Jo Rosenthal
Writer
The Mansion Diner1634 York Ave, New York
Jo wears a cropped Oxford shirt designed by JW ANDERSON along with a draped sweater and wide chinos. Pictured in an iconic preppy outfit outside the Mansion Diner, an Upper East Side institution that’s been open for eight decades.
The pajama set works great with the breezy ultra light jacket from UNIQLO : C. Remixing classic items is how new styles are born.
Flynn McGarry
Chef
At twenty-six, Flynn already runs two dining establishments in New York. Classic preppy details like the casually draped sweater, rep tie, and cuffed chinos advertise his confident demeanor.
Wearing a polo shirt that looks straight off the tennis court with a saxe blue Oxford shirt tied around the waist, Flynn visited Rita & Maria, a Brooklyn cafe run by his friend Sarah, who appears below.
Rita & Maria558 Halsey St, Brooklyn
Adinah Dancyger
Filmmaker
Boasting a string of sunny booths, the Square Diner in Tribeca has been in business for over a hundred years. Adinah, a filmmaker who grew up in Manhattan, came here often as a kid. The tidy look of the ribbed polo cardigan and slacks is balanced by the bright yellow and the nuanced fading of the denim shirt, giving the outfit pop. One of the main rules of preppy style is to always bend the rules.
Square Diner33 Leonard St, New York
Brian Oakes
Artist
Skillfully incorporating British items is another standard tenet of the preppy style. An artist who once worked in the studio of Tom Sachs, Brian wears a single breasted coat with British flair. BLOCKTECH ensures the coat will stand up to the rain, but it’s much lighter than your average slicker. To balance off his trim look, Brian wears boat shoes without socks, adding a rich note of color that matches his burgundy sweater.
Jerico Island
Musician
Rap artist and model Jerico Island pairs a tried-and-true navy blazer with chino shorts and a bright bag for a relaxed preppy mood.
On the right the green polo shirt he wears outside Mike’s Coffee Shop, a beloved Brooklyn diner, is perfect for this tranquil morning scene. His wide chinos are nonchalantly rolled up to the ankles.
Mike's Coffee Shop328 Dekalb Ave, Brooklyn
Danielle Opatovsky
Landscape Designer
Taking in the sun from a bench in Central Park, Danielle is the owner and designer of Etta, a garden design studio. Her outfits center on simple items stylishly dressed down. Highlights include the loosely knotted regimental stripe tie (left) and the pop colors on the rugby shirt tied around her waist (right). Another strength is how she combines basic colors like blue and gray, or green and off-white.
Dylan Pearce
Photographer
Dylan steps out of the Square Diner in a pink gingham shirt, a new item this season. The heavy duty canvas blouson goes great with the chino shorts, a perfect springtime combo.
Reading at the table, he wears his jeans without a belt and his shoes with no socks, unbuttoning his collar and rolling up his sleeves. A rugby shirt tied over his shoulders adds an interesting touch to this rugged Ivy outfit.
The Mansion Diner1634 York Ave, New York
Sarah Abramjuk
Owner of Rita & Maria
Sarah runs Rita & Maria, a cafe and bar in the Brooklyn neighborhood of Bed-Stuy, where fashionable residents convene for the day’s assortment of pastries. She wears the new Black Watch shirt tucked in, leaving the collar and most of the placket unbuttoned. Her style demonstrates how an individual approach can influence the look of even the simplest items.
Rita & Maria558 Halsey St, Brooklyn