How the Chicest Celebs Are Wearing Dresses and Boots Right Now
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.
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.
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.
Yellow suede boots may sound daunting to wear, but Cynthia pulls them off like it's no big deal with a printed Zimmerman dress.
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.
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.
Yara Shahidi gives her black chiffon dress a cool overhaul with blue suede boots and a houndstooth, letterman-style jacket.
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.
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.
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 boots with an accent roll-neck worn underneath a printed dress.
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.
Blend 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 late-winter style, too.
This post was originally published at an earlier time and has since been updated.
Next: Our Editors Think These 4 Boots Go With Every Dress They Own
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.
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