Autumn is a notoriously tricky period to shop for, not least because a typical autumnal day can be a stage for all four seasons, each one coming and going with little forewarning. So rather than thinking you need ‘autumn’ outerwear, instead consider ‘trans-seasonal’ pieces that could have your back most months out of 12.

Not only will you get more wear from them throughout the year, but they’ll also encourage you to better mix and match other elements of your wardrobe that you’d previously pigeonholed as ‘seasonal’. We’ve tracked down the nine must-have styles from the biggest autumn/winter trends to ensure your wardrobe doesn’t trip over itself this fall.

The Varsity Jacket

There has been a spotlight on varsity jackets recently as many luxury labels put their spin on the preppy/jock classic. It’s a versatile, youthful style, segueing between casual and elevated sportswear. If you’re searching for inspiration look no further than Ralph Lauren’s Letterman jacket; a trans-seasonal hero piece if ever there was one.

You couldn’t afford one of those on a student budget, though. Fortunately, there are plenty of other much more affordable options out there – especially from vintage stores – that will add a good dose of collegiate cool to a weekend wardrobe. Throw it on with just about anything, from jeans to track pants via tailored trousers. Playing in that many positions, the varsity jacket is this season’s MVP.

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The Bomber Jacket

Along with varsity jackets, bombers have been one of the most sought-after silhouettes for the last couple of seasons, precisely because they are so wearable in these athleisurely times we live in. You can find plenty of inventive styles and silhouettes (particularly longline) to elevate your streetwear look or even to dress down a pair of trousers and loafers.

“They look best when the layers underneath are kept simple,” says Sarah Gilfillan, founder of personal styling service Sartoria Lab. “If you’re afraid of them making you look chunkier at the waistline then search for ones with a looser rib hem or no rib at all and vertical slant pockets instead of patch pockets.”

Autumnal hues from greens to burnt orange offer a strong statement around which you can work more simple wardrobe staples such as plain tees, jeans and cropped trousers. Otherwise, there’s nothing wrong with playing it safe (and chic): a black bomber jacket as the centrepiece to an all-black outfit is a sartorial direct hit.

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The Chunky Cardigan

Okay, so they shouldn’t strictly be filed under ‘jackets’ but cardigans come in really useful on those blue-sky autumn days when there’s a pinch in the air. Wool is one of the best natural fibres for regulating body temperature but is often overlooked as a transitional fabric. It also has great insulating properties and at the same time is extremely breathable, plus you have the luxury of buttoning them up or down.

“This has to be a wardrobe staple for the autumn,” says stylist and personal shopper Daniel Johnson. “Great for getting out into the countryside and when back, sitting in a country pub next to a fire.” Shawl neck designs can be a warm substitute for a blazer and keep an eye out for belted versions too, which look just the right side of louche when worn with tapered jeans and Chelsea boots.

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The Utility Or Field Jacket

Although they fell from the same sartorial tree (the functionality branch to be precise), utility jackets and field jackets can serve slightly different purposes come the autumn. The former are the perfect addition to a slick modern wardrobe with a streetwear edge. They’re very much on trend right now and make for a great layering piece. Look for styles with multiple pockets and interesting zip details, all of which add a certain militaristic masculinity to your look.

The latter have a more refined heritage appeal, exemplified by Belstaff’s excellent two- and four-pocket waxed cotton collections. “Style it like an Italian by pulling it in at the waist and layering it over tailored trousers, a shirt and half-zip fine knit sweater,” says Gilfillan. “Or go more casual with a chunky knit sweater and jeans for the weekend. Look out for versions with epaulettes if you need to visually broaden your shoulders.”

Both styles are typically cut from technical or treated fabrics making them waterproof, lightweight and ideal to see you through the winter.

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The Down Jacket

Once the preserve of adventurers, explorers and bird watchers, down-filled jackets have become the fashion industry’s favourite functional design with the likes of Cottweiler and Craig Green creating some innovative shapes this season.

Of course, the beauty of down-filled styles is their weight – or lack of it – and ease of wear. These days, virtually every jacket silhouette you can think of now comes in a down version, while labels such as Brunello Cucinelli have been styling padded gilets beneath suit jackets, such is their versatility.

We love the classic hip-cut style worn with a pair of jeans and some hiking boots. It’s an understated look but it comes off looking rugged and original (see Daniel Craig in Spectre). You can spend a small fortune on brands like Moncler, Stone Island and Herno, but check out lesser-known labels such as Colmar and Save The Duck who make some amazing affordable pieces, or high-street fall-backs like M&S and Uniqlo. Insulation has never looked so good.

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The Technical Jacket

Technical fabrics make for excellent autumnal jackets given their superior weather-beating properties. With many luxury labels channelling streetwear right now, together with a stack of high-profile collaborations from the likes of White Mountaineering x Adidas and The North Face x Junja Watanabe, technical jackets have seamlessly transitioned into the athleisure trend.

To ensure you don’t look like a hiker that’s taken a wrong turn, opt for a slightly oversized design that you can wear unzipped with multiple layers underneath. It’s not a look for everyone (we can see sartorial types baulking now) but it will garner some streetwear gravitas when combined with track pants and trainers.

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The Trucker Jacket

Corduroy is set to be a big hit this autumn: the ridged fabric beloved of geography teachers stepped out onto many a runway earlier in the year, not least at Prada where it was the focus of the entire collection. If you’re not quite ready to stride out in a pair of mustard yellow cords, then think about opting for a hip-length trucker jacket.

“The trucker jacket has been a casualwear staple for more than 150 years, and is perfect for layering in the colder months,” says Olie Arnold, style director at Mr Porter. “Though more commonly seen in denim, velvet and corduroy options offer warmer qualities for cold-weather dressing.”

It’s a neat slice of Americana workwear that’s easy to wear with a pair of jeans and hiking or Chelsea boots.

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The Biker Jacket

Cut short, asymmetric, and close to the body, the leather biker jacket has proven to be one of the most timeless pieces of menswear. It’s one of those trans-seasonal hero pieces that can be thrown on with absolutely anything and instantly makes you look degrees more bad-ass.

Go for black leather with silver zipper details to stay true to the classic Perfecto styles of the 1950s, but also look out for distressed leather versions, painted graphics and wool iterations this season.

“I have a long version of a biker jacket with a shearling lining, very fitted through the waist,” says Johnson. “This goes fantastic with a pair of grey moleskin trousers and Hunter wellies. If it’s not so damp I’ll put on my chunky Hackett ankle boots.” Yes, you might have to spend good money but these really are jackets for life.

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The Shearling Jacket

From Peckham’s Del Boy to Beckham’s Kent & Curwen, the shearling jacket has ridden a rollercoaster of trends, but it seems that the warm sheepskin style is finally here to stay.

Ever since it was worn by American fighter pilots in the 1940s and subsequently Hollywood stars reenacting battles in the skies in the 1950s, shearling has always had a very masculine look about it. The smooth finish juxtaposed with the furry collar and lining somehow combine to create natural sex appeal.

Not so sexy is the price: there’s no way around it, a shearling jacket is a big-ticket item that will often set you back four figures (or three if you go for high-street shearling-effect versions), but rest assured it’s money well spent. The two main styles to look for are the straight zip-up and the biker zip-up, both cut short to the hip. Any longer than that and you venture into 1970s football manager territory.

“Try layering over a medium-gauge knit for a refined take on cold-weather dressing,” says Arnold. “Teaming the jacket, with its plush interior and oversized collar, alongside denim and chunky boots will have you snug and ready for the biting weather as the temperature drops.”

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