I Looked Through Thousands of Dresses and Boots to Find the 24 Best Ones

Yes, it's happening: Colder weather is here—thus it's time to do the big shoe switch. I've spent the whole summer trying out any sandals I can get my hands on. I even ditched my usual mules or strappy pairs for chunky Spice Girl–esque styles and accidentally (with no regrets, FYI) fell in love with Teva sandals. However, I'm willing to now give them all up in favour of fresh new-season boots. That said, I'm not willing to stick to a jeans-and-trousers–only wardrobe from here on out. Instead, I'm all about teaming my favourite summer dresses or new autumn frocks with boots. I'm not the only one either—some of my favourite Instagram girls have been opting to do the same.

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(Image credit: @ada_oguntodu)

Ada styles Nasty Gal toe-cap boots with a white midi dress.

From midi dresses and Western-style ankle boots to puffy dresses and hiker boots, there are so many ways to create winning combinations. 

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(Image credit: @slipintostyle)

Ellie brings a dressier Stine Goya dress straight into daytime territory with chunky boots.

You don't have to ditch your minidresses either, update them by teaming with knee-high boots to make them autumn-appropriate.

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(Image credit: @darjabarranik)

Darja shows how a double leather hit is the perfect new-season pairing. 

Scroll down to see and shop 12 dress and boot combinations you'll want to mix and match.

Shop Dresses With Boots

Related: These 3 Pairs of High-Street Ankle Boots Are Selling Like Crazy Already

Related: I'm Convinced That Everyone Looks Rich in This Autumn Dress Trend

Next up, this is the dress trend you'll wear on repeat for autumn/winter.

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Freelance Fashion Editor

Harriet Davey is a freelance fashion editor who has been part of Who What Wear's extended team since 2017. She previously worked in print at Look magazine and has since worked across print, digital and social for many other titles, including British Vogue, Stylist, Grazia, Refinery29 and Marie Claire. Also a stylist, Harriet has had the pleasure of producing cover shoots and editorials along with commercial shoots for brands including Boux Avenue, Watches of Switzerland, Benefit Cosmetics and Revolution. To add to this, Harriet also works in live TV styling for ITV’s This Morning. Back to Who What Wear. With hundreds of published stories on site, Harriet knows what the WWW reader wants. Keeping up to date with the latest It buys and runway trends, she can guarantee to keep you one step ahead of the most stylish people. When not writing or styling, Harriet loves to go shopping (yes, more fashion). If she’s not in a local Hackney bar or restaurant, you can find her forever searching for her next holiday destination.