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

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 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-126647-1695834889426-main

(Image credit: @frannyfyne)

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.

Shop the look:

2. Smock Dress + Chunky Chelsea Boots

ankle-boots-with-dresses-126647-1695834865756-main

(Image credit: @emmarosestyle)

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:

3. Striped Knitted Jumper + Sock Boots

ankle-boots-with-dresses-126647-1695834859378-main

(Image credit: @bubblyaquarius)

Styles Notes:  A sleek knit dress is a go-to for chillier spring days and a pair of heeled ankle boots is the perfect accompaniment.

Shop the look:

4. Slouched Blazer + Black Midi + Zip Front Boots

ankle-boots-with-dresses-126647-1695834853279-main

(Image credit: @_loissterling)

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:

This post was originally posted at an earlier time and has since been updated.

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over twelve years of experience in fashion journalism. She been creating engaging and elevated style content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories, and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, works closely with influencer talent on content initiatives, represents the brand at industry events, and regularly contributes to social media. Previously, Maxine appeared on TV in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o. 


Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship, she was offered a position on the Look magazine fashion desk. She accepted, leaving university a year early in the process. She went on to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion writer along the way. She later served as Look’s acting Editor in Chief before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others. Maxine works remotely from her countryside home near Edinburgh.