Humaa Hussain
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
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.
Shop the look:
A classic piece you can wear to work and drinks.
Keeping things in the same colour palette..
Prints are so in for autumn/winter 2024.
So ageless.
2. Cashmere Dress + Platform Boots
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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A classic style for free time or office days.
A brown leather brown look so chic with this outfit.
The perfect cold weather addition.
The chunkier the better.
3. Striped Knitted Jumper + Sock Boots
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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You'll pull this striped knit out every time the temperature dips.
To polish off the look!
This bag is truly timeless.
That's right, sock boots are always in style.
4. Slouched Blazer + Black Midi + Zip Front Boots
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.
Shop the look:
There's so much to love about this dress.
A slouchy and directional design.
An editor favourite.
The Row's chunky ankle boots are high up on my wish list.
This post was originally posted at an earlier time and has since been updated.
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I'm Building an Elegant, Cosy Wardrobe—This Cashmere Knit Is Top of My Wish ListAnd it's from the high street.
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Not Ankle Boots—The Rich-Looking Shoe Trend That’s Quietly Taking Over for Autumn 2025They have outfit-transforming powers.
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I Just Built an Expensive-Looking Capsule Wardrobe at Zara, H&M and COS—I've Outdone MyselfSo elegant, if I do say so myself.
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The One Boot Style I Buy Again and Again, Plus, My New Go-To Easy, Smart OutfitInvestment buys you won’t regret.
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I've Waited for Weeks—Finally, COS's Chic Cashmere Cardigan Is Back In StockAnd in three new shades.
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Don't Let Ankle Boots Have All the Fun—Personally, I Find This Autumn Boot Trend Even ChicerA wardrobe-altering buy.
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Not a Boot, Not a Loafer—This Is the Polished Shoe In-the-Know Fashion People Are Wearing Right NowAs timeless as they come.
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These 2 Simple Pieces Are the Key to One of the Most Classic Outfit Combos EverI bet they're in your wardrobe right now.
