Celebrity
Jan 20, 2020

How the Chicest Celebs Are Wearing Dresses and Boots Right Now

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—while the weather is still cold but the days are gradually getting brighter—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 right now.

Celebrities Wearing Boots and Dresses: Katie Holmes wearing a silver dress and boots

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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.

Celebrities Wearing Boots and Dresses: Selena Gomez in a pattered dress and black boots

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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.

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We had no idea that Kylie Jenner shopped at COS until she posted this snap. We love how she's styled her casual knitted with with a pair of on-trend hiking boots.

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Yellow suede boots may sound daunting to wear, but Cynthia pulls them off like it's no big deal with a printed Zimmerman dress.

Celebrities Wearing Boots and Dresses: Laura Dern wears a polkadot dress with black ankle boots

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Polka dots are set to make a triumphant return this year and, of course, Laura Dern is already in on the action. Note how she gives the retro motif a very modern feel by styling it with minimal black leather boots.

Celebrities Wearing Boots and Dresses: Jenna Coleman wears a purple printed dress with black patent boots

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Jenna Coleman's dress collection is a thing of beauty, and this purple floorsweeper is no exception. While it wouldn't look out of place on the red carpet, Jenna downplays to with the addition of patent block-heel boots.

Celebrities Wearing Boots and Dresses: Yara Shahidi gives her black chiffon dress a cool overhaul with blue suede boots and a letterman-style jacket

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Yara Shahidi gives her black chiffon dress a cool overhaul with blue suede boots and a houndstooth, letterman-style jacket.

Celebrities Wearing Boots and Dresses: Florence Pugh wears a printed dress with velvet boots

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We can't blame Florence Pugh for donning Chloé top-to-toe, particularly when it involves a gorgeous floral maxi dress and rust velvet booties.

Celebrities Wearing Boots and Dresses: Meghan Markle in black boots and a dress

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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.

Celebrities Wearing Boots and Dresses: Gigi Hadid in a green dress with boots

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There's something about this look that feels very un-Gigi Hadid, but we're here for it.

Celebrities Wearing Boots and Dresses: Rosie gives her slinky velvet dress a cool spin with the addition of black leather ankle boots.

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

Celebrities Wearing Boots and Dresses: We can always rely on Kate Bosworth to give her ensembles a unique twist, as this floral H&M dress and studded biker boot combination proves.

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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.

Celebrities Wearing Boots and Dresses: Alexa Chung wore a floral shirt dress and cowboy boots, so we wore a floral shirt dress and cowboy boots.

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

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

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

Celebrities Wearing Boots and Dresses: Poppy Jamie looks incredibly chic in this pink jacquard midi and black sock boot ensemble, which she wore to an Alexa Chung-hosted party last Christmas.

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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.

Celebrities Wearing Boots and Dresses: Thanks to Victoria, we'll all be coordinating our bots with an accent roll-neck worn underneath a printed dress this autumn.

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Thanks to Victoria, we'll all be coordinating our boots with an accent roll-neck worn underneath a printed dress.

Celebrities Wearing Boots and Dresses: 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.

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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.

Celebrities Wearing Boots and Dresses: Emily Ratajkowski ups the ante of her simple back dress with a pair of bright snake print boots. Inspired.

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

Celebrities Wearing Boots and Dresses: Rochelle Humes has won us over with her style this season, with this Topshop daisy-print dress and patent boot look serving as one of our favourite looks.

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

Celebrities Wearing Boots and Dresses: Busy Phillips' flash of pale leather boots underneath her Doên was a pleasant surprise.

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

Celebrities Wearing Boots and Dresses: All hail Katie Holmes' recent style metamorphosis, which has included this incredibly yellow floral maxi and lace boot outfit.

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

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

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

Celebrities Wearing Boots and Dresses: 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.

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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.

Celebrities Wearing Boots and Dresses: Blue suede boots and a graphic brown and camel dress. We dare ask, does Sienna ever get it wrong?

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

Celebrities Wearing Boots and Dresses: Model Sam Rollinson expertly clashes her floral midi dress with a pair of on-trend snake print ankle-grazers.

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

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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.

Celebrities Wearing Boots and Dresses: Only Rihanna could leave us wanting to wear a split-hem, leopard dress with red over-the-knee boots.

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

Celebrities Wearing Boots and Dresses: It seems that even Priyanka Chopra wasn't able to resist the allure of cowboy boots this season.

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

Celebrities Wearing Boots and Dresses: Queen of the dress-and-boot combination is undoubtedly Anna Wintour, who has worn the failsafe duo for decades.

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

Celebrities Wearing Boots and Dresses: Metallic boots and polkadots make for a fresh outfit pairing, as evidenced by Pixie Lott.

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

Celebrities Wearing Boots and Dresses: Leomie Anderson's lumberjack checks were made to be worn with hiking boots.

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

Celebrities Wearing Boots and Dresses: This berry striped knitted dress and purple slouch boot duo is as close to perfection as you can get. Bravo, Zendaya.

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

Celebrities Wearing Boots and Dresses: Checked boots are hard to come by but, when you do, you'll want to wear them with a bright, block colour dress like Adwoa Aboah.

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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.

Celebrities Wearing Boots and Dresses: Been the colour of your dress to your boots like Margot Robbie for a fast-track to chic.

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

Celebrities Wearing Boots and Dresses: 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.

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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 late-winter style, too.