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It’s easy to romanticise autumn dressing. From shows such as Gilmore Girls and Sex and the City, cosy Meg Ryan movie masterpieces, including Sleepless in Seattle and You’ve Got Mail, and social media, you’re given the illusion that the season mainly consists of sauntering along leaf-strewn streets, pumpkin spice latte in hand, while wearing snug layers.
The reality is more startling: getting up in the dark, leaving the office in the dark, arguments about whether it’s too soon to turn on the heating, and growing bored with eating soup.
Now, while we can’t help with the drop in serotonin levels, we can help with those grey mornings when even the dog doesn’t want to go out. Getting dressed in the dark means you’ll need pieces that you don’t need to think about. A striped shirt. A cashmere jumper. Tailored trousers. And piles of leaves that look pretty in the sunshine but turn to mush in the rain require harder-working footwear – so how about a biker boot? These are the wardrobe heroes you’ll end up easily mixing and matching day after day.
Then there are the wardrobe extras that make your look feel a touch more special: tinted glasses, jazzy socks, cheerful-making jewellery … because, let’s face it, winter’s coming and you have to get your mood-boosting kicks where you can.
Women’s wardrobe updates for autumn and winter
Knitwear nod to the 90s
Burberry on a budget. This jumper’s slouchy fit, longer-length sleeves and side splits give a nod to the 90s grunge aesthetic, which is enjoying a resurgence on TikTok. The zingy colours work nicely with a black leather skirt or just dark jeans.
Checked jumper
Sweet-but-not saccharine midi
With pleats, bows and buttons, this midi skirt is sweet, though its manzanilla olive colour and tough organic cotton prevent it from veering into saccharine territory. Wear with boots that add a little attitude: think knee-high leather or chunky buckled biker versions.
Midi skirt
Ballet trainer
Portmanteaus in fashion are two-a-penny, but every now and then a useful one comes along. The sneakerina has all the practical elements of a sneaker – a supportive footbed and sole that doesn’t disintegrate in the rain – but with the added elegance of a ballerina flat. Try it out as an unexpected evening shoe.
Sneakerinas
T these up
Over at the Row, the Olsen twins’ fashion label, models wore boxy T-shirts over long-sleeved tops – so now we wear boxy T-shirts over long-sleeved tops. Experiment with tonal trickery by wearing a dark green T-shirt over the top of this khaki striped version.
Stripe long-sleeve T-shirt
Top of the Topshop
One of the best pieces to come out of Topshop 2.0 is this weighted miniskirt with a colour-run pattern and a nice kick. The waistband means it works if your top is tucked in or out, or at half mast. Wear with chunky boots.
Knitted mini
Cowabunga!
Puma Speedcats are a gen Z favourite, especially when worn with baggy jeans. However, when paired with tailoring – see the Ahluwalia catwalk – they work just as well for the office too. As for the cow print, when did you ever see it on a shoe? Guaranteed to liven up any neutral outfit.
Puma Speedcat cow-print trainers
In the trenches
Trenchcoats are surprisingly hard to pull off. Get the wrong shade of beige and you look washed out. Get something too simple and it can suck the fun out of your outfit. With its check collar detail and dark beige tone, this is a genuinely great transitional coat.
Check-trim trenchcoat
For more, read our guide to the 50 best coats for autumn and winter
Derby day
These are great, chunky-soled, puddle-proof back-to-school Derby shoes that are also surprisingly comfy.
Noreen shoes
Boots made for walking
Boots for when your weather app says 90% precipitation. Wear with a romantic dress, a silly mini or sensible midi, or even wide-leg trousers. No faffing around with zips – just pull them on. Plus, the memory-foam-padded insole means no end-of-day leg ache.
Biker-style boots
Office and home wear
A knit that hits that smart/casual sweet spot. For the office, try buttoning it up and popping under an oversized blazer. For weekends, wear with loose-cut jeans, then accessorise with a stack of newspapers and a roaring fire.
Knitted polo shirt
Waxed lyrical
This cropped style is a nice alternative if you find a traditional trenchcoat swamps you. The cinching belt and exposed back panel detail allow you to add even more shape.
Waxed coat
Earn your stripes
An autumnal spin on soft-power dressing. This shirt has a slightly longer cut, so it allows you to experiment with proportions. If you usually wear your shirt tucked in, try untucking it and vice versa. On colder days, wear it buttoned up over a roll neck.
Striped shirt
Mess your collar up
At Dior, Jonathan Anderson half-popped the models’ shirt collars. Try it out by leaving one side of a shirt collar poking up and out from underneath a sweater.
