“This has already been such a journey with Josh—he’s so fun and sweet, and we just laugh all the time,” he adds. “We decided to really play with his fashion. This is still a very new relationship for both of us; I’m happy it’s resonating with people.” Bolden likes to start each new styling relationship with a long conversation. O’Connor shared an image of an artist’s work he loved with Bolden, and they used that as an ongoing reference. “Josh is a true artist, and it allows you to be an artist too,” Bolden says.
Their first sartorial coup came at the start of the press tour in Paris, in the form of a cropped, patterned Lemaire V-neck knit paired with a brown-and-blue-dotted zigzag-pattern shirt over black jeans. With the mix of patterns, textures, and old-school shapes, the look felt both playful and classic, as well as a little nostalgic. “We all had something like that knit as a kid, and on Josh it just looks so cool,” says Bolden. Then they added an elegant slim gold Cartier Tank Américaine watch on top of his Lemaire-shirted wrist—O’Connor wanted the impressive timepiece to be on show, and Bolden styled it out. It’s just one of many moments when their penchant for subtle personality dressing has come into play.
Moving from press engagements in London to the U.S., there was a hazy brown three-piece Loro Piana suit, some relaxed dress pants, a swirling purple paisley tie via Dries Van Noten, and a softly structured suit by The Row atop an airy striped blue shirt. For his appearance on The Tonight Show, O’Connor wore a butter yellow Dior shirt with a collar that stood to attention. Two very different Simone Rocha suits—one white and workwear-y, the other black pinstripe with a floral brooch—offered some whimsy too. Experimenting with suiting silhouettes and accessories—like a wing-collar shirt, a watch over a cuff, or a pair of Jacques Marie Mage sunglasses—adds to the storytelling.
“We’re playing with proportions,” explains Bolden. “We’re doing something that might seem classical, modern, and simple, but that’s one of the hardest things to execute. His style is easy, lived-in, effortless.”
And of course, for a house ambassador, there’s a lot of custom (not to mention fresh-from-the-runway) Dior. For the Paris premiere, O’Connor wore a custom tailcoat jacket with thick cable-knit braids; kept monochromatic and paired with silky suit pants, black shirt, and tie, it felt super playful yet sleek—and all very him. “This is classic Josh: cozy, easy, fun,” adds Bolden.
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