Posted on: December 28, 2023 Posted by: Comments: 0

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 year, 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.

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? Franny’s flawless example of blending her boots to the brown hue of her dress.

A classic piece you can wear to work and drinks.

For those bliss sunny autumn days.

This bag could easily pass for designer.

So ageless.

Style Notes: Emma knows the power of chunky ankle boots. For those dresses we tend to dress up with heels, why not shake up your outfit rotations by grounding them with an androgynous ankle boot? 

A classic style for free time or office days. 

A classic everyday bag.

These are great quality!

An every weather boot.

Styles Notes:  A sleek knit dress is the perfect piece for the upcoming seasons and a pair of heeled ankle boots will ground the delicate details of the knit dress. 

You’ll pull this striped knit out every autumn.

To polish off the look!

This bag is truly timeless.

That’s right, sock boots are always in style. 

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.

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.

Next up, It’s My Job to Find Amazing Shopping Picks—These 9 New Buys Are Too Good to Miss

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