The Most Stylish Dress-and-Boot Pairings To Try This Autumn

As much as I love them and wouldn't be able to get dressed on the regular without them, I'm getting sick and tired of wearing jeans day in and day out. Which is why I've set myself a bit of a style challenge. With autumn on the horizon, I've made it my mission to forgo denim for the foreseeable future (until it snows, at the very least), and instead, embrace my favourite look of them all: dresses with ankle boots.

So which types of ankle boots go best with which styles of dresses? I turned to a few of my favourite influencers to find the answer. From maxi and mini to lace-up and Western, keep scrolling to discover eleven cool ways to wear ankle boots with dresses.

Style Notes: No one can give wardrobe staples a cool spin quite like Lucy, and this knit-dress–and–zip-up-boot combination is certainly no exception. Bravo.

Style Notes: '70s-inspired styling is proving to be one of the season's biggest takeaways. Why not consider re-creating Alyssa's jumper dress, checked-shacket–and–platform-boot combination to channel the covetable retro vibe?

Style Notes: Everyone knows one of the easiest ways to look chic is to match the colour of your footwear to that of your outfit. Case in point? Ellie's flawless example of blending her boots to the pink accent hue in her midi dress. 

Style Notes: Eni knows that the perfect antidote to her twee bouclé dress is a pair of chunky flat boots. Gianvito Rossi's track sole Chelsea boots are too good to resist. 

Style Notes: Avid readers of Who What Wear UK will know that we're big fans of the smock dress, and Harriet Stewart makes a good case for the smock-dress-and-cowboy-boot combo for autumn. Just so dreamy.

Style Notes: Give any shirtdress instant edge by styling them with Western boots. Brittany Bathgate ensures her ensemble stays chic by sticking to a monochromatic colour palette. 

Style Notes: We often find that a bold print is the making of any great outfit. Why not take a leaf out of Nnenna's book and wear a statement maxi dress with a pair of directional chunky boots?

This post was originally posted at an earlier time and has since been updated.

Next Up, Autumn/Winter 2020 Trends: The New Fashion Looks You Need to Know

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