Autumn/Winter Layering Combinations For Menswear

Feeling a nip in the air? You’re not the only one. With autumn wasting no time in sending the sun packing, staying warm is quickly becoming priority number one. But piling on the entire contents of your wardrobe isn’t exactly the stylish solution. Yes, trapping heat is essential, but get excessive with your layers and you’ll be sweating like a turkey on Christmas Eve. Instead, use our cheat sheet and you’ll not only look on-point but be well-equipped to beat the elements, too.

Shirt + Overshirt

The perfect combo when a jacket is too much but a shirt is not enough; doubling-up up top with a button-down shirt and twill or flannel ‘shacket’ is an ideal move to pull in the early days of autumn. Just don’t do a Steve Bannon. Wear an overshirt either buttoned up or undone (the latter being less formal) and the sleeves down or rolled (ditto), depending on what the day throws at you. Teeth still chattering? Try adding another layer in the form of a T-shirt underneath your shirt.

how to layer shirts with overshirts in autumn

Shirt + Jumper + Blazer

With office wars over air conditioning a year-round fixture, use these put-on, peel-off wardrobe staples to easily switch between extremes. Lay the foundations with a well-fitting shirt in a neutral colourway (deploying the military tuck if necessary) and follow up with a fine to mid-gauge jumper (ideally in a breathable fabric like merino wool) and a single-breasted blazer cut with just enough room to accommodate the underlying layers. For a final touch of sartorial nous, add a scarf into the mix, either wrapped neatly or draped loosely around your neck.

how to layer a shirt, jumper and blazer for autumn

Shirt + Shawl Collar Cardigan

A raffish alternative to the standard office rig, a plain-coloured or check shirt worn with a chunky shawl collar cardigan is cold-weather smart-casual dressing at its finest. This pairing alone will serve you well indoors, but braving the elements calls for reinforcements. Throw over a cropped parka or quilted jacket to chill-proof your look without sacrificing style. Where the finished look falls on the smart-casual spectrum can be dialled up or down based on what it’s worn with – chinos and boots appearing more dressed up than jeans and sneakers.

how to wear a shirt and shawl collar cardigan for autumn

T-Shirt + Shirt + Bomber Jacket

Part skate, part street, this fail-safe mash-up offers all of the comfort of casualwear, but doesn’t make you look like you’ve stumbled out of the house in search of a pint of milk. As a general rule, layers should get thicker the further away they are from the body; so start with a crew neck T-shirt and build up with a heavier, cold-weather shirt (twill, denim, Oxford and flannel styles all fit the bill) worn open. Don’t try to repurpose your nine-to-five button-downs here: cotton dress shirts are too fine and fitted for this job. Polish it all off with a bomber jacket in cotton, nylon or leather for an effortless approach to off-duty layering. For a Kanye-approved edge, try ‘reverse layering’ by opting for a longline T-shirt under a shirt that falls between the tee and jacket.

how to layer a shirt and bomber jacket for autumn

Roll Neck + Overcoat

If there’s a more polished way to ward off polar temperatures, then we don’t know it. Having muscled its way to become a true menswear mainstay, if you only add one knit to your wardrobe this autumn/winter, make it the roll neck. Warm, elegant and a hell of a lot easier than messing around with buttoned cuffs, a roll neck makes a sophisticated and hassle-free alternative to a shirt, and looks its least ‘drama tutor’ when paired with an overcoat. To tie the look together, consider going tonal up top with a royal blue knit under navy outerwear, or set off a camel coat with a rust or burnt orange design.

how to wear a roll neck with an overcoat

T-Shirt + Denim Jacket + Overcoat

Mixing two very different pieces is a solid way to take your layering game to the next level, but doing so is not for the sartorial newb. Striking the perfect balance between a denim jacket and tailored overcoat is no mean feat – everything from fabric thickness to cut and colour needs to be on-point for you to stand a chance of pulling this one off. Game for the challenge? Start with a simple T-shirt that works with each layer of the outfit individually, add a slim-cut denim jacket (avoid chunky selvedge or sheepskin-lined designs) and round out with a wool overcoat that’s minimal in both its design and weight. Not an overcoat kind of guy? It’s also possible to sub in a lightweight trench coat, mac or technical jacket over the top instead.

how to wear a denim jacket under an overcoat

Suit + Tracksuit Top

Tailoring purists, look away now. Not content with swapping a shirt for a T-shirt or brogues for trainers, the menswear world has taken the suit fully off-piste with the introduction of the tracksuit top. Tapping into the trend for high-low dressing, this sportswear-meets-suiting hybrid is dragging traditional tailoring into the present, while also making a cold neck on the commute a thing of the past. Nailing this look is all about subtlety. Stick to fairly conservative colours (navy, black, grey) for the suit and lean towards premium zip-ups in complementary colours rather than taking the 1980s footballer route.

how to wear a tracksuit top under a suit jacket

Roll Neck + Jacket

Rocking a roll neck doesn’t have to mean looking like a Bond villain. Thankfully, northward-creeping knitwear works just as well under a cropped jacket as it does a blazer. The appeal of this pairing is that it hits the sweet spot between looking like you’ve made an effort but not looking like you’ve made too much. And in our book that’s pretty much the holy grail of menswear. Whether you opt for a leather biker or shearling-lined flight jacket, switching up the thickness of your knit allows you to control how smart or casual it skews.

how to wear a roll neck with a jacket

Hoodie + Overcoat

Once the uniform of angst-ridden adolescents, now a stylish way to swerve a case of sartorial SAD, the hoodie is all grown up and fully menswear approved. A hoodie on its own won’t win you any prizes, but chuck an overcoat into the mix and things get considerably more exciting. Rainproof, coldproof and even boss-proof in a business-casual office, it’s as close as you’re likely to get to the perfect couple. It’s not as simple as digging out your old university sweat, though. To make this outfit appear less like a mid-life crisis, smarten up your act with a slim-fitting style cut from a premium material like wool or brushed cotton and leave any logos to the interns at work.

how to wear a hoodie with an overcoat

Shirt + Gilet + Blazer

Following years in the menswear hinterland, gilets are back, and on more than just flat cap-wearing farmers. Owing to trends like athleisure – they’re now a stylish option for when you need to stay warm. Done right, this triple threat adds an extra slice of insulation to your officewear that’s particularly welcome on the brisk morning commute. Key to carrying this one off is finding a slim, lightly padded and, above all, understated design. The gilet’s job here is to keep out the cold and lend a contemporary edge to your tailoring, not make you look like you got lost somewhere between the mountain range and the water cooler.

how to wear a gilet with tailoring