Selling Suits to Sinatra

An extended interview with Richard E. Press

A little after 8 a.m. on a warm morning in late summer, I was setting up for an interview in the beautifully appointed J. Press store across from Grand Central. I had been to the J. Press Flagship Store in New Haven a couple weeks earlier, but I needed one missing piece to finish my filming of J. Press—an interview with the legendary Richard Press. As you know, his grandfather founded J. Press, a menswear institution of the last century. While I had met Richard in passing, I hadn't had the pleasure of having an extended conversation with him, and I was looking forward to this opportunity very much.

He walked in, and after getting a spritz of cologne from the St Johns sampler on the counter—his ritual upon entering the store, he said—I shook his hand and began giving him an overview of what I was looking to accomplish with the interview, the standard message I give everyone I interview. He quickly stopped me and said he does better without knowing too much about the interview—just turn on the cameras, and let's start, he said. So I did! And what ensued was terrific.

Richard, in his signature bow tie

Our conversation, which lasted 45 minutes, was not only thoroughly enjoyable and entertaining but also highly educational. In my main video about J. Press, we only used a few minutes of the half-hour of amazing stories Richard shared. However, I was left with so many more fascinating stories and anecdotes that didn't necessarily fit into the narrative of the brand profile. Yet, I was eager to share them because I knew people would love to hear them. This led me to the idea of starting a new concept for additional videos. I wanted to publish these long-form interviews as an addendum to the brand-focused videos, providing a deeper understanding of the brands I feature, in this case J. Press. Expect more of these moving forward, and I’m thrilled to start these interviews with Richard.

I had read Richard's books and liked his writing, but seeing him bring these stories to life on camera took these incredible stories to a new level. It turns out that Richard was a theatre major and spent some time acting in his early years, which comes across in the interview as he knows how to tell a story. I remember thinking that once the interview concluded, I was proud that he trusted me to share his and his family's business story. I know he's not done many video interviews, so I felt a sense of responsibility, as true fans of J. Press would love hearing from Richard directly. They might have met him at a store event over the years, but getting him for thirty-five minutes to allow loyal brand fans to learn more of the behind-the-scenes story will only grow their passion for the brand, and I'm thrilled to publish the full interview today.

Richard (center) in his college days

During the conversation, I delved into many aspects of Richard's life, from his cherished memories of his grandfather to his experiences selling suits to a-list celebrities such as Frank Sinatra and Cary Grant. His unique perspective and personal anecdotes make this interview a must-watch for any menswear enthusiast. I couldn't resist asking about his encounters with the legendary Frank Sinatra, and Richard did not disappoint with his incredible stories. He shared about selling suits to the iconic singer, but also regaled us with a particularly entertaining (and late) night out that involved a few Jack Daniels and the Rainbow Room.

We also discuss his unique perspective on the Ivy Style movement and his role in shaping the J. Press brand. I won't spoil it too much, but you'll love this whole interview if you are a fan of the brand. If you're unfamiliar with J. Press, I think you'll become a massive fan after listening to this conversation.

Regardless of your entry point, I'm thrilled to bring you this video. Richard is a menswear legend, and I'm honored to be able to bring you this interview. I hope you'll give it a watch!