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. As temperatures have swiftly plummeted, 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 winter 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: ’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: Jessie knows the easiest way to make vintage-inspired florals feel modern is with a pair of patent boots—particularly in a rich toffee hue. 

Style Notes: Eni knows that the perfect antidote to her twee bouclé dress is a pair of chunky flat boots. Nicholas Kirkwood’s faux-pearl numbers are too gorgeous to resist. 

Style Notes: Wrap dresses are unapologetically elegant, so we recommend playing on the elegant vibe with a pair of Victoriana-inspired lace-up boots just like María Bernad’s.



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: No one can give after-dark pieces a cool spin quite like Lucy, and this slip-dress–and–hiker-boot combination is certainly no exception. Bravo.

Style Notes: We often find that an unexpected accessory is the making of any great occasion outfit. Why not take a leaf out of Aimee’s book and wear your prettiest maxi dress with a pair of directional metallic boots in lieu of court shoes or sexy sandals?

Style Notes: When wearing powdery hues, make like Liv and play to the soft colour palette with white ankle boots. If that seems too stark for your liking, look for ecru shades or beige tones.

Style Notes: Avid readers of Who What Wear UK will know that we’re big fans of print clashing, and that extends to the dress-and–ankle-boot interpretations of the trend. Pair check or snake motifs with a printed dress in a similar vein. 

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

Opening Image: @wethepeoplestyle

Now, see the “boring” winter staple which is now the chicest thing you can wear.

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