I think back to school and back to work provoke surprisingly similar emotions. Some people cannot wait for a fresh start, a new routine and that oddly satisfying feeling of getting organised again. Others would happily stay in summer mode indefinitely, pretending their inbox does not exist and keeping the to-do list as beautifully empty as possible.

Unfortunately, that is not really an option for schoolchildren – and even less so for the rest of us.

Back to work is just around the corner, and while I cannot make your first Monday morning any easier, I can at least make getting dressed for it slightly less complicated.

September workwear has its own set of challenges. It is still warm enough that a full autumn wardrobe feels premature, mornings are becoming noticeably cooler, offices seem to have their own completely independent climate, and there is always the possibility that a working day turns into dinner or drinks without enough time to go home and change.

So rather than thinking in terms of individual outfits, I prefer simple formulas: combinations that look polished, feel appropriate for work and can easily adapt to whatever the day has planned. Here are five worth keeping somewhere in the back of your mind this September.

Oversized blazer + white T-shirt or tank + tailored trousers + kitten heels or loafers + structured bag

There is a reason this combination keeps coming back. It looks polished without feeling overly corporate and, perhaps more importantly, requires almost no thought at 7:30 in the morning.

The trick is in the proportions. If the blazer is oversized, keep the layer underneath simple and relatively fitted, then choose trousers that fall beautifully rather than adding too much volume everywhere. A good leather belt and structured bag will do most of the remaining work.

The September trick: keep the blazer with you even if the morning is warm. Between aggressively air-conditioned offices, cooler evenings and spontaneous after-work plans, it will probably earn its place by 6pm.

Crisp shirt + straight-leg denim + belt + loafers or ballet flats + watch

For offices where denim is acceptable, this might be the easiest formula of them all. A great white or pale-blue shirt immediately makes jeans feel more intentional, while loafers and a leather belt bring everything together.

The important part here is choosing the right denim. Save distressed, very washed or overly casual jeans for the weekend and go for a clean straight-leg or slightly wide silhouette in a classic blue or darker wash.

And if your workplace leans more formal? Keep everything else exactly the same and simply swap the denim for tailored trousers. One change, completely different dress code.

Waistcoat + matching trousers + ballet flats + minimal accessories

Matching sets are essentially a cheat code for looking put together.

They give you the effect of a carefully considered outfit without actually requiring you to coordinate very much at all. A waistcoat and trousers still work beautifully during warmer September days, while a relaxed shirt-and-trouser set is perfect when you want something a little softer.

The best part is what happens afterwards. Wear the trousers with a white T-shirt and blazer, the waistcoat with jeans, or the shirt open over a tank. If you are shopping for workwear now, pieces that can create three or four outfits separately are always a smarter buy than something that only works one way.

Midi skirt + simple T-shirt or fine knit + blazer + kitten heels

A skirt does not automatically have to mean pencil skirt, white shirt and pumps. In fact, I think modern office dressing becomes much more interesting once we move away from those very literal combinations.

A fluid midi skirt with a simple T-shirt or fine knit feels feminine without being fussy, while a blazer gives it enough structure for work. Kitten heels are particularly useful here: polished enough for a meeting, realistic enough for an actual working day.

One small styling rule: if the skirt is the interesting part of the outfit — satin, pleated, printed or beautifully cut – let it be. Everything around it can stay incredibly simple.

Simple midi dress + leather bag + flats or loafers + cardigan

Possibly the best option for those mornings when deciding what goes with what feels like one decision too many.

A beautifully cut midi dress needs very little help: good shoes, a proper bag, perhaps a watch or simple jewellery, and you are done. Look for something that feels polished rather than occasion-specific, so it can work just as easily at 10am as it does at 7pm.

And this is where September dressing becomes slightly strategic. At 8am, grab the cardigan even if you do not think you need it. We are no longer in that part of summer when you can confidently assume it will still be 30 degrees after work. Leave it over your shoulders, in your bag or on the back of your office chair – you will be very pleased with yourself when dinner runs late and the temperature suddenly drops.

The easiest way to make September mornings less chaotic is not necessarily to buy more, but to make sure the pieces you already own actually work together.

A great blazer, crisp shirt, quality white T-shirt, tailored trousers, straight-leg jeans, midi skirt, simple dress, fine knit or cardigan, loafers and a structured everyday bag are enough to build almost everything above.

Think of them as your working wardrobe rather than individual purchases. If one new piece can work with at least three things you already own, it has a much better chance of becoming something you genuinely wear.

Getting back into work mode might take a little longer than getting back into work clothes. Luckily, the second one can be made considerably easier.

Below, I have put together some of my favourite pieces for recreating these formulas and making the transition into September feel a little more effortless.

READ MORE:

50 Midi Dresses I Am Loving Right Now

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