9 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. Surely, I’m not the only one? This is precisely why I've set myself a bit of a style challenge—one I’m inviting you to join in too.

Since autumn has well and truly arrived, I’ve made it my mission to forgo denim for the foreseeable future (until it snows, at the very least), and instead, I’m going to embrace my favourite look of them all: dresses with ankle boots.

Dresses and ankle boots never fail to look chic and will help you navigate any and every sartorial hurdle the season throws at you. I wear mine for work, dinners out, drinks with friends, on shopping trips—heck, just about anywhere that doesn’t call for something slightly fancier, like, say, weddings.

Now, you might be wondering which types of ankle boots go best with which styles of dresses. Don’t worry—I turned to a few of my fashionable friends to find the answer. From maxi to mini dresses and lace-up to Western boots, keep scrolling to discover cool ways to wear ankle boots with dresses.

IT BUYS, UNITE

Style Notes: No one can give this season’s most in-demand buys a cool spin quite like Lucy Williams can, and this knit-dress-and-zip-up-boot combination is certainly no exception. Bravo.

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

BLENDABLE BOOTS

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 Delphine's flawless example of blending her boots to the pink accent hue in her midi dress. 

DO THE HIGH/LOW

Ankle Boots with Dresses: Wear mini dresses with chunky flat boots

Photo:

@eniswardrobe

Style Notes: Eni knows that the perfect antidote to her elegant and twee bouclé dress is a pair of edgy chunky flat boots. This marriage of fashion opposites is nothing short of inspiring. 

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.

EMBRACE THE CLASH

Ankle Boots with Dresses:

Photo:

@nnennaechem

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

ELEVATED TREND PIECES

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

Style Notes: Floral dresses are a year-round staple, but come autumn, they look their best worn with chunky, no-fuss flat boots, which provide a stylish contrast against the pretty print. 

SLINKY PAIRING

Ankle Boots with Dresses: Pair this season’s trending mesh dress with equally fitted sock boots

Photo:

@allisonho

Style Notes: There are two types of dresses that are dominating this season: oversized smocks (as we’ve detailed above) and tight-fitting styles, often modelled in mesh fabric. Allison Ho showcases how to style the latter—with an equally fitted pair of suede sock boots.

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