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How the Chicest Celebs Are Wearing Dresses and Boots This Autumn

by Maxine Eggenberger –

With the biggest designers lining around the block to dress them, it’s little wonder celebrities constantly provide us with outfit inspiration. The red carpet is all well and good (who doesn’t love a frothy Giambattista Valli gown?), but in our opinion, we see some of our favourite A-list outfits when they’re off out for dinner, at fashion shows or even running errands in downtown New York. And right now, it seems the stars are defaulting to the same autumnal outfit we ourselves are wearing on repeat: dresses and boots.

In an attempt to make the most of this in-between season—before the weather gets too cold to even entertain the idea of going bare-legged—we’ve been sporting dresses and boots nonstop. However, with mini, midi and maxi-length dresses to choose from—as well as ankle, calf, knee-high and over-the-knee boot options at our disposal—deciding upon a suitable pairing isn’t easy. Which is exactly why we’ve turned to celebrities. From Kaia Gerber and Elsa Hosk to Julianne Moore and SJP, as well as Katie Holmes keep scrolling to see the celebrities are wearing dresses and boots this autumn.

Oh, Katie. How we’re loving this new style direction for you. The classic silver bias-cut dress is super elegant, but those boots just add a touch of sass to make the whole outfit feel directional. Spot on. 

A great way to make a dress feel more grown-up is to add a pair of knee-high boots. Selena has nailed this look completely. 

Meghan pretty much always gets it right in our books. Here, she’s opted for a pair of classic black boots with her black dress. Chic and sophisticated. 

There’s something about this look that feels very un-Gigi Hadid, but we’re here for it. The green dress feels very festive and the boots make it feel even more so. One we’ll be copying for our festive parties. 

Rosie gives her slinky velvet dress a cool spin with the addition of black leather ankle boots.

We can always rely on Kate Bosworth to give her ensembles a unique twist, as this combination of a floral H&M dress and studded biker boots proves.

Alexa Chung wore a floral shirtdress and cowboy boots, so we wore a floral shirtdress and cowboy boots. 

Make like Tracee Ellis Ross and match the hue of your dress to that of your boots for a seamless ensemble. 

Poppy Jamie looks incredibly chic in this combination of a pink jacquard midi and black sock boots, which she wore to an Alexa Chung–hosted party last Christmas. 

Thanks to Victoria, we’ll all be coordinating our bots with an accent roll-neck worn underneath a printed dress this autumn. 

Always the fan of a print clash, we love how SJP has neutralised her checked coat and dress with a pair of grey knee-high boots. 

Emily Ratajkowski ups the ante of her simple back dress with a pair of bright snake-print boots. Inspired. 

Rochelle Humes won us over with her style this season with this Topshop daisy dress–and–patent boots look. 

Busy Phillips’s flash of pale leather boots underneath her Doên dress was a pleasant surprise.

All hail Katie Holmes’s recent style metamorphosis, which includes this incredible yellow floral maxi and lace boots. 

A puff-hem skirt is hard to pull off, but Julianne Moore does so with aplomb thanks to her pointed to ankle boots. 

Allow a bright dress to be the main focus of your look by wearing it with a pair of taupe boots, just like Olivia Palermo. 

Blue suede boots and a graphic brown and camel dress? Does Sienna ever get it wrong? (The answer you’re looking for is no.) 

Model Sam Rollinson expertly clashes her floral midi dress with a pair of on-trend snake-print ankle-grazers. 

Squint your eyes and you could easily be looking at a photograph of Kaia Gerber’s mum, Cindy Crawford, from the ’90s. Velvet on velvet? We’re here for it. 

Only Rihanna could leave us wanting to wear a split-hem, leopard-print dress with red over-the-knee boots. 

Even Priyanka Chopra wasn’t able to resist the allure of cowboy boots this season. 

Queen of the dress-and-boots combination is undoubtedly Anna Wintour, who has worn the failsafe duo for decades. 

Metallic boots and polka dots make for a fresh outfit pairing, as evidenced by Pixie Lott. 

Leomie Anderson’s lumberjack checks were made to be worn with hiking boots. 

This duo of a berry striped knitted dress and purple slouchy boots is as close to perfection as you can get. Bravo, Zendaya. 

Checked boots are hard to come by, but when you do, you’ll want to wear them with a bright colour-block dress like Adwoa Aboah. 

Been the colour of your dress to your boots like Margot Robbie for a fast-track to chic. 

Elsa Hosk was our go-to for summer outfit inspiration, and as this combat-boot–and–black-T-shirt-dress prove, it looks like she’s going to be an excellent source for autumnal style, too. 

Next: Our Editors Think These 4 Boots Go With Every Dress They Own

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