Harry Styles and Zoë Kravitz took two very different trending shoes off duty in New York on Wednesday. The two are style icons in their own right. Bring them together, and they become a fashion power couple.

In addition to luxury red carpet moments, the pop star and the actress/filmmaker have both perfected the effortless off-duty urban look, and that was particularly evident in their footwear choices on Wednesday when they were photographed separately in New York City ahead of night one of Styles’ Madison Square Garden residency.

NEW YORK, NY - AUGUST 26: Harry Styles departs his apartment on the way to the first night of his residency at Madison Square Garden on August 26, 2026 in New York City.  (Photo by XNY/Star Max/GC Images) *** Local Caption ***Harry Styles

Harry Styles

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Styles embraced the boat shoe resurgence for the second day in a row with Prada’s Shuffle antiqued leather lace shoes, a slim, dark brown leather style with an almond toe, minimalist leather lacing and a vintage finish.

He paired the shoes with white crew socks and a New York Philharmonic shirt from the ’90s which he French tucked into sporty green shorts. Looking like he could be heading to the beach rather than a stadium (save for his shoes), he also toted a large brown woven bag.

NEW YORK, NY - AUGUST 25: Harry Styles is seen on August 25, 2026 in New York City.  (Photo by XNY/Star Max/GC Images) *** Local Caption ***Harry Styles

Harry Styles

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The day prior, the English artist showcased an entirely different way of styling the same Prada shoes. He went with a breezy formal look, a sort of a Mr. Darcy-takes-NYC aesthetic with a billowing white button-down partially tucked into loose brown trousers.

NEW YORK, NY - AUGUST 26: Zoe Kravitz is seen on August 26, 2026 in New York City.  (Photo by XNY/Star Max/GC Images) *** Local Caption ***Zoe Kravitz

Zoë Kravitz

XNY/Star Max/GC Images

Meanwhile, while Styles was having a boat shoe moment, Kravitz embraced another trending footwear style: the kitten heel.

Her minimalist black sandal added a touch of elevation and formality to her shorts-and-T combo. She frequently wears styles from The Row, so it would be no surprise if she was wearing the luxury brand’s Combo Two Slide, featuring a structured front strap and a tapered heel measuring 1.6 inches.

Their shoe styles were different, but Styles and Kravitz found some fashion synergy on Wednesday with their choice of T-shirts. While the “Kiss All the Time. Disco, Occasionally” artist wore a vintage New York Philharmonic shirt, Kravitz wore a T reading Barneys New York — another throwback shirt referencing the city in which Styles will complete his 30-night residency. Kravitz wore her white top with black mini shorts and a white headband.

A closer look at Harry Styles' boat shoes and Zoë Kravitz's kitten heels.

A closer look at Harry Styles’ boat shoes and Zoë Kravitz’s kitten heels.

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Discover more of Kravitz’s eclectic shoe style below.