous and also, mercifully, does not feel like wearing a converted plastic bottle, this fleece did the quiet, unglamorous work a good midlayer is supposed to do: kept the cold out, took up almost no room in the bag, and never once drew attention to itself. The high collar earns its keep against a proper wind. Nothing dramatic to report, which, in outerwear, is precisely the highest compliment I know how to pay.

Macpac Merino 150 Beanie, $49.99

A beanie’s entire job is to sit on your head and not make you look ridiculous while doing it, and this one manages both with more grace than I expected from a single piece of fine merino. It’s snug without leaving a mark, warm without any of the itch I’ve come to associate with lesser wool, and entirely unremarkable in the way a good beanie should be, meaning nobody at any point asked me a single question about my hat. That is precisely the level of attention a hat should attract. The fold-up cuff is a small, sensible touch too, giving you a bit of adjustable coverage over the ears when the wind decides to be unreasonable.

Sealskinz Merino Liner Gloves,  $55-60

I was initially unconvinced by the concept of a glove thin enough to still operate a phone, having previously understood gloves and phones to exist in a state of permanent, irreconcilable conflict. These resolved the conflict rather neatly. Thin enough for genuine dexterity, warm enough that I forgot I was wearing them until I took them off and immediately regretted it, and merino enough that they didn’t develop the particular, faintly upsetting smell some synthetic liners acquire by lunchtime. They’re designed to slip under a heavier waterproof glove too, if the weather turns properly hostile, which feels like exactly the sort of forward planning a glove ought to be doing on your behalf. A small, unglamorous hero of the whole kit.

Icebreaker Merino 200 Oasis Long Sleeve Crew Thermal Top, $149.99

I approached this with the deep, weary suspicion of a man who has owned a great many thermals that promised much and delivered a faint, apologetic warmth somewhere around the collarbone. This one is different. It’s proper 100% merino, not a merino-adjacent blend doing its best impression, and it does the thing merino is supposed to do but so rarely actually does: it kept me warm without making me feel like I was wearing a small, insistent radiator. I wore it two days running without incident, which for a garment sitting directly against skin is a genuinely significant endorsement, not a lapse in hygiene.

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