How To Layer Every Jacket In Your Wardrobe

It’s officially layering season, when we’re all exposed to cataclysmic changes in temperature every half an hour and battles over office thermostats turn deadly. It’s at this time of year when you have to deploy your most cunning fashion moves, creating coordinated outfits with more layers than an emotionally intelligent onion.

Of all the layering pieces you own, your selection of jackets will be the most versatile. They can work as your outermost armour when the weather is so balmy that you don’t need much underneath but they also slot in-between your tees and top coats when more layers are called for.

Here’s how to get even more wear from every cool jacket hanging in your wardrobe.

CHORE COAT

Few jackets can be worn in quite as many ways as the chore coat. Usually unlined and in a hard-wearing fabric such as cotton drill or moleskin, it’s ideal for a range of casual looks from all-out workwear through to off-duty tailoring.

It can also be layered under a heavier garment, or over something lighter such as knitwear or a gilet. Due to its boxy cut it can easily accommodate a chunky roll neck underneath, or an equally functional utility vest if you want to maximise the pockets available to you.

Try going full early-20th-century-factory-worker and pairing yours with cotton work trousers, complete with double-stitched pockets and wide cut for ultimate comfort. Underneath go for a zip-through waistcoat in seasonally appropriate tartan fleece, which’ll both keep you warm and add a welcome pop of colour.

TRUCKER JACKET

The hardy perennial of casual dressing, the trucker jacket thrives out in the open all year long. It sits atop tees and shirts during the warmer months but really shows what it can do with autumn and winter layering.

When it’s cold outside, the most obvious way to wear a denim jacket is over a sweatshirt, fisherman knit or hoodie, trapping the heat from your knitwear. The look works with chinos but for best results lean into the style’s workwear origins and go double-denim.

If you want to mess with convention, however, wear your trucker jacket as a mid-layer instead. Buttoned up under a boxy mac or spacious overcoat, the effect is unexpectedly pleasing on the eye and it lets you mix fabrics while you’re at it — a key skill in any layering game.

WINDSTOPPER

Wind-stoppers stop wind — it’s in the name. But the lack of padding isn’t exactly designed to keep you snug underneath. That’s where it’s useful to pull them into a layered look, with a mighty padded coat over the top, bringing the heat and sucking you into a duvet in which you can spend your winter days.

An arctic parka will fit the outerwear vibe, preferably one in a versatile black or navy. That way you can experiment with your wind-stopper colour underneath. Pick one without a hood, or at least a detachable one. The thicker material on your parka will make for a better hood, and having two hoods flying behind you can be annoying.

Keep the outerwear vibes running downstairs with a pair of on-trend and hard-wearing cargo trousers, and some similarly en vogue hiking boots. With the outdoors look so popular at the moment, it would be rude not to.

OVERSHIRT

The overshirt can be treated in a similar way to the chore jacket in that it can worn in a hundred different ways. Open over a T-shirt, buttoned up under an overcoat, or even worn over a lighter shirt, it’s the utility player capable of doing it all.

The latter option may be the easiest way to layer on this entire list, but there are some tricks to it. First of all, the overshirt needs to have a slightly boxy, almost oversized cut, which will allow it to be worn over another shirt. Secondly, pay attention to fabric. The overshirt should be made from a heavier weight fabric than the shirt worn underneath to differentiate the two — think cotton drill or canvas.

For ultimate layering points though, wear both shirts under a proper coat. As an overshirt is nearly always unlined it will sit well under a parka or unstructured overcoat, offering not just extra insulation but extra storage in the form of chest pockets, too.

PADDED GILET

The gilet has to be a bit of a one-off in men’s fashion, in that it’s as popular with bankers and political strategists as it is with anarchists and warcore fans. Granted, these somewhat divergent style tribes have their own ways of wearing them, but what they all agree on is that it’s a supremely snug and practical layer.

At the smarter end of things, the idea is a simple one: you make your tailoring a little toastier for the commute by slipping the gilet under your blazer or overcoat, giving your outfit a pleasing high-low quality in the process. Then you take it off again when you get to the corner office.

In more casual circles, where traditional outdoor performance gear is fast becoming must-have fashion, the look is all about techwear. Combine your gilet or vest with thermal tops and waterproof outerwear that could see off an Icelandic winter, even if you don’t intend to leave the city. Look for dramatic silhouettes and keep the palette muted — all-black ninja chic is preferable.

WAX JACKET

No jacket has more of an association with the British countryside and the bitter weather that dwells on our rolling hills, than the waxed jacket.

It’s hard therefore to take it away from the very British farmer’s uniform. We’d avoid the flat caps and walking stick — too much like a costume for its own good — but instead plump for a modern smart-casual wardrobe of turtlenecks, fine knitwear and crisp, cotton button-downs underneath.

Swap in a subtle graphic sweatshirt for your regular wool jumper for a sportier, streetwear vibe while still maintaining a degree of smartness. On your feet, ditch the wellies, and instead pick up a pair of chunky leather boots with a stand-out sole — they’re this season’s must-have and can be smartened up or down depending on your ‘fit .

It’s not too much of a drastic change from the farmer’s uniform sure — but we’re not trying to overhaul the formula here; merely updating it.

BOMBER JACKET

Bomber jackets come in a wide range of styles, from World War I-style leather pieces through to ’60s jet-era MA-1s made from nylon. Unless you’re going for a period look or want to incorporate vintage clothing into your wardrobe, it’s best to look for aviator-style jackets, which are inspired by these historic styles but feature updated details and more modern fits.

Look for styles based on the MA-1 bomber but with a more minimal design, which makes them far easier to layer. Ideally, you don’t want the traditional arm pocket, wide cut and interior wadding, just a well-cut jacket that sits much closer to the body and will rest under a larger jacket with ease.

A bomber such as this is ideal for placing under a longer overcoat or raglan-sleeve raincoat. Keep the tones of both dark and simply remove the coat when indoors for a classic look inspired by the menswear heroes of yesteryear.