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6 Dress And Boot Combinations To Extend That Summer Feeling Into Autumn

Your favourite summer dress, plus new-season boots equals trans-seasonal styling, sorted.

By Natalie Hughes
summer dress autumn boot pairings
Valentina Valdinoci

Now that temperatures have dropped a little, I keep gazing wistfully at my autumn boots. Then again, I’m not quite ready to part from my beloved summer dresses. The good news is, you can have everything – well not everything, but, you know – since the simple formula of boots and a summer dress solves most between-season styling dilemmas, making the transition into autumn more effortless.

If you thought your halterneck mini was nothing without a pair of ballet flats, think again. Its Y2K-leaning sensibility makes it the perfect match for the slouchy boots that made an appearance on the AW25 runways, at Isabel Marant, Khaite and Louis Vuitton. Hold on to your satin slip dress, too – it makes an excellent layering piece when teamed with biker boots and a slouchy knit (and jeans, on extra chilly days).

It’s certainly not the cowboy boot’s first rodeo, as it stomps defiantly onwards into another season thanks to Altuzarra and Isabel Marant, who has long loved Western-inspired styling. Later, wear yours beneath sharply tailored trousers (as at Calvin Klein); now, slip ‘em on with a white cotton sundress for late summer festivals and hoedowns.

Whether you prefer an equestrian or Victoriana vibe, there is a new-season boot for you. Invest in your perfect pair and wear it right away, combining riding boots with a denim dress or lace-up styles with wafty, boho midis and maxis.

Without further ado, here are six tried-and-tested dress and boot pairings for a chicer almost-autumn.

A Boho Maxi Dress…

Rixo Raina Midi Dress

Raina Midi Dress
And Lace-Up Boots

Zara Leather Kitten Ankle Boots

Leather Kitten Ankle Boots

You’ve spent all of summer wafting around town in a Chloé-esque maxi and there’s no need to let autumn stop you – simply swap out your ballet flats or jelly shoes for a pair of lace-up boots, either Victorian-inspired (as seen at Bora Aksu’s AW25 show) or biker-style, seen at Dior.

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A Denim Dress…

Aligne Lucas Mini Denim Dress

Lucas Mini Denim Dress
And Riding Boots

Reformation Nancy Knee Boot

Nancy Knee Boot

For chillier, late-summer days, hedge your bets in a long-sleeved, A-line mini dress (in denim, depending on the temperature) and riding boots. ELLE UK’s Site Fashion Editor Daisy Murray wears the combo especially well.

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A White Cotton Sundress…

Peachy Den White Dylan Romper Dress

White Dylan Romper Dress
And Cowboy Boots

Isabel Marant Suede Cowboy Boots

Suede Cowboy Boots

Crisp cotton sundresses served you well all summer – continue the party into autumn by eschewing sandals for cowboy boots. Judging by Altuzarra and Calvin Klein’s AW25 shows, they’re not going anywhere.

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A Halterneck Mini Dress…

Zara Embroidered Halter Dress

Embroidered Halter Dress
And Slouchy Boots

Isabel Marant Edrik Gathered Leather Ankle Boots

Edrik Gathered Leather Ankle Boots

Last seen sometime in the early aughts, the slouchy boot was well overdue a second wind. Well, it’s back with a vengeance, thanks to Khaite, Zimmermann and Isabel Marant, whose Edrik boots are perfectly in-keeping with the Y2K look of a halterneck mini dress.

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A Satin Slip Dress…

Zara Pink Slip Dress

Pink Slip Dress
And Biker Boots

Miista Sigrid Black Tall Boots

Sigrid Black Tall Boots

Reward the satin slip dress’s unerring loyalty in a heatwave by styling it throughout September and into October, with knitwear and buckled boots – the chunkier, the better.

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A Drop-Waist Dress…

Gimaguas Joan Midi Dress

Joan Midi Dress
And Brown Boots

Paris Texas Anja Leather Knee Boots

Anja Leather Knee Boots

Brown boots ruled the runways at Khaite, Alberta Ferretti and Fendi (amongst others) and will be a key part of your winter wardrobe. For now, we love how they look with a flippy, drop-waist dress, like this ruffled Gimaguas number.

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