12 transitional dresses to buy now and wear into autumn, plus how to style them no matter the weather

12 transitional dresses to buy now and wear into autumn, plus how to style them no matter the weather

We like to get the most out of our wardrobes, so as the summer draws to a close, we’re only interested in shopping for transitional dresses. Meaning, summer dresses we can wear now *and* into autumn, with just a few smart style swaps.

The obvious being switching your sandals for closed-toe shoes such as loafers, ballet flats or boots. But not all dress styles suit trans-seasonal footwear. And no matter how hard you try, sometimes a multi-coloured floral print mini does just look out of place in October.

To help you shop smart, we’ve rounded up six of the best transitional dress trends – plus our top picks of the exact dresses worth shopping on the high street right now.

Everyone’s clicking on…

Denim dress

Aligne Amber Mini Denim Dress
Credit: Aligne

Denim Tunic

Arket Denim Tunic
Credit: Arket

Thanks to the heavyweight fabric, a denim dress will effortlessly see you from summer into autumn, requiring few styling substitutions in the process. Our favourite way to wear them is with one of our favourite transitional shoe trends – think fashion trainers, loafers and socks, or boat shoes. In time, this will become boots, be it biker or cowboy styles. Look for mini-length designs with sleeves to make the most of the lingering sunshine, and when the mercury truly drops, layer a roll-neck underneath for maximum warm layers.

Polka dot dress

Black Polka Dot Ruffle Lyndsey Midi Dress

Nobody’s Child Black Polka Dot Ruffle Lyndsey Midi Dress
Credit: Nobody’s Child

Ruched Polkadot Maxi Dress in Brown

Topshop Ruched Polkadot Maxi Dress in Brown
Credit: ASOS

Polka dots are still set to be big news in autumn, as seen on the AW25 runways at Altuzarra, Fendi and Brandon Maxwell. Brown polka dot patterns will feel really seasonal and give a refreshed take on the print, but black-backed versions are still totally acceptable. Again, look for short-sleeve styles and get ready to swap your sandals for boots. We’re also excited to wear a jumper over the top, belted in place, to create the illusion of a polka dot skirt.

Knit dress

Aiden Knit Dress

Reformation Aiden Knit Dress
Credit: Reformation

Perkins-Neck Knitted Dress

Mango Perkins-Neck Knitted Dress
Credit: Mango

Similar to denim, a knitted dress transitions well for autumn thanks to its fabrication. A thin-enough knit to work for now with bare legs and sandals, it looks just as good with boots (and tights too, when it gets really cold). Even knitted sleeveless styles, when paired with the right footwear, can work as late as December. Truly, few dresses are more versatile.

Tomato red dress

Saffy Midi Dress

Damson Madder Saffy Midi Dress

Now 25% Off

Credit: Damson Madder

Bryson Dress

Reformation Bryson Dress
Credit: Reformation

Pastel colourways are associated with spring and summer, while warmer, earthier tones belong to autumn as they evoke the feeling of the changing season. Shelving your butter yellow (*sob*) in favour of a new season colour trend is one way to instantly feel more autumnal. Enter: tomato red, per the AW25 runways at Altuzarra, Calvin Klein and Christopher John Rogers. Admittedly, not your typical autumn hue, but that’s exactly what makes it a great buy for now. Let your accessories – swap white for black, and sandals for boots – change the mood come September.

Midaxi dress

Grace Jersey Gingham Check V-Neck Maxi Dress

Hush Grace Jersey Gingham Check V-Neck Maxi Dress
Credit: Hush

Cornflower Blue Grace Dress

Never Fully Dressed Cornflower Blue Grace Dress
Credit: Never Fully Dressed

Regardless of print, fabric or colour, the easiest kind of transitional dress is a midaxi dress. Not only does the longer hemline keep your legs warm in the cooler weather of autumn, but it also guarantees you can wear your dress with boots (AKA our favourite autumnal footwear), as there’s less likely to be an awkward gap between the bottom of your dress and the top of your boots. No matter the boot style you opt for, ideally, you want your dress to finish below the tops of your boots.

Nightie dress

Nightie dresses have dominated summer dress trends and are set to stay for autumn. Good news if you’ve already invested, and giving you the perfect excuse to finally do so if you’ve so far been resisting. Look to the AW25 runways for styling inspo, where Cecilie Bahnsen and Blumarine offset the delicate sheer fabrics with socks and chunky trainers and knee-high boots, respectively. Similarly, Louis Vuitton relied on dark accessories to bring an autumnal mood, and Chloé skipped straight to winter, pairing lace negligees with faux fur coats.

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Headshot of Alexandria Dale

Alexandria Dale is the Digital Fashion Writer at Cosmopolitan UK. Covering everything from the celebrity style moments worth knowing about to the latest fashion news, there’s nothing she loves more than finding a high street dupe of a must-have designer item. As well as discovering new brands, she’s passionate about sustainable fashion and establishing the trends that are actually worth investing in. Having worked in fashion journalism for six years, she has experience at both digital and print publications including Glamour and Ok! 



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