Turn It Up: Jai Lennard's Preppy Style Has A Smooth, Jazz Soundtrack

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Jai Lennard, Photographer
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If it looks like Jai Lennard has been shopping in your grandfather's closet, well, you're wrong. He's probably been shopping in his. The photographer has got a knack for preppy ensembles that have a bit of old-school flair. Not to mention, a style soundtrack so smooth that we're sure Miles Davis would approve. But don't be surprised if this risk-taking artist throws you a few curves balls aside from his self-proclaimed "eclectic" taste. His provocative and sometimes erotic artwork is a must-see — and a NSFW must-see at that. Trust, from his getup to his photography, Lennard is a style star who knows how to get us talking.
My style in six words or less:
"Casual prep without all the flair."
My constant source of style inspiration:
"My grandfather. He has two walk-in closets."
The dressing difficulties I've had to overcome:
"I'm eclectic in my style and usually dress for the occasion. This leaves me often trying to figure out what kind of occasion I'm about to go to."
My first major, big-ticket style purchase:
"Leather-jacket hoodie when I moved to New York."
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My favorite up-and-coming designers:
"All my friends have different styles, so that's hard to say. Though, Tim Coppens is one of the only fresh designers I could currently see myself wearing."
My most surprising, out-of-left-field fashion find:
"Only one person in my life has dared to buy me shoes, and I didn't know them that long when they did. The shoes are the brown loafers by Pierre Cardin, and I wear them to death."
My style theme song:
"Cannonball Adderley, 'One for Daddy-O.'"
My definitive summer go-to outfit:
"My Ralph Lauren shorts, a good loafer, loose T-shirt, and Woolrich hat."
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Styled by Laura Pritchard, Hair by Bethany Brill, Makeup by Tiffany Patton
Look 1: Ralph Lauren white button-up shirt; Gap herringbone trousers; Banana Republic black belt; Vintage tan sandals; Rolex watch; Surface to Air rings; Butch black frame glasses; Alexander Olch Wrinkled Plaid Bow Tie, $29, available at Barneys New York.
Look 2: Vintage green jacket; Ralph Lauren blue button-down; Ralph Lauren skull khaki shorts; Pierre Cardin vintage brown sandal; Woolrich brown hat; Butch black frame glasses; Rolex watch; Surface to Air rings.

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