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Knee-highs, cowboys and chunky-soled styles are all ready and waiting this season.

We’ve well and truly waved goodbye to summer, but it’s not all summertime sadness as Lana Del Ray would make out. In fact, when it comes to fashion, winter wardrobes may actually be our favourite, kicking sandals and linen shirts to the curb in favour of trusty leather trenches, collared knits and joyful jumpers.

Turning our attention to footwear, boot season has now begun. Although we love them as a year-round staple, autumn sees them really come into their own with waterproof wonders, knee-high heels and chunky-soled chelsea boots keeping us warm and toasty with a fashionable flair. 

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Compared to summer, comfort is now key, with the tumultuous weather adding a tricky twist to getting dressed each morning. Although we love a sultry suede ankle boot, you’ll be deflated if a downpour takes hold, so practicality also has to come into play. And just a quick peek at September’s fashion week street styles cement the boot as the best accessory for this time of year.

Paired with dresses, boots can toughen up a flirty floral frock and make minis more practical for the everyday grind. Lusty leopard print, pared-back black and vibrant white styles are in no short supply, and we’ve rounded up the best boots to buy now that will see you through winter and beyond. So, whether you’re after long or short, heeled or flat, bold or basic, look no further than our Stylist edit of the best autumn/winter boots to dress down or jazz up your dresses this season.

  • Aeyde Henry leather knee boots

    Best winter boots to wear with dresses: Aeyde Henry leather knee boots

    A classic riding boot will never go out of style. Whether you’re looking to channel the cavalry with matching jodhpurs and a white shirt or keep it nice and simple with a black midi dress, these Aeyde leather boots are sure to see you through many a winter gale.

    Shop Aeyde Henry leather knee boots at Net-a-Porter, £595

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  • Russell & Bromley company combat chelsea boot

    Best winter boots to wear with dresses: Russell & Bromley company combat chelsea boot

    Leopard print lovers rejoice as this one is for you. Whether you’re looking to jazz up a basic black maxi dress or clash colours with a vibrant orange mini, these chunky-soled chelsea boots are sure to keep it cool and casual with a fun, fashionable flair.

    Shop Russell & Bromley company combat chelsea boot, £325

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  • Ugg ultra mini classic boots

    Best winter boots to wear with dresses: Ugg ultra mini classic boots

    Whether you love them or hate them, Ugg season is upon us. Well and truly in the fan club of the cloud-like shoes, we’re wearing them with dresses, jeans, joggers and anything and everything we can for ultimate comfort no matter the occasion. OK, maybe we can’t quite wear them to the office, but we can dream.

    Shop Ugg ultra mini classic boots at Next, £135

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  • Charles & Keith Lula patent chunky heel calf boots

    Best winter boots to wear with dresses: Charles & Keith Lula patent chunky heel calf boots

    Like something from the future, these boots have really caught our eye. Made from faux patent leather, they’re definitely a funky fit with an abstract sole like we’ve never quite seen before.

    Shop Charles & Keith Lula patent chunky heel calf boots, £99

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  • Allsaints Reina leather crinkle boots

    Best winter boots to wear with dresses: Allsaints Reina leather crinkle boots

    Over-the-knee boots are one of the sexiest shoes around, and this gunmetal grey pair is no exception. With a slight heel, pointed toe and wide-leg design, they’re quite the standout style. Could kinky boots be calling your name?

    Shop Allsaints Reina leather crinkle boots, £349

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  • Sante+Wade jummai yellow boots

    Best winter boots to wear with dresses: Sante+Wade jummai yellow boots

    Just as leopard print is rising again in the style stakes, snake print isn’t too far behind. Yellow in colour, this Sante+Wade pair is on the loud side, but pairs perfectly with black, brown or autumnal hues for a real style statement.

    Shop Sante+Wade jummai yellow boots, £250

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  • Ted Baker Mosie faux shearling hiker boots

    Best winter boots to wear with dresses: Ted Baker Mosie faux shearling hiker boots

    Shearling season is upon us, and boots are one of the easiest ways to jump on the trend. In a classic biker style, this lace-up pair just screams warmth. While the shearling tongue is faux, the boots are made from a soft yet sturdy leather and are sure to see you through many a winter in style.

    Shop Ted Baker Mosie faux shearling hiker boots, £175

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  • Ariat Delilah round toe waterproof western boot

    Best winter boots to wear with dresses: Ariat Delilah round toe waterproof western boot

    Home to the humble cowboy boot – yes, they’re back for autumn, they never really left – Ariat boots are somewhat famous in the cowboy-loving crowd. Waterproof, these are a great choice whatever the weather, while the brown colourway is sure to look beautiful with any midi or mini dress.

    Shop Ariat Delilah round toe waterproof western boot, £145

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  • Hush Tallis leather boots

    Best winter boots to wear with dresses: Hush Tallis leather boots

    Although white may not win on a practicality side, this pair is perfect to pair with any dress – so long as you look at the weather first. A mid heel adds height while the pointed toe elongates the leg, meaning maxis, midis and minis are all on the cards.

    Shop Hush Tallis leather boots, £169

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  • Merry People Bobbi wellington boot

    Best winter boots to wear with dresses: Merry People Bobbi wellington boot

    Waterproof boots aren’t always fashionable. While we love a good pair of wellies, you can’t necessarily wear them to the office with pride, until now. Merry People’s waterproof boots are sure to work wonders come rain or shine, and they’re rather sweet-looking too.

    Shop Merry People Bobbi wellington boot, £79.95

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  • Paris Texas 65mm croc-embossed leather boots

    Best winter boots to wear with dresses: Paris Texas 65mm croc-embossed leather boots

    Mock-croc accessories are only growing in popularity, so it’s no surprise boot brand extraordinaire Paris Texas is packing a punch with this knee-high option. Working with everything from minis to maxis, they’re sure to elevate any look in height and in style.

    Shop Paris Texas 65mm croc-embossed leather boots at Farfetch, £565

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Images: Courtesy of brands.

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