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.
Shop the look:
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.
Shop the look:
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.
-
Dua Lipa Just Wore the Specific Boot Trend That Brings Boring Black Trousers Back to LifeA wardrobe-altering shoe.
-
I'm Calling It: These Classic Flats Are Set to Be the Most Stylish Shoes of 2025 (and Kendall and Hailey Agree)They make jeans look so elegant.
-
I Spent Hours Trying On Loafers—These 3 High-Street Styles Are the Best I FoundSophisticated and affordable.
-
Of All the Jeans I've Tried On, I Always Come Back to COS's Best StylesFit and sizing guidance included.
-
My In-Between-Season Wardrobe Is Getting a Little Boring—5 Legging-and-Boot Outfits I'm Hoping Will Change ThatPlenty of inspo ahead.
-
I've Been a Fashion Expert for 18 Years—Here's What I Rate This MonthRecommendations you won't find anywhere else.
-
Nothing Says "I've Got Great Taste" Quite Like Zara's Latest Drop of Designer-Looking BootsPut your best foot forward.
-
I Just Tried On the High Street Brown Suede Loafers That Will Sell Out NextTimeless and sleek? I'm sold.
