Whether it’s a two-in-one coat or a truly delicious handbag, add some fun to getting dressed during the cold, dark months with our expert’s favourites

The best women’s shoes and boots for autumn

The clocks have gone back. The mornings are cold and the evenings are dark. The world seems to be doing its level best to discourage any fashion ambition beyond the need to stay alive and warm enough to function.

But clothes – even in winter – are not just about staying alive. They are about staying alive alive. Alive inside. So this month’s edit is about finding the fun in getting dressed when the weather is trying to discourage you. There is a pink jumper that manages to be both cosy and, well, slutty; a £16 henley that looks considerably more expensive than it is; and a skirt I have been stalking since the summer and can finally report back on. There are also ballet pumps with exactly the right amount of grownup elegance, a sweatshirt that makes a persuasive case for elevating the everyday, and a necklace to bring a bit of sparkle back to the proceedings.

I don’t have this yet, but I want it

Iris knit

I love a slutty jumper. Are we allowed to say that? I mean it as a compliment. A going-out top you won’t freeze in is perhaps more polite terminology. I want it in the cherry blossom pink, but it is available in lots of other nice colours.

An excellent value henley

There is something so classy about a henley. Like, when a character in a film is wearing a henley, you know it’s there to tell you this person has a good soul. When done with finesse – a superfine rib, delicate buttons – there is something quite sensual about it, in an old-timey kind of way. Anyway, this M&S version is amazing value.

A delicious handbag

Polène Cyme bag

Polène handbags are exquisite, which is why there are queues outside the Paris stores when new bags arrive. If you get a chance to swing by the Regent Street store in London, you will see what I mean.

A Christmassy pigeon

Pigeon tree bauble

Forget robins and turtledoves. Pigeons are the spirit animal of 2026.

Skirts are the new everything

Silk blend lace detail skirt

Wear a skirt. This is not a drill: Miuccia Prada says so. Skirts are so back, baby. I spotted this one, with its snazzy lace insert, back in the summer, when M&S womenswear head Lisa Illis was wearing it in the showroom, but it wasn’t yet on sale. I’ve been stalking it ever since; it’s now arrived, and I can confirm it is excellent.

Everyday elegance, yes please

Gathered back sweatshirt

The White Company strapline is “everyday elegance”, which feels like a policy we can all get behind. It has long been a go-to for chic home bits, but the new-ish clothing director Sheila McKain (ex of Jaeger and Donna Karan) is doing excellent womenswear too. The drawstrings at the waist here are great – I never like how a sweatshirt hem hits at the hip – and the gathering elevates it out of the ordinary.

Over a crew-neck sweater or with an open-neck shirt …

Lapis and blue sapphire necklace

Necklaces are having a moment again. I do find that a lot of pendant necklaces look a bit … babyish? Cutesy? Anyway, this gold-plated one is fab. Here in blues, but also comes in greens (aventurine and onyx) and reds (jasper and garnet).

Not all ballet pumps are created equal

Pointed leather ballet flat

I don’t like ballet pumps with bows on. So much chicer without. Massimo Dutti makes great shoes; I know I am repeating myself here, but I don’t think enough people know about the brand. These have an almond-shaped toe and a high narrow vamp, both of which give an elegant line. Available in black or burgundy.

Two coats in one

Wool coat

One coat, two personalities. A gorgeous, perfectly simple black coat with a luxuriously deep detachable faux-fur collar to dress it up for evening.

Stainless steel and very cool

Stainless steel tray, cup and spoon

I feel like if I were an architect at a chic Milan studio, this is how I would drink my coffee.

For more, read the best women’s shoes and boots for autumn and the expert guide to buying clothes that last

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