Nordic knit
It has been almost 15 years since Sarah Lund burst on to our screens in The Killing, but we’re still thinking about the detective’s chunky knitwear. This Fair Isle jumper may be made in Scotland from 100% brushed lamb’s wool, but its bronzy gradient colour effect and cosy fit give Nordic vibes.
Fair Isle lamb’s wool sweater
Stud u like
Main character energy in skirt form. Wear with a simple white T-shirt or plain knitted jumper to ensure it remains the centre of attention.
Studded miniskirt
Bring to heel
Not cheap, but we know you’ll end up justifying them using the cost-per-wear concept, thanks to their walkable block heel and smooth leather that moulds around your foot. Further reasoning? The square toe shape means less scuffing than if they were pointed, and the higher cut means they will keep you warmer.
High-front block heel
Smart denim
Ideal for those who want to do tailoring, though not in a traditional sense. More unusual than a fitted blazer, but in a fabric familiar enough not to make you feel too on edge. Looks smartest when worn as a Canadian tuxedo with matching jeans.
Denim tailored jacket
V for victory
Not cheap, but guaranteed to become one of the most worn items in your wardrobe. Knitted from a blend of merino wool and cashmere, this jumper is cosy but still breathable – an important factor to consider if you are engaged in an on/off central heating battle. Thick rather than flimsy, it will sit well on the body. Plus, the structured V-neck and ribbing are lovely details.
V-neck jumper
Polo explorer
A collarless polo shirt was the OG uniform of Henley rowers. They have moved on to tech sportswear, but the shape remains timeless. With its raglan sleeves and multiple front buttons, this version is a perfect layering piece. Wear over a long-sleeved cotton top or lace cami.
Cashmere Henley
Lace and favour
Glimmers, those tiny micro moments of joy, are even more important at this time of year, and a fun pair of knickers is a good starting point. These are made from recycled lace and Tencel, a semi-synthetic viscose-style fabric that’s more sustainable than regular viscose, so that’s another win before 9am.
Lace knicker
For more, read our guide to the best women’s underwear for every occasion
Anytime dress
Clothes need to earn their place in your wardrobe. Some easy styling tricks will make your party dresses work for daytime. A roll neck under this satin dress or boots and a chunky jumper over it will kill off the evening-only vibe.
Striped satin dress
Vest to impress
If you run hot, then a sweater vest rather than full-on sweater could be the solution to winter layering. Wear over a T-shirt, shirt or dress without feeling constricted. This one has bows, which are always a sweet bonus.
Bow side vest
Bossy boots
Instead of a party heel, may we suggest a party boot? You don’t have to worry about someone spilling a drink on your exposed foot, compared with, say, a satin pump. This studded pair is also ideal if you are going straight from the office, as they work nicely with smarter tailoring, such as a wide-legged trouser.
Studded kitten heel boots
Slip on something chunky
Upgrade that flimsy pair of slippers you nicked from your last hotel stay with a chunky slip-on in a bright print.
Printed slippers
Quilt while you’re ahead
Because a quilted jacket doesn’t have to mean gorpcore. As the clocks go back, the blue paisley print on this one is akin to a shot of serotonin. Plus, it’s got a lovely contrasting gingham lining so you can roll the sleeves for an easy pattern clash.
Paisley print jacket
Chill with style
You can wear them to pilates. You can wear them for Netflix binging. Just a really comfortable and versatile pair of joggers that feel just a touch more special than your old trackiebums.
Knit trousers
English flannel
Maybe Yellowstone is to blame, but the flannel shirt is enjoying a newfound cult status. Wear unbuttoned over a T-shirt. Or, in place of a belt, wrap a flannel shirt around your waist to break up an outfit and add definition.
Flannel shirt
Two-tone neon pop
A useful layering piece. The pop of neon around the collar will look great peeking out from underneath a dark coloured jumper.
Two-tone turtleneck
Rib rolled
Amy Powney is a London-based fashion designer who regularly calls out the industry for greenwashing, so you know when she does a collaboration she’ll scrutinise every detail. This jumper from her partnership with the Cornish label Finisterre is made from 100% merino wool, so it will keep you warm and, unlike polyester mixes, won’t make you sweat.
Roll neck jumper
Weighty and wide
Front pleats make trousers instantly look smarter. Also, these are made from weighty fabric, which means they will hang nicely over footwear and not flap around so much on a breezy day.
Wide-leg trousers
One coat to see off winter
Let’s face it, you’ll have to wear your winter coat day in and out, so choose one you won’t grow bored by after the first week. This grey version will go with everything, and you can easily brighten it up with a jazzy scarf. The maxi length makes sense: no one enjoys cold knees.
