8 Winning Combos You Can Rely On

When the cold starts to bite, layering becomes a practical necessity. It allows you to adjust your temperature throughout the day, which is invaluable on awkward transitional days, and it keeps you better insulated in the most bitter temperatures by trapping pockets of warm air. But it’s not all about practicality – layering is also an art form when it comes to styling.

Not only does layering allow you to dial up the warmth, it also allows you to dial up the depth and visual interest of your outfit. It’s a chance to introduce different textures, colours and shapes, building a look that’s greater than the sum of its parts.

The trouble is, it can be difficult to wrap your head around if it doesn’t come naturally to you. But luckily, there are a number of go-to combos you can fall back on when in doubt. Below are a few of our tried-and-tested favourites.

Heavyweight Hoodie + Liner Vest

One for the weekend on autumn days when the weather’s neither here nor there. Simple but effective, it keeps the torso toasty while allowing you to create strong tonal contrast. The heavyweight hoodie works on its own when you step inside, and the coat adds insulation where it’s needed most while leaving arms unrestricted.

Go for a well-fitting grey hoodie. Anything oversized will be trickier to layer over, and the light neutral colour keeps your colour options open for the vest. Go for a bold pop of orange or red if you’re feeling adventurous, or keep it muted with brown, olive or black.

We’d also suggest selecting one with a two-way zipper or poppers, so you can undo it from the bottom for ventilation or easy pocket access.

Crewneck Knit + Worker Jacket

Slightly more grown-up, but also weekend appropriate, this classic combination is about as ‘timeless’ as they come, pairs well with almost any legwear style and works in a variety of colour combinations. Wear it with jeans for everyday style, or combine it with pleated wool pants and chunky Derby shoes to level it up.

If you go dark with the jacket, go light with the knitwear, and vice versa. A khaki overshirt—the most reliable light jacket in menswear—and a cream crew neck are always a winning combo. Think a nice heavy Aran sweater if it’s winter, or a fine-gauge merino in the autumn.

For bonus points, pick one in a nice flecked wool for added personality.

Rollneck Sweater + Leather/Suede Jacket

Taking the formality up a notch while still keeping it cool, a rollneck paired with a leather or suede jacket is the perfect option for evenings out, date nights, and the like. It’s smart, but not too smart. It shows you’ve made an effort, but you’re not trying too hard.

Again, contrast is key, but it doesn’t have to be stark. The smarter you want to look, the darker the palette should be. A beige knit layered under a tan jacket, for example, feels more relaxed than a charcoal knit worn under a black jacket.

When it comes to the outerwear, don’t cheap out – spend a bit extra on a proper leather jacket and it will likely outlast you.

Plain White Tee + Heavyweight Flannel

From sleek and sharp to the exact opposite. This workwear-inspired duo is the perfect complement to a pair of heavyweight raw denim jeans and your trusty leather moc-toe boots. The key is to buy quality and pay attention to fabric weight. Go heavy for the tee and even more so for the shirt.

Go for 200GSM as a minimum for the T-shirt. Buying online is fine, but with pieces like this, where the fabric weight is so crucial, it’s always nice to actually get the garment in hand before parting with your cash.

Flannel-wise, shop brands such as Filson, The Real McCoy’s, Iron Heart and The Flat Head, and you can’t go wrong.

Oxford Shirt + Crewneck Sweater + Overcoat

Here’s one for the office. A weather-ready combination that can tackle everything from extreme cold to client meetings without missing a beat. Whether you’re wearing all three at once, just the knit and shirt or the shirt on its own, every layer you peel back reveals a look that works on its own, and that’s why we love it.

For the shirt, a classic white Oxford will do; no need to complicate it. Contrast it with a navy or charcoal crew-neck knit so that the white of the collar can creep past its neckline.

When it comes to the overcoat, think heavy and woollen in a textured, patterned fabric, like a Prince of Wales check or similar. Something roomy enough to throw on quickly without having to wrestle.

Chunky Knit + Waxed Jacket

Both pieces are born weather busters, but neither can survive on its own. Bring them together, however, and they’re a formidable duo – one trapping the body heat and the other providing an impenetrable barrier to wind and rain. Oh, and they look great too.

A chunky knit in a light colour is the way to go here. Pick something ribbed or with cable detail, depending on your style. For the jacket, go dark. Navy and olive are classic, but brown, burnt orange and mustard are all solid alternatives if you want to keep the palette autumnal.

Lightweight Puffer + Technical Rain Shell

Whether you’re off for a hike or just leaning into the outdoorsy aesthetic, a waterproof shell and a puffer jacket is a functional pairing that will protect you from the elements like nothing else. Think of it as the modern alternative to the waxed jacket and knit further up the page – the shell blocks the wind and rain, while the puffer provides the warmth.

Starting with the puffer, you’re going to want something relatively low profile so that it doesn’t hinder movement when you throw the shell on top. Something like Arc’teryx’s Atom Hoody or Patagonia’s Nano Puff would work well.

When it comes to the shell, you want ‘waterproof’, not ‘water-resistant’. Think taped seams, waterproof zippers and an adjustable hood.

Shirt + Crew-Neck Knit + Blazer

When you need to look put together, this combination never fails. It’s sharp and tailored, but the knit adds an extra layer of warmth. Not only that, it acts as a vehicle for colour, texture, or even a bit of pattern, allowing you to inject a bit of personality into an otherwise fairly stale format.

Texture and structure should reflect the formality of the setting. If you’re working a corporate job, think poplin dress shirt, fine-gauge knit and a classic blazer with some shape to the shoulders. For more relaxed environments, you could opt for an Oxford shirt, a chunkier knit and an unstructured blazer in corduroy or tweed.