



Blue puffer jacket, polo & navy trousers
£273*For cold days, about −5 to 5°C · Outdoors · 4 pieces from £27*
Warm winter outfits for men, built on an overcoat, parka or puffer, a heavy knit or flannel, dark denim or wool trousers, and boots. 1,124 complete looks, each with why it works.
By Ivan Kachur · Updated October 2026 · How to dress for winter
In winter I'd spend on the coat and the boots and keep everything under them simple: a heavy knit or a flannel, dark jeans or wool trousers, in colours that sit together. Then the coat can go on and off and the outfit still holds up indoors.
Ivan Kachur, Wholefit
Think in three layers. Next to the skin, something that holds warmth in: a merino or thermal top, or a fine knit. In the middle, the layer that insulates: a jumper, a cardigan, a fleece or a flannel. On the outside, a coat that stops wind and wet: a wool coat for dry cold, a puffer or a parka once it's below freezing (0°C) or raining. Your legs and feet matter as much as the coat: full-length trousers or jeans, warm socks and closed boots.
Put the thinnest layer underneath and the thickest on top, and keep each one close enough to the body that the next slides over it. A fine merino or roll neck under a chunky knit looks neater than two chunky knits. Choose a coat with room in the shoulders rather than one that strains over a jumper. Keeping the layers to one or two colours, like cream and camel or navy and grey, makes them read as one outfit rather than a stack of pieces.
Swap one piece at a time. An overcoat or a wool chore coat instead of the puffer on days that are cold but dry; wool trousers or corduroys instead of jeans; a roll neck or a shawl-collar cardigan instead of a hoodie. Leather boots with a lug sole do most of the work: they handle slush and look right with denim and trousers alike.
Look for a rubber lug sole with real tread and leather or suede treated against water. Smooth leather cleans up best after salt: wipe it with a damp cloth and let it dry away from the radiator. Keep suede and canvas trainers for dry days. If you walk a lot in snow, a lined, waterproof boot half a size up leaves room for thicker socks.
Deep neutrals are the easiest base: camel, chocolate brown, charcoal, navy and cream. Add one richer colour, like burgundy, forest green or rust, through a knit or a scarf. Black works too, but mixing textures (wool, leather, cord) keeps an all-black outfit from looking flat.
For dry days around freezing, yes, with a knit underneath: look for 70% wool or more. Below about -7°C, or in wind and rain, a down puffer or a hooded parka is warmer for its weight.
On dry days, yes: leather or suede trainers with a thicker sole look right with jeans and a coat. On wet or snowy days, switch to boots; canvas and mesh soak through and salt marks them.
Three is usually enough: a tee or base layer, a knit or flannel, and a coat. On very cold days, add a thermal under the tee rather than a fourth bulky layer, so the coat still fits.
1,124 looks
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For cold days, about −5 to 5°C · Smart casual · 4 pieces from £95*
For cold days, about −5 to 5°C · Outdoors · 4 pieces from £155*
For cold days, about −5 to 5°C · Work · 4 pieces from £110*
For cold days, about −5 to 5°C · Outdoors · 4 pieces from £70*
For cold days, about −5 to 5°C · Outdoors · 4 pieces from £70*
For cold days, about −5 to 5°C · Work · 4 pieces from £41*
For cold days, about −5 to 5°C · Work · 4 pieces from £135*
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For cold days, about −5 to 5°C · Work · 4 pieces from £90*
For cold days, about −5 to 5°C · Everyday · 4 pieces from £95*
Counted from 30 of these looks.
Brown, black, cream and denim come up most often across these looks, so they make an easy base to build on.
Most whole outfits here cost between £334 and £733; the typical one is £591. Swap any piece to change the total.
Most pieces come from ALDO, Wax London, Weekend Offender, Folk and Tommy Hilfiger. Each look checks out on the stores' own sites, one store at a time.