No sooner did September arrive than the autumn weather followed. Rain, wind and grey skies, and yet... still weirdly warm? Speaking for myself, I was nowhere near prepared for the drastic change from summer to autumn dressing. Curating an outfit for September weather is truly a science, but fear not, I am here to help you weather the storm (pun *definitely* intended). So, it's time to swap your sandals for loafers, and your tanks for trenches as you optimise your wardrobe for transitional dressing.

It's perfect timing too, with London Fashion Week in full swing, you need only look to the streets for some serious autumnal inspiration. My cute September outfit picks are actually from the New York Fashion Week street style, so there's something to suit every type of occasion.


An autumn colour scheme

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Girls will be like, "I need this," and it's just an all-brown outfit and a lavender latte. Fall is within sight, so dust off your favourite autumnal hues – starting with mocha shades favoured by Sabrina Carpenter and other celebs.

A button-down and jeans

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Allow me to introduce you to my emotional support outfit – the one I throw on when I'm feeling lazy and uninspired, but still want to feel cool and fashion editor-y. The equation is as follows: baggy jeans + perfectly-oversized graphic tee + bright striped button-down + a pile of mismatched necklaces.

A tent dress and trainers

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In the world of fashion, Ganni is never wrong. Channel their trademark look with a poofy dress and trainers when you need a casual-but-cute look that you can walk around in all day long.

An unexpected jumper moment

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On days when you're dying to dip into your jumper reserve but the weather just won't let you, I recommend tying one around your waist. Grab one in a contrasting colour to add to the eclectic vibe.

Everyone's clicking on...

A sheer tank and jeans

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Pivot your most summery tank top into almost-autumn territory with a pair of matching jeans to ease your way back into full-coverage dressing.

A rugby shirt and micro-mini

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The baggy shirt + micro skirt look is one that's gotten me through more than a few Saturday brunches. A rugby-style top adds to the trendy tennis-core vibes.

The first plaid dress of the season

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Few things hit harder than the first plaid of the season. But since the weather is still fairly mild, I'd opt for a little plaid dress in a lightweight fabric. Leopard print shoes will make the classic print feel undeniably fresh.

A breezy button-down and midi skirt

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Now's the time to shift from teeny-tiny skirts to midi and maxi. Try styling with a loose-fit button-up and loafers to make an A-line skirt feel more office-appropriate.

Short shorts and a long jacket

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Get a few more wears out of your shortest hemline by layering it under an ankle-length duster jacket for a bit of additional coverage. Go for knee-high boots rather than flats to balance out the cheeky cut.

A button-down and tracksuit

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Reunited and it feels so good! Finally, your beloved Adidas tracksuit can return to the fashion lexicon once more—and you won't be separated from it any time soon. Style them for work with a dress shirt and slingback kitten heels.

Headshot of Kelsey Stiegman

Kelsey (she/her) is a freelance digital fashion editor and writer with a knack for turning top-performing content into top-selling content. She has extensive experience in editorial and e-commerce strategy, having worked in both divisions during her years at Seventeen and Bustle. With more than a decade of experience in digital media, she also offers creative and social media consulting, as well as copywriting services. She enjoys cheeseburgers, traveling, and vintage hauls. Follow her on Instagram at @klstieg.