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


(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.

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2. Smock Dress + Chunky Chelsea Boots


(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? 

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3. Striped Knitted Jumper + Sock Boots


(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.

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4. Slouched Blazer + Black Midi + Zip Front Boots


(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.

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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 thirteen years of experience in fashion journalism. She been creating engaging and elevated style content specifically 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, leads the editorial team in their SEO strategy and keyword planning, works closely with the beauty team on content initiatives, represents the brand at industry events, and regularly contributes to social media, including her own Who What Wear UK TikTok franchise, French Style Fridays. Previously, Maxine appeared on ITV's This Morning 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 at Look magazine, she was offered a position on the brand's fashion desk. She accepted, leaving university a year early in the process. Her passion and natural talent for writing and styling meant she swiftly rose through the ranks to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion and beauty writer along the way. She later served as Look’s acting Editor in Chief, overseeing both print and digital, before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others.

Maxine is based remotely from her countryside home near Edinburgh where she spends her downtime renovating her house, walking her dogs, hosting friends and trying to master the art of making Old Fashioned cocktails.