Hold the Sneakers—This Is the Fall Flat-Shoe Trend to Wear With Shorts Starting Now
Shop the casual way Harry Styles wears it.
Yes, we still have a few more weeks left of summer, but it’s about time to retire those sneakers (and sandals) you’ve been wearing all season. There’s another shoe trend you must try out for your pre-fall looks, and no, it’s not ballet flats like the pair he wore at this year's Grammy Awards; it’s something even chicer, and maybe a little unexpected. The shoe trend is boat shoes. And before you think of a rebuttal about them being played out, just know that Harry Styles was just spotted wearing a pair.
In between shows at Madison Square Garden, Styles was seen taking a stroll in a casual off-duty outfit. With his boat shoes, he wore a graphic tee, oversized green shorts, and a brown woven straw shoulder bag. While boat shoes aren’t a particularly new trend, Styles made them look fun and fresh with his chosen outfit. The shoes made him look put-together in a way that sneakers may not have. Boat shoes are absolutely having yet another resurgence, with Prada, Saint Laurent, and Miu Miu releasing new iterations for fall, and I won’t be surprised when they’re everywhere by October.
If you agree and want to dress up your casual shorts outfits before it’s time to start layering, keep scrolling to recreate Style’s outfit and shop for more chic boat shoes.
How Harry Styles Wears It
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Kerane Marcellus is a New York-based writer. She joined the Who What Wear team in 2025 after writing for Essence Magazine and freelancing for a number of other arts and culture publications. Fashion is a form of expression that she encourages everyone to take part in. There is no right or wrong in getting dressed! When she's not writing, she's reading in the park or gallery hopping in the city.