Here’s how to make your biggest wardrobe investment of the season a smart one.

It’s customary at this time of year for us to present you not only with a breakdown of the coming season’s trends, but a suggestion of which type of coat we think you ought to invest in and why. Having pored over this season’s new outerwear selection, though, we must admit that we’re struggling to come to a consensus. There is simply too much choice out there for us to consider settling on a single style, which is why this year we’ve chosen to highlight five different categories instead.

From classic Crombie and Chesterfield overcoats to hard-wearing parkas, down jackets and shearling jackets – which, by the way, look set to be just as popular with the style cognoscenti this year as they were the last – there should be something here to suit every man and every climate. We took a few of our favourites, from designers such as Tom Ford, Haider Ackermann, Moncler and Belstaff, up to the wilds of the Scottish Highlands to put them through their paces.

After a decade or two spent languishing in fashion purgatory, shearling was thrust well and truly back into the spotlight last year when brands such as Coach and Burberry made sheepskin a highlight of their AW collections. But this was no passing fad, and late adopters have no reason to be sheepish: the current season’s crop of coats and jackets is, if anything, even better than the last, with high-end brands such as Loewe and Loro Piana injecting a dose of luxury into this rugged, hard-wearing classic.

Urban life during winter typically involves moving from heated lobby to sub-zero street and back again at a moment’s notice. A flexible approach to dressing for the elements is therefore required, and there’s no better or more stylish solution than the down jacket. This season’s best, from brands such as Moncler and Arc’teryx Veilance, provide excellent insulation without weighing you down, and look great to boot.

When shopping for a winter coat, it’s only natural to look for something that’s able to withstand the elements. Realistically, though, unless you live in the Arctic Circle, you’re not going to be encountering sub-zero temperatures and driving snow on a daily basis. There’s likely to be a lot of pesky in-between weather to deal with, too: not warm enough for a proper overcoat, but too cold for no coat at all. Navigating those tricky transitional months in style means investing in an unstructured coat made from a lighter material, such as this suede field jacket from Loro Piana.

While the classic leather and shearling bomber jacket was designed to keep WWI fighter pilots warm in exposed cockpits at low altitudes, the heavily padded MA-1 was intended for the jet age. The jacket’s exaggerated proportions have made it a favourite with fashion designers, many of whom – Rick Owens being the name that springs most immediately to mind – revisiting the design on a more or less annual basis. This season, look to versions from Beams Plus, Casely-Hayford and Jil Sander, pictured.

Often described as the first coat that a man should buy, the classic overcoat remains as savvy an investment as ever. This season’s version is a particularly ankle-sweeping, romantic take on the piece, calling to mind military greatcoats of the first half of the 20th century, and characters such as Heathcliff from Wuthering Heights and Withnail from Withnail And I.