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 spring, 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 maxi to minidresses and lace-up to Western boots, keep scrolling to discover cool ways to wear ankle boots with dresses.
Styles Notes: The sun may be out, but the chill in the air hasn’t quite lifted yet. Thankfully, a sleek knit dress is the perfect antidote, and a pair of flat ankle boots will ground the delicate details of the knit dress.
This could pass for a treasured vintage piece.
This reversible coat gives you two looks in one.
You’ll wear these classic chelsea boots for years to come.
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.
All our editors have been eyeing up this leather blazer.
An everyday necklace.
This could easily pass for designer.
The Row’s chunky ankle boots are high up on my wish list.
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?
A seriously useful layering piece for these cooler months.
Sleek and chic.
Platform styles are extra comfortable.
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? Eni’s flawless example of blending her boots to the beige hue of her dress.
This lightweight fabric will work all year round, just layer up as need for autumn.
A best-selling design.
Beige and brown is such a timeless combination.
Style Notes: Ellie knows the power of flat ankle boots. For those dresses that we tend to dress up with heels, why not shake up your outfit rotations by grounding them with a flat ankle boot?
Make the most of your favourite dresses by styling for day and night.
This sculptural bag ticks all the boxes.
A staple pair of boots.
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.
This sleek shirt dress can be worn all year round.
Time to unpack your basket bags.
Cowboy boots are everywhere right now.
Style Notes: When it comes to choosing colourways, but don’t overlook the power of classics. A monochromatic look can be just as impactful as bold colours. Take note from Ada and go full force with accessories, boots and dress in harmonious hues.
One for the minimalists.
This versatile bag has gone viral for how much it can hold.
The chunkier, the better.
Style Notes: Give any dress instant edge by styling it with Western boots. Brittany Bathgate ensures her ensemble stays chic by sticking to a monochromatic colour palette.
A classic style for free time or office days.
A ’90s dream.
Inspired by classic western styles.
Style Notes: Floral dresses are a year-round staple, but come spring, they look their best worn with chunky, no-fuss flat boots, which provide a stylish contrast against the pretty print.
There’s so much to love about this dress.
The raw finish adds something special.
An all-weather shoe.
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.
This black and white version can be styled for day or evening.
A classic signet style ring is the perfect finishing touch to any outfit.
That’s right, sock boots are back in style.
This post was originally posted at an earlier time and has since been updated.
