Like the childhood horror of going back to school after the summer holidays, returning to your office job after two weeks of sunning yourself (or more, if you’re one of the chosen few who managed to wrangle the whole of August off) can be a traumatic experience. It’s not just the thought of having to work that fills us with dread, but the darkening skies and cold evening commute, too. Not only do you have to adjust your mindset, but your entire wardrobe must accommodate the changing of the seasons. But, this is where the silver lining comes in: new clothes. Remember, though, that this is business and not pleasure. So, to ensure you don’t stray (too) far from the brief, we’ve devised a five-point plan that’ll whip your work wardrobe into shape. Let’s get started.

Like processing paperwork and learning how to correctly format a spreadsheet, stocking up on the basics – socks, shirts, underwear and so on – might be a tedious task, but it’s worth your while. After all, these are the foundations upon which great outfits are built. We’d advise investing in some workaday essentials: a store of plain white tees to wear under shirts or keep in your desk (à la Don Draper) in case of any lunchtime mishaps, an array of socks and, yes, some fresh underwear. That last item on the list will largely depend on personal preference, but if you’re in the habit of wearing tailoring to the office, boxer briefs are your best bet – Hamilton and Hare’s pairs are designed without seams using a tubular knit so they won’t bunch under fine fabrics.

This is the part where we talk about the weather. (We are British, after all.) Granted, you might not require a coat each and every day, but you will have to get used to routinely checking the forecast before your commute. Looks like rain? A clean-cut mac in navy or black that can be both dressed up or down is an adaptable addition to your arsenal. Clear skies? Go classic with a traditional camel overcoat – widely considered to be one of the most versatile outerwear options – or a tad less formal with a heritage check or fabric, such as this houndstooth coat from Officine Generale. The best part is any of these options will work well on a weekend outing, too.

As workplace dress codes have eased, so too has our definition of the word “smart”. What passes for dressed up or dressed down in your place of business will depend largely on several variables – the most important of which is your actual day-to-day duties; in some cases, the rules may even vary by department. It’s why, in 2009, the then-vice president of global human resources at General Motors, Ms Mary Barra (she became the CEO in 2014), replaced the company’s 10-page policy with just two words: “dress appropriately”. You already know what passes muster in your office, so if sweatpants fly, by all means, wear your most comfortable pair, but it will pay to make a little extra effort than usual during your first few weeks back. If you usually wear just a shirt, for instance, add an unstructured blazer on top. On the other hand, if you’re already accustomed to wearing a jacket, try stepping it up a notch with a proper two-piece suit.

While we’re on the subject of workplace formality, you can separate most modern offices into two categories: those where it’s entirely acceptable to wear sneakers, and those where it’s categorically not. If yours falls into the former bracket, it’s preferable to still err on the side of caution and go for something smart-ish, such as John Lobb’s considered cap-toed pair. For those in the latter camp with stricter parameters, these Edward Green Derby shoes are especially autumn-appropriate as they’re fitted with Dainite soles, which provide a touch more comfort than traditional hard soles and are well equipped to deal with wet weather. No matter how practical, however, nobody wants to wear their freshly polished work shoes on the train. At best, they’ll get grubby before you even set foot in the office; at worst, you’ll ruin them when you chance upon a particularly deep puddle. Instead, pack them in your bag (more on that below) and wear your running shoes on your commute. This is also an especially useful and space-saving tactic if you plan on squeezing in an early morning gym session, or just want to look like you have…

You’re a busy man: you’ve got places to be and many important things to do. With this fact of life comes the need to carry an assortment of items around with you. Shoving everything into your pockets simply won’t cut it. Besides, even the most generously pocketed pair of cargo trousers isn’t roomy enough to contain your gym kit, laptop, tablet (and their chargers), headphones, wallet, keys and other daily essentials. As a general rule, then, you’ll want to equip yourself with something on the large side: both TOM FORD’s Buckley backpack and Berluti’s polished Profil briefcase fulfil the capacity requirements. Be sure to slot in a slim portfolio (a piece that instantly makes you appear even busier and more important, we might add) that can accompany you to meetings and lunches without weighing you down.