Well-Dressed Celebs Have Basically Stopped Wearing These 3 Shoe Styles With Leggings

As I was scrolling through pictures of celebrities wearing leggings, I was reminded that celebrities never stopped wearing them, even though the internet routinely claims they're "back." What fluctuates is the way in which people wear leggings. Currently, celebs are wearing them as pants more often rather than as athleticwear for Pilates class and the gym. They've also been more creative with how they style them for workouts lately. It's a fun development, and it makes the rest of us want to get creative with leggings too. One of the ways to do that is via the shoes we wear with them, and celebs have been providing plenty of inspiration in that arena.
Below, I've highlighted five specific shoe styles celebrities are reaching for when they wear leggings and three they never do, just in case you're wondering. Scroll on to see Hailey Bieber, Gigi Hadid, and more celebrity legging wearers, and shop the shoe styles they're prioritizing.
The Skips: Ankle Boots, Stilettos, Platforms
I'm well-versed on celebrity legging outfits given my job, and I couldn't tell you the last time I saw a celeb wearing leggings with ankle boots, stiletto heels, or dressy platforms. I'm not surprised in the least, as these three styles tend to make leggings look dated and don't balance out the tighter-than-tight pants proportionately the way that, say, sneakers or knee-high boots do.
Chunky Knee-High Boots
Chunky knee-high boots with leggings are a cool, flattering combination that celebrities love to wear in the fall and winter. Knee boots are the go-to way to dress leggings up. See Bella Hadid below for proof. (Kendall Jenner is another celeb fan of the pairing.)
On Bella Hadid: ALO High-Waist Airlift Leggings ($125); Saint Laurent coat and Y Tote Shoulder Bag ($3600); Miu Miu Leather Boots ($2550)
Shop Chunky Knee-High Boots
Slipper Shoes
If you love the ease of flip-flops with leggings but not the look, consider a pair of slipper shoes—a major trend for spring. They're effortless and chic, as Laura Harrier recently proved.
On Laura Harrier: Saint Laurent Le 5 à 7 Supple Leather Shoulder Bag ($2650)
Shop Slipper Shoes
Chunky Sneakers
Chunky sneakers, especially with crew socks, give leggings that '90s feel that celebs like Kaia Gerber love. It's also the most comfortable shoe style on this list, so there's that.
On Kaia Gerber: Adidas hat; Asics sneakers
Shop Chunky Sneakers
Ballet Flats
If you like your legging outfits to look prettier than average, do as Bieber did earlier this year and wear them with ballet flats. Her elastic-strap pair gave her outfit even more of a ballerina feel.
On Hailey Bieber: Saint Laurent bag; The Row Leather Ballet Flats ($820)
Shop Ballet Flats
Sporty Sandals
Sporty sandals such as flip-flops, Tevas, and Birkenstocks are a natural pairing with leggings. Gigi Hadid, Harrier, Gerber, and Jenner are also fans—often with the addition of crew socks.
On Gigi Hadid: Lack of Color hat; Arizona Love Trekky Flower Mix Sandals ($173)
Shop Sporty Sandals
Shop My Legging Picks

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.
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