Anyone still floating around with a straw basket and sandals may want to take note of the date. With September fast approaching, now is the time to forward-plan your wardrobe – or at least make the transition from clothes for ice-creams and picnics to ones for walks in woods and drinking red wine. Looking at autumn previews in magazines everywhere, you may already have started making the seasonal switchover. We certainly have. Here are seven questions – and answers – to help you switch seasons like a pro.

1. What one item will get me through the whole autumn/winter season?

Introducing the statement skirt. You may have one of these in your wardrobe already, but I bet it’s a bit jazz hands – fit and flare, or sequinned, maybe – compared with the wrap skirt. It has a very now, lackadaisical take on style. Already worn by Selena Gomez and Rihanna, I predict this will be a uniform for fashion editors at the shows this September – Gap does a great mid-length version. The slip skirt trend, kickstarted by the long-sold-out Realisation Par leopard-print one, hasn’t reached its peak on the high street yet but set a Google alert now. An item that looks great with a shirt and trainers or a jumper and boots is worth waiting for.

2. Which coat should I wear when it isn’t cold yet?

You know that trench that you bought last year? Get it out again. The trench coat was brought on to the catwalk by Céline, Vetements and, of course, Burberry in 2017, but it seems it is one of those trends that fashion ekes out. This is a bonus because, really, there is nothing better for this time of year when it is still too warm for a proper coat. If you didn’t buy one last year, the high street is your oyster – trench coats abound from Debenhams to M&S. Just in case you are over the trench coat, there’s the unfortunately named shacket, or shirt-jacket. Find it at Topshop.

3. Which boots should I buy?

Proper cowboy boots were a big thing on the catwalk – but the high street has helpfully realised that no one really wants to be Clint Eastwood on their daily commute. This autumn, go for the demi-cowboy, which hit just above your ankle bone and come with a chunky heel. Good for walking all day, good with jeans, I like this white pair currently on sale at Office. Also acceptable are knee-high boots, but not the kind everyone wore for going out-out circa 1998. These are either cone-heeled and slouched or wide on the leg, for Lauren Hutton vibes.

4. Should I really wear neon?

The short answer is yes. But if you have seen a picture of Kim Kardashian in head-to-toe highlighter yellow, don’t worry. You could dip a toe into the trend with a top to wear with jeans (neon looks great with denim) or an accessory. Weekday does a sweatshirt in highlighter yellow. There’s a neon Comme des Garçons wallet, which is a classic – and you can keep it in your bag if it’s not a bright kind of day. Nail colour is also an option; I like bright pink best.

5. Where are we at with sleeves?

Extreme sleeves – the kind that prevent you eating soup – are on their way out. But sleeves are still a thing. Autumn brings a slightly more sensible option: the long-sleeved shirt dress – Zara does one that manages to be both whimsical and edgy. Rather than the typical SFW examples, sleeves this season have a little bit of romance about them. See versions gathered at the wrist like a folky blouse, or scarf print on an oversized cuff. The new sleeve is wearable, a bit interesting and has little to no impact on your eating options – a trend we can get behind.

6. What should I put on my head?

Velvet headband, £28, Free People.

Heads are huge for autumn. Not literally, obviously, but fashion is big into headgear. The most extreme end of this trend is the balaclava – on the catwalk at Calvin Klein and Richard Quinn, and probably best left there unless you are planning a trip somewhere subzero. Instead, your options before we get to beanie weather include the baseball cap (Ralph Lauren Polo is a favoured brand of millennials) and the velvet headband (try Free People’s velvet option). Yes, the Sloane ranger favourite. Piecrust collar optional.

7. Is brown the new navy blue?

For anyone wedded to the fashionable yet understated power of navy, there is good news and bad news. Brown – which had a rep for drabness in fashion – is on the rise. This is partly due to fashion’s enduring crush on all things 70s. Brown clothes in 2018 are often also cord, an Insta-friendly way directly to the decade that taste forgot. Find yours at Monki and New Look. And the good news? Brown actually looks great teamed with navy.

This article contains affiliate links, which means we may earn a small commission if a reader clicks through and makes a purchase. All our journalism is independent and is in no way influenced by any advertiser or commercial initiative. By clicking on an affiliate link, you accept that third-party cookies will be set. More information.