Whether you’re facing rain, hail, or wind, finding winter clothing that’s comfortable, practical, and stylish can feel like an empty-centred Venn diagram.
Building a winter wardrobe means investing in pieces that’ll last until next winter, and the next, and the next, etc. Therefore, the key to winter clothing that’ll last relies on a few core tenets:
- Quality over quantity.
- Style over trend.
- Versatility over specificity.
And like all good rules, these are made to be broken – more on that momentarily. Here’s how to dress this (and every) winter.
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The Go-Anywhere Jacket
‘Winter’ and ‘outerwear’ are synonymous. Gone are the days of donning a Kathmandu puffer and calling it a day – and whilst there’s no shame in the black ode to the Michelin Man, there are far more flattering ways to stay warm.
We love the proportions of the military-style flight jacket from Braindead, or the sleeker leather jacket from legacy brand Golden Bear. More versatile picks like this denim jacket won’t get any hanger time, and for bad-weather days, invest in a black rain jacket that won’t make you look like a Hunger Games tribute.
Flock To Knitwear
Knits are an easy way to look like you’ve made an effort without actually trying.
The R.M.Williams cream quarter zip is thick enough to wear alone, with a wide lapel to cast off any finance bro aspersions. Win a game of chess in this Venroy lambswool jumper, or this lighter Acne Studios knit.
If you’re a chronic overheater like I am, then a cardigan like this one from Our Legacy is awesome for temp regulation.
Shirt Notice
A lightweight button-up is key to successful layering in winter, and this UNIQLO shirt (which we styled back in Feb) remains a winner: affordable, crisp, uncreaseable, and versatile.
Something dressier like this mfpen pinstripe has your date night sorted, and a thicker corduroy shirt like this Tommy classic adds texture without screaming for attention. Grey Mondays will also be vastly improved with this Husbands shirt‘s 70s-inspired collar and cuffs.
Tee Time, All The Time
For more casual occasions, there’s nothing as indispensable as the humble tee. Our current faves do everything a good tee should: breathable, a Goldilocks fit, and versatile.
This Rag & Bone henley is one such example – it comes in a variety of colours, it’s breathable, and its detailing (like metal buttons and longer cuffs) sets it apart. The viral The Bear t-shirt is another one that’ll serve you well (though it mightn’t improve your julienn-ing), and the boxier Lemaire longsleeve offers a heavier, more architectural option.
For ultimate dependability, get this three-pack from Cos.
Below The Belt
So you’ve got a pair of 501s. What now?
Lean further into the vintage feel with these engineer-fit RRL pants, or come back to the present in these Nudie jeans. Both offer a great fit, durability, and will work well on most outfits.
The Dries Van Noten Paxford pants offer a tongue-in-cheek take on a traditional military pant, but when in doubt – an unassuming (but well-made) pair of chinos will do all the work.
Sole Providers
Your shoes say a lot. Mostly: do I own a mirror? The right winter footwear should be cosy but not clunky.
Strap on some Paraboots to meander through meetings, markets, and manageable mountain paths. If your R.M.s are holding down the Chelsea boot fort, then outclass them with a pair of Saint Laurent Wyatts. Think of it as a one-time payment on an instant outfit improver.
One trend worth following is a pair of sleek, colourful sneakers, and anything that requires breaking a sweat can be confidently handled by a pair of Salomons.
Chez Devil
You’ve sorted your top and bottom halves – well done. But the difference between “guy who owns clothes” and “guy who knows how to dress” is all in the details.
Most guys want a formula – “this jacket with those shoes” – but the truth is, there are heaps of ways to do it right. Wear sneakers with a suit. Throw a tie on with jeans. Slip on a dress watch with a band tee. The trick isn’t to follow rules: it’s to learn the ratios between your clothes.
Once you get the hang of texture, silhouette, and proportion, you’ll stop Googling “cool men’s winter outfit” with your Saturday coffee.
So finish it off properly. A clean woven leather belt, a soft lambswool scarf and a pair of Wayfarer-style sunnies all add visual interest, making you the most put-together man on your end of the train carriage. Finish it off with an understated signet ring and you’re golden.
Still looking to elevate your winter style? Add a spritz of our top winter fragrance picks, or suit yourself with something bespoke to go with your winter clothing.
