I don't usually like to definitively say to wear one thing with another. After all, style is personal, and if you want to get creative with your pairings, I'll be your biggest cheerleader. That being said, certain fashion duos just work, and Dakota Johnson and Laura Harrier have one down to a science.
The combination in question is baggy jeans worn with kitten heels, a matchup that perfectly combines the relaxed, casual look of denim with the shoe style's air of easy elegance. A slight heel also keeps a slouchier denim silhouette from puddling and catching on the floor, making the twosome practical as well as aesthetically pleasing. This is a fact that Johnson and Harrier both appear to understand clearly.
Harrier debuted the tried-and-true ensemble first while in Milan for the spring/summer 2025 men's shows. The White Men Can't Jump star was spotted in the Italian fashion capital popping into a convenience store wearing a loose and billowy Toteme shirt straight out of Call Me by Your Name (very location-appropriate, I'd say) with baggy denim, a vintage Fendi bag, and a pair of slightly heeled black mules with an almond-toe shape. To finish off the outfit, she added a Tiffany Co. cuff, silver hoops, and her go-to oval-shaped sunglasses.
On Laura Harrier: Toteme Relaxed Fit Plaid Linen Blend Button-Up Shirt ($680); Elsa Peretti Split Cuff ($1800)
Soon after, Johnson left Jimmy Kimmel Live! in Los Angeles wearing another variation of the same combo, mostly by Sabato De Sarno's Gucci. For the talk-show appearance, she embodied glamour in a modern age, donning a loose updo with cat-eye sunglasses and big gold hoops in a loosely buttoned cardigan, relaxed split-hem jeans secured with a tiny brown-and-gold Gucci belt, and off-white patent-leather slingback kitten heels. A dark-green Gucci Jackie 1961 bag can be seen tucked under her arm.
Though different and unique to the two actresses' personal style preferences, both outfits prove that, when it comes to what shoes you should wear with baggy denim, one option is far and wide superior. Scroll down to see Johnson's take.
On Dakota Johnson: Bottega Veneta Bold Ribbon Narrow Sunglasses ($485); Gucci Signoria Slingback Pump ($1150)
Shop the best shoes to wear with baggy jeans:
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Not Classic Ballet Flats, Not Loafers—Everyone With Cool Style Will Be Wearing These Shoes With Black Trousers in Fall 2025As seen on Katie Holmes.
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I Just Started Investing—31 Chic Pieces That Will Have Me Dressing the PartEffortless and elevated is the goal.
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Summer or Fall, This Is the Casual But Elegant Flat-Shoe Trend That Always Looks Good With JeansAs seen on Jennifer Aniston.
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Spotted on Zoë Kravitz on a Stroll With Harry Styles: Fall 2025's It-Girl Denim TrendTheir style is already in sync.
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There's No Question—These 8 Fall Shoe Trends Will Make You Look RichLuxe outfits are in your future.
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Better Than Ballet Flats (and Loafers): The Shoe Trend It Girls in NYC and Paris Will Be Wearing This FallThey're classic but fresh at the same time.
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The Numbers Don't Lie: This Is the Only Denim Trend More Popular Than Baggy Jeans Right NowAccording to data.
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I'm an NYC Shopping Editor—I Can't Stop Thinking About These 31 Rich-Looking Fall Finds FromReplica Store, Zara, and H&MDid I mention they're under $250?
