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

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 now in autumn, 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.

1. Pleated Shirt Dress + Heeled Brown Boots

Ankle Boots with Dresses: @frannyfyne wears brown heeled boots



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.

This bag could easily pass for designer.

2. Smock Dress + Chunky Chelsea Boots

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? 

Shop the look:

A classic style for free time or office days. 

3. Striped Knitted Jumper + Sock Boots

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. 

Shop the look:

You'll pull this striped knit out every autumn.

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.

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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