The five menswear rules of winter dressing
The Times
Peter Bevan
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The five menswear rules of winter dressing
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From layering to well-placed pops of colour, here's how to make the coldest months your best-dressed yet with Mr Porter's Winter Shop
An investment coat will see you through this winter and beyond
mr porter
Peter Bevan
Monday October 19 2026, 4.00am
BST
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The Times
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I'll say it: winter is the best season to get dressed. Your commute may start to feel like an Arctic expedition in the pitch black, but the flip side is that you can have far more fun with what you wear. There's plenty to play with: layers, fabrics, textures. It's the season for the heft of a proper wool coat or a crisp collar peeking out above soft cashmere — and there are more ways to get it right (or, let's be honest, wrong).
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So, here's how to do it. Below you'll find five rules. Some are tried and tested; others take their cue from this season's catwalks. All have staying power beyond the trend cycle, whether it's layering that looks deliberate or well-placed pops of colour to break up all the grey. Everything here comes from
Mr Porter's Winter Shop
, home to staples you'll wear every year alongside directional pieces from labels you've yet to discover.
1. Layer with intent
It's cold, so you're going to be wearing layers. The difference between looking bundled up and put together, though, is intention. Two shirts worn together, a rollneck under a white button-up, a T-shirt beneath a V-neck or a cardigan under a coat. The key? Each layer should be seen — a collar here, a hem there, a cuff peeking out from a sleeve. That's what builds texture and interest, even if you're wearing all black.
Graphpaper cotton-poplin shirt
£280,
Graphpaper at Mr Porter
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Mr P. Clyde cashmere rollneck sweater
£345,
Mr P. at Mr Porter
Lemaire double-breasted wool and alpaca-blend felt coat
£1,495,
Lemaire at Mr Porter
Our Legacy Third Cut straight-leg jeans
£330,
Our Legacy at Mr Porter
2. Brighten the grey
Once you've got layering down, introduce some colour. Winter wardrobes tend to drift towards navy, charcoal and black, so even a small hit of something bright goes a long way. Plenty of this season's catwalks agreed: Japanese label Ssstein showed how effective a single shot of colour can be across knitwear, shirting and outerwear, while Jil Sander took the simplest route of all — bright socks. Either way, the trick is placement, not quantity. A cobalt knit thrown over a dark coat, a flash of green beneath a V-neck, or a bright shirt under a beige jacket. Aim for surprise, not statement.
Auralee striped wool-jersey T-shirt
£280,
Auralee at Mr Porter
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Loewe anagram-embroidered cotton shirt
£675,
Loewe at Mr Porter
Paul Smith cashmere sweater
£495,
Paul Smith at Mr Porter
Mr P. brushed-cashmere sweater
£395,
Mr P. at Mr Porter
Bode logo-appliquéd cotton-jersey T-shirt
£270,
Bode at Mr Porter
3. Feel the difference
From denim to wool to cashmere, this is the time of year when your choice of fabric really counts. Heavy, natural textiles keep you warmer, wear better and look richer than anything lightweight or synthetic. They usually age well, too — a pair of dense indigo jeans or a proper wool coat, for instance, only get better every winter. So it's no coincidence some of the most coveted labels right now are fabric obsessed: Auralee, for example, is a Tokyo brand that develops many of its own yarns directly with Japanese mills. When in doubt, go heavier.
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Agolde Grover wide-leg jeans
£300,
Agolde at Mr Porter
Mfpen Conference double-breasted wool coat
£895,
Mfpen at Mr Porter
A.P.C. Malaury checked wool-blend flannel shirt
£295,
A.P.C. at Mr Porter
Ralph Lauren Purple Label cashmere cable-knit sweater
£1,050,
Ralph Lauren
at Mr Porter
4. Dress up, not stiff
You don't need a whole new wardrobe for party season, just a few well-chosen pieces. The aim is to look like you've made an effort without the “I've got my fancy shirt on” energy. Say it with silhouette over shine: a big collar, a sharp lapel or a strong cuff will do far more than garish colour or embellishment. Call it the Bryan Ferry method: relaxed tailoring, one interesting detail, and nothing that feels overdone.
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Mr P. wool, silk and cotton-blend blouson jacket
£845,
Mr P. at Mr Porter
Toteme striped cotton-poplin shirt
£400,
Toteme at Mr Porter
Boglioli double-breasted virgin wool-hopsack blazer
£985,
Boglioli at Mr Porter
Jacquemus Tempo wide-leg woven wool-blend trousers
£650,
Jacquemus at Mr Porter
Sebago Daxton leather loafers
£295,
Sebago at Mr Porter
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5. The finishing touches
Accessories do the heavy lifting in winter. A belt breaks up an outfit beneath an open coat, while a cap is the smart answer to drizzle: look for waxed cotton or, in Loro Piana's case, a water-repellent finish. Leather shoes or boots with proper grip are non-negotiable. Then there's the scarf. Take your cue from Richard E Grant in
The Celebrity Traitors
, whose theatrical scarves (by Burberry, no less) became a national talking point — mostly because he never seemed to take them off. The lesson? Wear yours with conviction, even indoors.
Brunello Cucinelli suede hiking boots
£1,400,
Brunello Cucinelli at Mr Porter
Loro Piana logo-embroidered Storm System baby cashmere baseball cap
£470,
Loro Piana at Mr Porter
Toteme 2.5cm leather belt
£320,
Toteme at Mr Porter
Anderson & Sheppard frayed checked cashmere-twill scarf
£485,
Anderson & Sheppard at Mr Porter
Grenson Milo leather Chelsea boots
£520,
Grenson at Mr Porter
Read more luxury reviews, advice and insights from our experts
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