4 Elevated Yet Easy Dress-and-Boot Pairings to Try This Autumn

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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.

As we're nearing the new season, I’ve made it my mission to forgo denim for the foreseeable future, 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, such as a wedding (of which I have a handful this year).

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 ribbed maxi to cashmere and chunky boots, keep scrolling to discover cool ways to wear ankle boots with dresses.

1. Ribbed Maxi Dress + Brown Suede Boots

_jeanettemadsen_

(Image credit: @_jeanettemadsen_)

Style Notes: A black ribbed maxi dress is sleek and versatile, but pairing it with brown suede ankle boots adds a warm, casual touch. The contrasting textures create balance, perfect for daytime wear. Keep accessories minimal—think gold jewellery or a simple crossbody bag.

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2. Cashmere Dress + Platform Boots

annabelrosendahl

(Image credit: @annabelrosendahl)

Style Notes: Pair a soft cashmere dress with chunky platform ankle boots for a modern, edgy contrast. The boots add boldness, while a neutral or monochrome palette keeps the look polished. Add a structured coat to complete the outfit.

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3. Striped Knitted Jumper + Sock Boots

ankle-boots-with-dresses-126647-1695834859378-main

(Image credit: @bubblyaquarius)

Styles Notes: A sleek knit dress is a go-to for chillier autumn days and a pair of heeled ankle boots is the perfect accompaniment.

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4. Slouched Blazer + Black Midi + Zip Front Boots

ankle-boots-with-dresses-126647-1695834853279-main

(Image credit: @_loissterling)

Style Notes: There are two types of dresses that are dominating this season: tight-fitting styles and oversized smocks. Lois showcases how to style the latter—with an equally fitted pair of zip boots.

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

Maxine Eggenberger
Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s Deputy Editor and has over fourteen years of experience in fashion journalism. She been creating engaging and authoritative content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, talent interviews self-styled shopping stories and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, leads the editorial team in their search and keyword planning, works closely with the fashion and beauty team on strategy and continues to pen many of her own articles. Prior to Who What Wear UK, Maxine's contributed to publications including Grazia, InStyle Marie Claire, Elle and Look, amongst others.

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