The Preppiest Thing I Own

There’s more to the preppy aesthetic than pink shirts and repp ties (though we do love both—especially when worn together). Ultimately prep is about what happens when you combine a reverence for tradition and quality with an irreverence for the rules. With that in mind, we asked six stylish friends to tell us the one thing that most embodies that attitude for them.

A working fireplace takes center stage inside David Coggins’ carefully curated, large-scale cabinet of curiosities (which also happens to double as a West Village apartment). The space is stacked with an abundance of books, vintage textiles, posters, found photographs, and trinkets that adorn the few tables he’s placed throughout his living space. The regular RL Mag contributor is also a New York Times best-selling author of the book Men and Style. The way he gets dressed is most certainly preppy, but not fussy. He’s a walking lesson in style. And his item of choice—a book given to him by his father—holds its own lessons.

“I went to college in Maine, and when I graduated, my parents gave me this first edition of The Great Gatsby. I’m from Minnesota, and I went to the same high school that F. Scott Fitzgerald went to, St. Paul Academy. I was incredibly touched. As I opened it, my father said to me, ‘Turn to the first page, and read the first line,’ so I did. The first line is: ‘In my younger and more vulnerable years my father gave me some advice that I’ve been turning over in my mind ever since. Whenever you feel like criticizing anyone, he told me, just remember that all the people in this world haven’t had the same advantages that you’ve had.’ I appreciate the present since it was an amazing thing in its own right. But also represented a connection with my family and my own history.”

Fred Castleberry’s Brooklyn, New York, apartment reflects the way he gets dressed—it’s a riot of curated maximalism. Every surface presents findings from his travels—a pair of intricate slippers perfectly situated atop a tartan scarf, a wall of found and taken photographs held together by schoolyard link chain, and stacks of books with an eclectically unified point of view on style, food, and travel.

All of which is to say that the designer and photographer—he goes by F.E. Castleberry professionally—has a well-formed POV on prep. As we found out, it even carries through to flatware. He eats every meal—breakfast, lunch, and dinner—with a vintage ’50s sterling silverware set.

“I was visiting this vintage place in Rhode Island with my friend Kyle, and I came across this set and thought, ‘Why not just eat with sterling silver every day?’ With the idea of preppy style there is always a functionality before form. To me, it’s not just acquiring things because they’re beautiful. Inherently they have, and should have, some sort of function. There’s this quote by William Morris that I really love: ‘Have nothing in your house that you do not know to be useful, or believe to be beautiful.’ Every time I eat, I take out the set, and it makes me smile. It’s a nice little luxury.”

Like virtually everyone in media in 2019, “I wear many hats,” says Matt Hranek over morning coffee at his Park Slope home. “I started out as a photographer, ended up as an accidental TV host, then made my way to magazines and creative direction. And now, I’m the founder of a men’s lifestyle magazine”—Wm Brown—which pays homage to the people, places, and things that inspire him (and the 40-odd thousand people who follow him on IG). His pick, a Leica M2 rangefinder, represents an unexpected side of prep.

When you ask Alex Assouline to describe his job as a VP at Assouline Publishing, the luxury book company founded in 1994 by his parents, he’s very matter of fact. “When the book is done, that’s when I get involved. I drive sales, distribution, and marketing for our titles and other projects.” The 26-year-old New York resident (by way of Paris) is also spearheading the house’s new interior design initiative, crafting libraries for private residences, hotels, and commercial projects, bringing titles to the spaces that speak to the people who inhabit them as well as found objects and accessories. Here, he tells us why suspenders, his sartorial moniker, always come first.

“I’m not much of a shopper. In fact, I shop for two suits a year. It’s what I feel good in—a nice way to present myself for potential clients, partners, and people that I work with. It’s just what I’m comfortable in. And every day, I wear suspenders. I’ve been wearing them daily since I was 15. One day, I was going through my father’s closet and I found his collection. I was intrigued because I didn’t see people wearing suspenders, especially in modern movies. That’s where my infatuation began, and it really took off from there. I would search online and at flea markets for ones to help build my collection. I always gravitate toward suspenders that aren’t plain. I like there to be a bit of a motif or color, and I’m always trying to build my collection. Above all, there’s a practicality to suspenders: They hold your pants up. While some people have their finishing touches and routines they do before they walk out the door, this is my first touch, so to speak. I choose a pair of suspenders first thing in the morning, and I work my outfit around that.”