Wool blend coat
Swap your socks
Still wearing your loafers/trainers with an invisible ankle sock? It’s time to let them go. Instead, you need a purposely visible sock. It can be tall or slouchy, but it needs to be seen. Zoë Kravitz and Hailey Bieber like to wear their black loafers with white ribbed socks, while at the recent shows, the street-style set tested out everything from block colour pairs to patterned. We also spied one show-goer in a cashmere bed sock. There are no rules!
Socks and the city
As the temperature drops, swap wafer-thin merino versions for thermal. These are still slim enough to wear with loafers and even chunky sandals, and the argyle print is instantly cheering on dark mornings.
Heattech socks
Lace the competition
Miu Miu’s trainer collaboration with New Balance may have sold out within minutes, but you can easily replicate the look. Rather than one pair of single-coloured laces, the trainers featured two-tone laces. It’s pretty self-explanatory, but social media is peppered with tutorials if you want some more inspiration.
Danner gold and tan laces
In plain tights
The pink tights on Prada’s autumn/winter catwalk were a joy to see, but colourful tights aren’t for everyone. These are 30 denier, which means they keep out the wind but won’t colour-block your legs, which can make your outfit a little too “fun”.
Burgundy tights
Scrunch bunch
The easiest way to make a messy up-do look deliberate. The polka dots are also giving 90s minimal meets Pretty Woman, which is very now.
Satin scrunchie
A great headwear combo
Paloma Wool is one of the most criminally underrated knitwear brands. Just look at this – it’s a hat and scarf in one! Or rather, a bonnet for people who don’t want to wear bonnets.
Knit bonnet
One letter you’ll want to receive
An investment, yes, but it’s pure lamb’s wool, made in Scotland, and the personalisation means you’re more likely to look after it.
Monogram scarf
A fair clip
The Scandi street-style crew know a thing or two about dressing for the wind and rain. Their No 1 accessory? A vibrant-coloured claw clip that not only stops your hair from becoming knotty as you battle the elements but also adds a fun touch to more minimalist looks.
Chequerboard claw clip
Puffy, and plenty of pockets
Forget Hermès: when it comes to cult bags, Uniqlo is on a winning streak. After its bestselling banana shape comes a puffy shoulder bag that can fit a laptop. It also has two pockets each on the outside and inside, which is never a bad thing.
Shoulder bag
Think beyond the belt loop!
Pop your favourite belt over an oversized blazer, cardigan or even coat to add definition. It doesn’t have to match. Think a chocolate trench plus a burgundy belt, a denim jacket clashing with an animal-print belt or a charcoal blazer cinched with a studded belt.
Hip to the game
If Shakespeare was around today, he surely would have been down with wearing your heart on your hips (rather than your sleeve). This belt promises to add an element of fun to the most basic of looks.
Heart stud belt
Grin on a ring
“Cheer up, love” via your phalanges. This colourful gem ring is sure to make you grin every time it catches your eye.
Smiley face ring
For more, read our guide to the best affordable jewellery brands
Be there and be square
There’s been a lot of talk about tablescaping, but have you heard of table-top dressing? Don’t worry, it’s got nothing to do with napkins and flowers and everything to do with jewellery. The concept is simple: when going for dinner, just think about the accessories that will be seen from the waist up as you’re sitting down. These statement resin earrings will make even the most boring of T-shirts feel a bit jazzier.
Green square earrings
Hoop for joy
Pieces of glass, wood or crystal dangling from a corded necklace have usurped the nameplate as the new neck must-have. If it looks like something a boho art teacher would have worn in the 1970s, you’re on the right track.
Pendant necklace
I heart this pouch
Looks nice on a bathroom shelf. Looks nice on a desk. Looks nice in a suitcase. Useful for storing everything from skincare to charging cables.
Heart pouch
Every time’s a charm
A teeny tiny heart in an abstract shape that gives it a welcome edge.
Heart charm necklace
Strut your chunky stuff
Sunglasses with a warm tint are an easy way to soften grey days. These ones come with 100% UV protection, which is rare for the price.
Aviator-style sunglasses
My cherry (and Apple) amour
An AirPods case for those who live in constant fear of losing them. The pearlescent finish and tactile cherries mean you’ll find this in seconds rather than rooting around the bottom of your bag for several panic-inducing minutes.
AirPods case
Sorted for depills
Don’t buy new jumpers every year: just depill last year’s for a new lease of life. Alas, this doesn’t stop the moths.
Russell Hobbs fabric shaver
For more, read Jess Cartner-Morley’s October style essentials and how to celebrate the season of the witch
