What boots are in style to wear with dresses?

August 31, 2022 - 17:09 BST Get a wardrobe inspiration boost with our favourite dress and boot combinations to wear this season

The end of August means one thing, and one thing only. Enter: the ever-tricky transitional dressing period. Bridging the gap between summer and autumn is a slippery beast to conquer – clinging onto the dregs of the warmer months by stepping out in your favourite dress is frustratingly thwarted by puddles and vicious gusts of wind.

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Open-toed shoes are a no-go, which presents the opportunity for you to raise your boot game. If, like Kendall Jenner, you're all about the Wild West look this autumn, you can't go wrong with a pair of silver cowboy boots by Annie's Ibiza x Terry de Havilland. Whereas if you're looking to up the ante with a splash of colour, Proenza Schouler does an excellent ankle boot in a vampy red.

Hello! Fashion shares the best dress and boot combinations to try this season:

The knitted dress and the cowboy boots

  Knitted-Dress-Cowboy-Boots

Am up a classic jumper dress by leaning into its base shade. The coolness of the lilac pairs perfectly with a futuristic-looking Jacquemus shoulder bag and lustrous cowboy boots.

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annies-ibiza-boots

Silver cowboy boot, £350,Annie's Ibiza

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The floaty dress and the cut-out heel boots

Floaty-Dress-Cut-Out-Heel-Boots

Bring structure to the forefront and style up a neutral loose-fit midi with a thick statement belt and black pointed boots with block-heel cut-out detailing.

  Victoria-Beckham-Cream-Dress

Wrap midi dress, £890,Victoria Beckham

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The polka dot dress and the riding boots

  Polka-Dot-Dress-Riding-Boots

Going back to basics has never looked more chic – the eternal polka dot print is kept light and modern in a high-necked waterfall design, paired with a quality leather riding boot.

  Jil-Sander-Riding-Boots

Jil Sander leather riding boots, £1,080,Mytheresa

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 The collared dress and the chunky boots

  Collared-Dress-Chunky-Boots

Fans of a minimalist moment need look no further than this off-white shift dress, beige no-lapel blazer and ultra-stompy platform boots.

Maje-Collared-Dress

Maje Rimisa asymmetric ribbed stretch knitted midi dress, £279,Selfridges

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The blazer dress and the knee-high boots

  Blazer-Dress-Boots

Sheer tights and knee-high boots simply ooze an effortless autumn style moment. With sharp tailoring and a severe V-neckline, a powerful blazer dress is at the top of our wish list this season.

  Mugler-Blazer-Dress

Mugler multi-strap padded-shoulder woven jacket, £1,740, Selfridges

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The off-the-shoulder dress and tan boots

  Off-The-Shoulder-Dress-Tan-Boots

Thigh-high boots are worth their weight in gold when it comes to making a footwear statement – pair with an asymmetric mini for maximum impact this season.

  Paris-Texas-Boots

Paris Texas Kiki over-the-knee leather boots, £675,Mytheresa

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The cut-out midi dress and patent ankle boots

  Cut-Out-Dress-Patent-Boots

A stylish black dress will always be in fashion – we love the subtleness of the cut-outs in conjunction with the drama of a patent red ankle boot.

  Proenza-Schouler-Boots

Proenza Schouler crinkle patent ankle boots, £630,Farfetch

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The striped mini dress and the statement boots

  Striped-Mini-Dress-Statement-Boots

Refresh your favourite summer mini dress by styling it with a printed shacket and vibrant round-toe boots, upping its versatility.

  Missoni-Stripe-Dress

Missoni zigzag-woven mini dress, £500,Farfetch

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What kind of boots look good with dresses?

Short boots, like ankle boots and Chelsea boots are perfect for wearing with dresses through every season, whether it be winter or summer. Ankle boots are perhaps the most popular style for wearing with dresses as their short silhouette will elongate the appearance of your leg.

Are ankle boots Still in Style 2022?

From subtle versions like the Sempre Di ruched ankle boot to more traditional ones like the Felmini cowboy boot, western-inspired ankle boots are a perfect long-term investment. They're never out of style and you can wear them with pretty much everything!

Are tall boots in style 2022?

Yes, classic knee-high boots are back, whether you prefer flat riding boots or '90s square-toe heels. Even knee-high moto boots are having a moment. The best way to wear them right now (so that you don't look too retro) is with skirts or dresses that hit above the knee rather than tucked in leggings or skinny jeans.

Is it fashionable to wear ankle boots with a dress?

Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you're rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.