Ankle Boots With Dresses Are Out—This Is the Shoe Trend Those With Cool Style Are Wearing Instead

I suppose that since so many aspects of fashion are subjective and what we wear is dependent on one's taste and lifestyle, you can take what I'm saying with a grain of salt and just wear whatever you want. But if you're curious about what I'm seeing stylish people wear (and not wear) as of late, I'm here to provide that information. The specific stylish person I'm putting on your radar this time is Alexa Chung.
Chung has provided us all with countless examples of outfit and trend inspiration over the years, and the latest is one for the books. This week in Manhattan, she was photographed, ironically, at a photo shoot. And one of the looks she wore was perfectly executed and very much in keeping with her signature style. The simple outfit consisted of a white maxi dress and the boot trend that looks much fresher than ankle boots would have with a maxi dress: knee-high boots (specifically, black patent-leather ones).
Don't get me wrong—ankle boots are a classic that serve an important purpose in one's wardrobe. But I'm not seeing fashion people pairing them with any dresses, let alone maxi dresses, all that much lately. It's almost always knee-high boots they opt for, and I predict that as fall inches closer and closer, we'll see other stylish dressers follow Chung's lead and pair maxi dresses with knee-high boots.
Keep scrolling for fresh Alexa Chung styling inspiration and to shop similar maxi dresses and knee-high boots to get the look.
Shop White Maxi Dresses
Shop Black Knee-High Boots

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
If You've Already Ordered This Pretty Winter Trend Celebs Just Started Wearing, You Have Good Taste
Spotted on It girls in Paris and NYC.
-
Everyone Stylish in Paris Is Suddenly Wearing This 2025 Color Pairing to Avoid "Boring" Outfits
Spotted at the Miu Miu show.
-
The Fall Shoe Trend Everyone in Paris Is Wearing With Black Leggings to Runway Shows and Dinners at Chez Janou
Hint: It's not sneakers or ballet flats.
-
Nothing Humbles Your Closet More Than the Zara New Arrivals Section—25 Pieces to Instantly Elevate Your Fall Outfits
Did I mention they're modeled by Alexa Chung?
-
It's Official: Everyone With Good Style Will Wear These 2 Colors Together in 2026
As seen on Alexa Chung in Paris.
-
I Live in NYC—These Are the 8 Anti-Trend Fall Pieces That Always Get Me Compliments
From everyday loafers to preppy polo sweaters.
-
*Not* Ankle Boots—the Rich-Looking Shoe Trend That's Quietly Taking Over for Fall 2025
Shop the style inside.
-
Cozy Cashmere! Sleek Suede! Dark Denim! 32 Affordable Fall Pieces You'd Find in a Wealthy Person's Closet
Oh, did I mention they're under $250?