What to wear in September: the perfect outfits for the most unpredictable month of the year

There’s a very particular buzz that characterises the month of September: the return to work, to commitments and to everyday life; the days getting shorter – though you really start to notice it; and the weather, which brings the lingering traces of summer and the first hints of autumn. All this is accompanied by a single question: what should I wear in September?

In the morning the air is already a bit cooler; during the day the temperatures still feel like summer; and in the evening that breeze arrives right on cue, making you regret going out without a jacket. Not to mention office outfits: is it already time to wrap up, or can we still be a bit more flexible? The solution is to play around with transitional pieces, continuing to wear some summer items whilst gradually adding more autumnal elements.

But if you’re feeling a bit lost and have no idea how to reorganise your wardrobe for September, don’t worry: in this guide, you’ll find plenty of outfit ideas perfect for the most unpredictable month of the year.

Back to work: light trousers and a shirt

After weeks spent in cool outfits and holiday looks, going back to work calls for slightly more formal attire, without sacrificing a light, airy feel. A pair of flowing or tailored trousers are the perfect base for getting back into the swing of things in style. Simply pair them with a white, light blue or striped shirt, worn loose or tucked into your trousers. On your feet, opt for light loafers, ballet flats or slingbacks.

Long dresses and skirts for leisure and walks

If September still brings warm days, there’s no reason to put your summer dresses away. A midi or long dress can be worn exactly as you would in August, simply by changing a few accessories. Instead of a straw bag, you could choose a leather one, whilst on your feet you can alternate between sandals, ballet flats or trainers.

Skirts are still perfect too: a flowing midi skirt with a T-shirt or a tank top makes for a simple, fresh outfit, but one that’s already more suited to the city than the classic holiday look. Of course, don’t forget to take a jacket with you for the evening or for cooler days.

A blazer over a dress: the perfect solution for evenings out

It’s one of the most successful combinations of the season, suitable for any occasion, from pre-dinner drinks to dinner itself, right through to a night out. A soft, lightweight blazer is perfect for pairing with a summer dress as we navigate this transitional period.

Jeans and a light top: the go-to look for September

Jeans naturally take centre stage again as the holidays draw to a close. But even here, it’s best not to make the look feel too autumnal straight away. A loose-fitting or wide-leg style can be paired with a T-shirt, a tank top or a light shirt, worn loose or tied at the waist. To complete the look, trainers and ballet flats work well during the day, whilst a pair of slingbacks or loafers make foran effortless outfit for evenings out.

For the weekend: midi skirt, T-shirt and denim jacket

Whether you’re planning a weekend away or staying in town, splitting your time between pre-dinner drinks and a spot of shopping in the city centre, a midi skirt, a T-shirt and a denim jacket are all you need. An easy, quick and comfortable combination that’s a real go-to: simply pair it with trainers or ballet flats for maximum practicality, or a pair of heeled ankle boots to add a touch of glamour.

Still undecided about your September looks? Take a look at our selection, which you’ll find at the end of this article, and let yourself be inspired.