The simplicity of summer dressing is liberating for a while, but it’s not long before wearing basically the same thing every day starts to feel a little stifling. That’s why we’re always so thrilled when fall comes around and we’re able to experiment with layers, textures and longer shapes once again.

With the cooler weather just around the corner, now is the smartest time to start thinking about what to keep in your wardrobe and what to add for the coming season. There are plenty of fall staples you’ll want to make sure you’ve checked off, as well as some timely, trend-led pieces you may or may not wish to add to your cold-weather rotation.

To give you a head start, we’ve pulled together this handy edit of our favourite fall fashion essentials, covering all the key pieces you need to be well dressed as the leaves begin to turn.

Work Pants

Looking for some comfortable, practical legwear to see you through fall and winter? Get yourself a pair of proper work pants. Bonus points if they’re thrifted. Vintage Carhartt Double Knee pants are still having a moment, and look great with similarly burly pieces like heavyweight hoodies and sweats, thick outerwear, and textured knitwear.

If you can’t find those exact pants, just look out for anything with a straight leg, a few extra pockets and in a thick fabric like cotton drill or even a heavy twill.

Hairy Knitwear

Love it or hate it, mohair madness is still going strong. Fluffy, textured pullovers and cardigans remain some of the hottest items when it comes to tackling the cold weather in style this year.

Brands like Needles, Missoni, Beams Plus and Marni have some of the best options, but the trend is becoming so widespread at this point that you’ll struggle to find a contemporary menswear label not making some form of fuzzy knitwear.

Long Outerwear

Knee-grazing outerwear is very much en vogue this coming fall, and we couldn’t be more pleased about it. A long coat, like a mac or trench coat, is perfect for throwing on over anything and everything, and has a unique ability to lend even the sloppiest of outfits an air of elegance and purpose.

A good trench is something you can wear over your best tailoring on a rainy day, but works equally well with a hoodie, joggers and a pair of sneakers. And this isn’t just some flash in the pan either – buy well and you’ll still be wearing it decades from now.

Heavyweight Jersey Pullover

When it comes to hoodies and sweats for the cooler months, thicker is better. A proper heavyweight jersey pullover is a great layering tool on really cold days, and works excellently as a standalone piece in milder, cool weather.

Anything over 12oz will be super cosy, and if you go for a nice neutral colour then you’ll be able to wear it with most of your winter casual wear.

Rain-Friendly Deck Shoes

We’re big fans of the Ivy League resurgence that’s currently sweeping the menswear world, but while deck shoes are great, they’re not the most practical form of footwear in inclement weather. With a grippy, deep-lugged sole, this rugged update on the classic shape offers the same good looks in a more fall-friendly package.

There are a few versions around, but Timberland’s 3-Eye Lug Deck Shoe is the original and best.

Mid-Wash Jeans

Mid-wash denim is the perfect stepping stone between summery stonewash and wintery indigo. It’s subtle, versatile and ties in perfectly with the aforementioned trend towards Ivy League style and preppier pieces.

Naturally, there’s no shortage of options, but we’re really loving Japan’s OrSlow at the moment. The brand makes some seriously nice jeans, featuring premium Japanese fabric and meticulous attention to detail. Check out the 105 model for a good starting point – not too slim, not too baggy, with a classic straight leg and beautiful selvedge denim.

Textured Tailoring

Fall is a great time to start mixing some textures into your wardrobe, and tailoring is a solid place to start. Soft tailoring in particular offers a lot of room for manoeuvre in terms of tactile fabrics. Think heavy wool pants, unstructured corduroy blazers and knitted ties.

Just be careful not to over do it. And don’t go all in on earth tones either – too much of that and it’s far too easy to stray into geography teacher territory.

Puffer Jacket

A good puffer is your go-to, day-to-day jacket for fall and winter. It’s the sort of thing you can throw on over just a T-shirt and still be warm, and if you pick one that’s relatively subtle you’ll be able to wear it with almost anything.

We love The North Face’s iconic Nuptse jacket, but there are plenty of minimalist alternatives if you’d prefer something without obvious branding. Check out Arket and Adsum for some lovely understated options.

Heavy Flannel

A nice heavyweight flannel shirt is one of our favourite fall garments. There are so many different ways to style it, and it pairs well with pretty much any casual outfit you could think of.

Wear it open with a knitted pullover, over a T-shirt on milder days, or layer it up with a hoodie and some proper outerwear when winter comes around.

Lightweight Gilet

A thin insulated gilet is perfect for upping your layering game when the cold weather bites. It can be worn over a hoodie or crew neck to give your core some extra warmth, or layered with some light outerwear, like an overshirt, which wouldn’t be sufficient on its own. You can even wear it with tailoring. Choose something low-profile in a neutral colour and it’ll slot underneath a tailored jacket nicely.

Heavyweight T-Shirts

T-shirts are still essential items in fall and winter, but you’ll want to make sure they’re thick enough to deal with the colder temperatures. Arm yourself with enough good-quality heavyweight tees to layer with on a daily basis and cold-weather dressing becomes a lot simpler.

You can determine how heavy any given T-shirt will be by looking at the ‘GSM’ (grams per square metre). Anything 200 (6oz) or above is comfortably within ‘heavyweight’ territory. Take a look at Camber and 3Sixteen for some of the best, or Hanes’ ‘Beefy’ tees if you’re on a budget.

Work Boots

‘Work Boots’ is a pretty broad term covering any type of high-top leather, suede or nubuck footwear that’s built to take a beating. We’re talking thick uppers, heavy duty commando soles and bombproof construction.

They’re ideal for fall and winter as they offer a greater degree of weather protection than your average shoe or sneaker, and they look great with autumnal casual staples like jeans, flannels, fleeces and heavy outerwear too.