Harry Styles’s Shirt Plays It Loose on Date Night With Olivia Wilde

If you’re dating a man like Harry Styles, you’ll have to let him steal the fashion spotlight at times. Ahead of a monthlong string of concerts at New York City’s Madison Square Garden, Styles was spotted out and about last night with his girlfriend of over a year-and-a-half, Olivia Wilde. The pair was snapped exiting the restaurant Rubirosa, a dimly lit SoHo spot known for its cozy Italian-American fare.

Wilde looked effortlessly elegant as she mastered a classic NYC day-to-night look. She paired a well-cut navy t-shirt with a blue toilé high-waisted maxi skirt punctuated by buttons running down the front. She emphasized the casual vibe with a pair of Adidas tennies and a canvas tote from The Vampire’s Wife.

Ever the maximalist, Styles continued his well-documented love affair with crochet tops. This one was a long sleeve button-up with a very loose knit. As if to maximize the amount of skin showing, he left it unbuttoned to below his sternum. He finished the look off with a pair of wide-leg pants and simple white sneakers.

August is notoriously one of New York City’s most humid and casual months (half the town’s power players are out of office, traveling the globe on summer vacation before reality sets back in post-Labor Day). So Styles and Wilde’s choice to lean into more laid-back looks while still retaining their own style is a smart style answer to the question, “How should I dress in Manhattan in August?”

Expect to see a lot more of the pair in the Big Apple over the next few weeks. Styles’s Love on Tour already hit NYC for multiple dates back in October 2021, but he’s settling into the city with an impressive 15-date residency that will run into late September. At some point during the run, expect the pair to likely take a quick jaunt over to Italy: their film, Don’t Worry Darling, which Wilde directed and in which Styles co-stars alongside Florence Pugh, will premiere at the Venice International Film Festival in early September.

Of course, that means we’re in for an entire month of Harry Styles’s on-stage fashion, Harry Styles’s NYC street style, and Harry Styles’s leading-man red carpet style. His stylist is sure to be busy.