We like to think of ourselves as wise investors in fashion rather than wasteful big spenders, but one of the good things about cold weather is that it gives you an excuse to reach a little further into your pockets than you normally would. Which is another way of saying: the best winter jackets tick a lot of boxes, so let me at that shearling.

Bought well, a winter jacket is impactful, head-turning outerwear, not just a boring, sensible purchase. Some of the most wearable styles are bona fide menswear hall of famers, sported by wartime heroes and Hollywood royalty alike. There are a few smarter options on our list, but most of our favourites were built for purpose – rugged, practical layers whose durability in style is down to their durability of design.

From workwear classics to reappraised retro designs, these are the winter jackets you should be feeling warm about this season.

Lined Trucker Jacket

If there’s one winter jacket which can’t be accused of style over substance, it’s the lined trucker jacket. Yes, it’ll bestow lashings of rugged, outdoorsy vibes on even the most committed couch potato, but it’s got the stellar insulation and reliable hardiness to back up its rep. The regular denim jacket is surprisingly long in the tooth (the first iteration was served up in the 1880s) so the trucker jacket’s 1960s birthday makes it a baby in comparison.

Working much on the same premise as its forefather – but with the added benefit of a more streamlined shape – the trucker jacket trims back on fat. It’s all useful pockets and comes crafted from a variety of fabrics that can withstand a fair bit of rough and tumble. The big win you’ll get from a trucker jacket though is its timeless brand of style and when you take into consideration its lining (borg or otherwise) its deservingness to be in your winter jacket line-up is frankly indisputable.

Pro Styling Tip

The outer fabric of trucker jacket is is often stiff, so when you’ve got a lining chucked into the mix too you’ll need to avoid chunky knitwear and try something finer such as merino or cashmere instead.

Mango ManMango Man

The best lined trucker jackets

Mason Wool Blend Trucker Jacket - Click to buyLEVI'S Sherpa Jacket - Click to buyWrangler TRUCKER, Light jacket - Click to buyVolcom KEATON, Denim jacket - Click to buy

Shearling Flight Jacket

Arguably the statement jacket of the past couple of years, the classic flight jacket in shearling (or at least something that looks like it) combines flyboy drama with extra-sensible winter insulation. Modern versions faithfully replicate the styling of the RAF’s Irvin Flying Jacket, first produced in the 1930s, or the G1 worn by US Navy and Marines during World War II. Look for a belted waist, adjustable cuffs and a sheepskin collar with all the subtlety of a Boeing Flying Fortress.

It may be designed for altitude, but even on the ground this is a garment of high style. They look the business with most trousers made of wool, cotton or denim, but for our money, tonal outfits work best. Select a jacket in black or navy and go dark with your trousers and T-shirt. Or use the accent colour of the collar and lining and replicate it your jeans or knitwear.

Pro Styling Tip

Flight jackets are often cut boxy because they were originally designed to wear over chunk knits in bitterly cold cockpits. Today, you might not need all that padding so try a size down before taking off for the checkout.

Brunello CucinelliBrunello Cucinelli

The best shearling flight jackets

SELECTED HOMME Navy Zip Up Check Borg Collar Jacket - Click to buyBurgundy borg collar jacket - Click to buySheepskin Collar Bomber Leather Black - Click to buyMR P. Shearling-Trimmed Checked Wool-Blend Aviator Jacket - Click to buy

Raincoat

You need a raincoat for winter. Obvious? Yes it is, rather, but men in bizarrely persistent numbers still brave wet weather in winter coats that soak up water, rather than repel it. We’re not saying the solution is a £900 mac here, but lightweight, practical outwear that folds up small and looks as good with tailoring as it does with denim.

Pro Styling Tip

Raincoats boast one of the widest spectrums of colours in all of menswear, so use it to break the monopoly of greys and navy in your outerwear. Primary colours like red and yellow work but for something slightly less attention grabbing, try pastel greens, pinks or blues.

ZaraZara

The best raincoats for men

Patagonia Men's Torrentshell Pullover - Click to buyNASLUND TRICLIMATE® JACKET - Click to buyTRETORN Rain Wings Jacket - Click to buySTONE ISLAND MICRO REPS HOODED ZIP JACKET - Click to buy

Worker Jacket

The chore, or worker jacket, may be the ultimate layering piece come winter. Big claim, but it works as an ideal middle layer, offering up increased functionality underneath a heavier overcoat with its multitude of pockets. This level of usability is of course how the jacket came to be – it was originally utilised by factory workers in nineteenth century France, and rather than mobile phones and wallets, its pockets were needed for tools to help with the worker’s duties.

The basic style hasn’t changed at all since that time. Typically they’ll come in boxy fits and with three or four patch pockets and one or two interior pockets. While they used to be exclusively made from hard wearing cotton twill or moleskin, today you can find them in anything from soft wool mixes to waterproof nylon, meaning it’s easy to find a style to suit your exact needs, factory worker or not.

Pro Styling Tip

On a cold day, skip knitwear and just button up a heavyweight chore jacket underneath an overcoat. You’ll get the same warmth as you would from a jumper, but with the added bonus of boss-level layering. And a few extra pockets.

Mango ManMango Man

The best worker jackets for men

vetra twill no.4 workwear jacket - Click to buyCarhartt Men's Duck Chore Coat Blanket Lined C001 - Click to buyARPENTEUR QUART LINED JACKET - Click to buyUniversal Works Merino Check Bakers Chore Jacket - Click to buy

Wool Jacket

This is the broadest category on our list because most jacket styles are available in wool in one kind or another. The one we’re particularly interested in right now, however, is a cropped, workwear-style jacket that brings a touch of the outdoors to the city. Think brushed wool, expansive pockets, perhaps a borg or fleece lining – rugged Americana that Springsteen could write a song about.

