
Katie Holmes gave the cowboy boot trend a downtown spin while filming “Happy Hour” with Joshua Jackson in New York City on Monday. Her boots, a vintage-looking pair with square toes and a worn caramel finish, brought a touch of Western edge to an otherwise low-key look.
Katie Holmes and Joshua Jackson are seen on the set of “Happy Hour” on July 21, 2025 in New York City.
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The leather was visibly creased across the vamp, hinting at real wear, while the stacked angled heel and clean shaft lent structure. With no visible hardware or embroidery, the silhouette read minimal but unmistakably cowboy-coded.
A closer look at Katie Holmes’ boots worn on the set of “Happy Hour” on Monday.
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The footwear choice builds on Holmes’ recent history with earthy leather. At the Printemps NYC opening in March, she paired sculptural-heel brown sandals from Tory Burch’s fall runway with a deer-spotted midi dress from the same collection. Those sandals had polish, while these boots feel lived-in. Both are deliberate and tonal.
It’s a notable departure from her usual off-duty picks. While Holmes is known for her collection of ballet flats, Adidas Sambas and city-leaning sneakers, these boots offer more grit. For an actress who rarely overdresses in public, it’s a subtle shift with style implications — suggesting either a character wardrobe cue or a personal pivot toward grounded, transitional dressing.
Katie Holmes
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Holmes styled the boots beneath loose, floor-grazing navy trousers that created a long, uninterrupted line down the leg. The slouchy fit offset the boots’ sturdiness, keeping the outfit casual rather than costume. She layered a heather gray tank under an oversize pink plaid shirt, worn open and unbuttoned, completing the look with her signature ease.
She’s not alone in getting a head start on fall. Tina Knowles recently wore black leather boots with a curved collar to the Bluemarble show in Paris, while Selena Gomez has favored midcalf biker styles from Paul Andrew while filming “Only Murders in the Building.” The return of the boot — square toe, block heel, unshiny — is starting to take shape, and Holmes’ version fits right in.
With “Happy Hour” marking a much-anticipated onscreen reunion between Holmes and former “Dawson’s Creek” costar Jackson, it’s fitting that her wardrobe hints at something familiar yet evolved.
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