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It’s a difficult time of year to pick what to wear. The weather is playing tricks on us: the morning will feel brisk and chilly; come lunchtime, you’re sweating through your sleeves, cursing your decisions and your body’s propensity for sweat patches.
Meanwhile, summer clothes have yet to be stored away; those flimsy blouses and smocks are looking at you seductively, edging you into taking a sartorial risk. And the sorry sight of your stacked jumpers, which have been hidden away for months, is too much to bear – it’s easier to ignore them for a little longer, to live in seasonal denial.
All this means that at this point, most of us are either too hot, too cold, or too aggravated to care. But regardless of any lingering uncertainty making us deeply indecisive about our outfits, we must still put clothes on. Thankfully, this is one of the best times to refresh your wardrobe, either with new purchases or ones you might’ve forgotten about that have re-entered the trend cycle, an inevitable outcome in fashion’s ever-revolving life cycle.
Without further ado, here are our top seven picks you need to enter this new season with confidence. And the good news is you probably own a few of them already.
The boots

Everyone on the front row at London Fashion Week was either in a pair of square-toed flats or knee-highs just like these ones by Lili Curia. Laces are key, as is the low, block heel. Wave goodbye to any pointy, slouchy boots from the days of yore. Those have now been relegated to the “mumsy” pile. Your boots need to be structured, sharp, and ideally, witch-inspired.
The Isadora Tall boots at Lili Curia are the ultimate autumn staple with their signature white laces. But Miista has plenty of options, too: we love the Nelly style that has a football boot-inspired exterior, with laces on the front and back. These are not the kind of shoes you stash in a bag only to slip into when you arrive somewhere: these are comfortable shoes you can stomp around in all day. They’re versatile, too: show them off in knee-length kilts and midi dresses, or pare them back with barrel jeans, where they can peek out and elevate a more casual aesthetic.
The jacket

If it doesn’t have a funnel-neck, it isn’t worth wearing. All the cool girls are swanning around in jackets stretching up to their ears. The more height, the better. Think giraffe levels of neck coverage. We’ve spotted these jackets everywhere, from the M&S runway that featured long, wool jackets with sharp, square funnel necks, to the rails at COS, which currently has some deeply chic funnel-neck trench coats on offer.
Any colour works, though we’d suggest picking up a neutral shade alongside something a little brighter. Massimo Dutti has a cherry red funnel-neck bomber jacket that would inject some joy into any autumnal ensemble – though it is often sold out due to its popularity.
The standout shade

Autumn is wrongly associated with deep, murky tones: think forest greens, navy blues, and reds so dark that they almost look black. These are good colours to own for this time of year, but it’s important to weave them in with brighter, statement shades, too. Last year was all about cobalt blues and apple reds. This season, it’s time to invest in vibrant emerald greens, like this Ganni dress, which can be dressed down as shown here over a poloneck jumper, or dressed up and worn on its own as a gown.
There are plenty of pops of this shade of green across the high street, too, like at COS, which has some striking bright green cardigans on offer, or at & Other Stories, which has a wide range of collared emerald green shirts. Who said Wicked season was over?
The jeans

Skinny jeans made a, thankfully, brief comeback last year. Then it was back to Levi’s 501s that had a high waist and a flattering fit. Now, it’s over to low-rise, baggy fits. And the looser they are, the better. Barrel jeans are still kicking about, too (they had a moment in spring), but for those who really want to swagger into the season on trend, it’s time to find the loosest pair of jeans you can.
No barrel, just straight down, swinging from your hips. The key is to make sure they fit snugly around you at the top so they can hang comfortably without needing a belt; if you can’t find the right shape for you, try taking them to a tailor. It will be worth it.
The bag

The ultimate autumnal handbag is capacious and swings from your shoulder, ideally in a slouchy, insouciant manner. This deep crimson one from Reformation is one of our favourites, mostly because it’s big enough to fit your laptop alongside your gym gear. On top of that, it’s a versatile colour that will go with just about anything, making even the most simplistic of outfits look elevated and more put-together.
There are variations on the theme everywhere, from Massimo Dutti to Anthropologie. Just be sure not to overstuff your slouchy bag so much that it changes shape. Nothing is quite as uncool, or uncomfortable, as a misshapen shoulder bag you can barely hold.

It’s very easy to get autumnal knitwear wrong. Find the wrong fit, and you can look frumpy. Choose the wrong shade, and it could totally wash you out. Terracotta is a decent neutral tone, as demonstrated by this Rejina Pyo round-neck jumper, which can be worn with anything from a leather mini skirt to wide-leg tailored trousers, as seen here. You could also wear it over a high-neck Victorian-style white shirt, with collars and cuffs popping out. The frillier, the better.
It also works well for layering (a very good tactic for anyone with a tendency to sweat as they move around on public transport at this time of year, constantly going from hot to cold), as seen here with a silky brown jacket wrapped around the waist.
The skirt

Wave goodbye to slinky midi silky skirts that seem to have dominated our high street shops all summer. It’s time for substantial, utilitarian cargo-inspired silhouettes that take up more space and offer a little more leg room. We love this puff skirt from Miista, which comes with ties and pockets. It’s an evolution of the popular Damson Madder skirts that overtook the internet last summer, though those came in vibrant reds and yellows. This has a more gothic sensibility, which is perfect as we approach Halloween. Elsewhere, you can find ruched, asymmetric skirts with a similar silhouette at All Saints; ASOS and Free People also have their own bohemian takes on the trend, too, in khaki and beige.
These skirts can be worn with anything from a simple white vest top and black bra (very Charli XCX) to an off-shoulder slinky blouse that you can tuck in. They will also go very well with your lace-up knee-high boots. Bonus: they’re extremely comfortable, which is always something we need a little more of in our wardrobes.