Better for cold days than wet ones, run with the blue-collar associations for casual outfits with tough selvedge denim and work boots.

Pro Styling Tip

Get more wear from this type of jacket by not just thinking of it as a casual piece. Clash your style tribes by layering one over a preppy combination of tailored trousers, sweatshirt and cotton button-down shirt for a modern take on business-casual.

FarahFarah

The best wool jackets for men

Fleece Lined Blanket Coat in Dark Red - Click to buyZip-up Overshirt Wool Teddy - Click to buyJOHN LEWIS & Co. Moons British Wool Check Lumber Jacket, Blue - Click to buyHOUNDSTOOTH BOMBER JACKET - Click to buy

Fleece Jacket

After hiking shoes and all manner of technical gear came down from the mountains and went fashion, it was only a matter of time before designers coaxed us to wear fleece. As it turns out, not a hard sell. Fleece jackets are wearable blankets, after all, and the latest versions enjoy the same mix of flattering cuts and nerdy nostalgia as corduroy has been in recent years.

If you’re sheepish about animal skins, know that fleece is a man-made material (sometimes made of recycled plastic but not always). The fabric is so popular right now that you’ll find a range of types, from oversized overshirts to classic zip-up hoodie styles. Greens, navy and black will all play to the great outdoors vibe, but in our opinion you can’t beat classic creams and mocha shades in this shag-pile sherpa.

Pro Styling Tip

Don’t want to follow the herd? Play against type by pairing a fleece jacket with some cropped pinstripe trousers or white jeans and high-top sneakers for a solid streetwear outfit.

BershkaBershka

The best fleece jackets for men

Sweatshirt Taibe - Click to buyMen's sherpa fabric zip-up cosy fleece - Click to buyMEN FLUFFY YARN FLEECE ZIPPED JACKET - Click to buyCHIMALA Fleece Jacket - Click to buy

Quilted Bomber Jacket

When you think of cold weather jackets, a bomber probably isn’t the first thing that comes to mind. Sure, most are water and wind-resistant thanks to their durable nylon shell and ribbed trims (a result of being designed to keep fighter pilots warm without the bulk of a flight jacket), but lightweight spring-ready styles are unlikely to withstand blood-thinning temperatures.

To be protected even in extreme conditions, make a quilted bomber jacket — also known as an MA-1 in military jargon — your first layer of defence. Premium takes lined with down or affordable options that use synthetic feather fill act almost like a cropped puffer jacket, providing optimum insulation from the waist up.

Pro Styling Tip

Along with a suit, outerwear is often one of the biggest budget-busting expenditures in a man’s wardrobe. With that in mind, it makes sense to get the most return from your investment. Several high-end and high street brands turn out quilted bombers that can be well, turned out; reversible jackets that offer two for the price of one and send your style stock sky-high.

Selected HommeSelected Homme

The best quilted bomber jackets

ALPHA INDUSTRIES MA-1 PUFFER JACKET - Click to buyMONCLER GILLEY - Click to buyPUFFER JACKET - Click to buyQUILTED BOMBER JACKET - Click to buy

Field Jacket

In spring and autumn, a cotton or linen field jacket offers a sound way to layer up without burning up. In the depths of winter, however, you need something more substantial. Look for the multi-pocketed design in waxed cotton, leather, wool or quilted versions and it will be an ever-suave outer layer that can stay in your wardrobe for years.

This is another cool jacket with a decorated military background, the design first created for the battlefield – but its heritage also includes countryside pursuits and motorcycles (confusingly, some brands will refer to theirs as motorcycle jackets). Whatever your vibe, play on the heritage with raw denim or wool trousers and the best boots you own.

Pro Styling Tip

To turn up the heat of your outfit both literally and sartorially, wear your field jacket over a roll neck. Then put your hands in your pockets, casually raise an eyebrow and street style photographers will sense your presence from 10 miles away.

BelstaffBelstaff

The best field jackets for men

J.CREW Cotton Field Jacket - Click to buyB.INTL DUKE WAX JACKET - Click to buyDiamond Quilted Thermoregulated Field Jacket - Click to buyPhotographer's Jacket Banbury Charcoal - Click to buy

Down Jacket

No piece of menswear is as hotly debated as the down jacket. Well, maybe socks and sandals but the reasons for that one are somewhat different. Down feathers are found underneath the harder exterior feathers on a bird. They’re the best thermal insulator you can get, used in all manner of products from jackets to sleeping bags.

Animal welfare groups are mainly concerned at the plucking of these down feathers from live birds and although this practice is illegal in the US and UK, it isn’t outlawed in China, where 80 percent of the world’s down is produced. If you have concerns, do your research on the brand before you buy.

These are highly technical pieces better suited to serious sub-zero treks than outside in the pub garden on a Friday in January. Anything at 600 and above will do the job admirably. At its current state down is still a better thermal insulator than any synthetically made alternatives (although the tech is catching up).

Pro Styling Tip

Do not go wide legged. Down jackets always work best with slim jeans to counteract the jackets puffy volume. If you’re worried about looking blown up like a Michelin man blimp, look for a down jacket in a slimmer cut or a padded jacket that’s cut closer to the body. These jackets can also be used effectively as a second layer under an oversized coat.

Canada GooseCanada Goose

The best down jackets

CANADA GOOSE Lodge Packable Shell Hooded Down Jacket - Click to buyPOLO RALPH LAUREN Packable Quilted Down Jacket - Click to buyBARBOUR LIDDESDALE® QUILTED JACKET  - Click to buydown & feather jacket with stormwear - Click to buy