Don’t Wear a Wrap Dress and Other Valuable Lessons Learned From Chief Judge Judith Kaye
4.7.2026
On Jan. 7, we marked 10 years since the passing of Judith S. Kaye, the first woman to serve on the New York Court of Appeals and to this day its longest-serving chief judge. During her lifetime, Judge Kaye was recognized and lauded for her brilliant legal mind and innovative executive skills and in death she was rightfully and permanently enshrined as a bright star in the legal firmament. I will always be in awe of the mark Judge Kaye left on New York jurisprudence, and I know I am not alone.
When I think of her now, however, as I have almost every day for the past decade, it’s not because of her legal acumen; rather, more often than not it is the smaller moments and helpful lessons I learned from working closely with her and observing her interactions and habits during what she dubbed her post-Court of Appeals “afterlife” or sometimes her “second act” at the law firm of Skadden, Arps, Slate, Meagher & Flom that come to mind.
To have known Judge Kaye as a jurist and as a formidable lawyer was to only know a small part of the whole of who she was. An incomplete description of her attributes might also include devoted wife, mother, grandmother, friend, serious reader, incomparable grammarian and ruthless editor of her own written word, runner and walker, patron of the opera, lover of the theater and of New York City and New York State in equal measure. All these aspects of Judge Kaye the person were not necessarily apparent to the general public, but her status as a legal luminary belies her impact on those who knew her personally and benefited from observing how she moved through the world and conducted herself. I am one such beneficiary.
At the time I began to work with Judge Kaye I was not sure whether I could continue to practice law. My husband also worked in a big firm and we had three young kids, the youngest just a year. I was feeling intense pressure to leave the legal profession altogether – a feeling undoubtedly familiar to many lawyers with families. But when the opportunity to work with Judge Kaye arose, I could not turn it down. I expected challenging and interesting work at a high level, and she delivered. What I did not expect was that as a mother of three grown children herself, she understood the phase of life I was in and what it meant to have a young family. Sheryl Sandberg’s book “Lean In” was a topic of much discussion back then, but Judge Kaye, ahead of her time as usual, was skeptical. She mused that in her own career she did not “lean in” as much as “hang in.”
Perhaps because she felt she owed her career to “hanging in” she downplayed the active role she played in her own successes and preferred to demur when asked for advice. “I don’t give advice,” she would say, “except, don’t wear a wrap dress.” For those not in the know, the idea of a “wrap” dress is to enable the wearer to get dressed quickly and look pulled together by wrapping one garment around the body. However, a wrap dress means any strong wind or careless dive into the back of a taxi carries the potential for exposure of one’s non-legal briefs. She was joking but also communicating effectively one of her bedrock principles: there are no shortcuts or substitutes for preparation and care in how you present yourself professionally and personally. She also understood that a wrap dress, like the notion of work-life balance, is a great idea in theory but ultimately a mirage.
Clothing was important to the judge, and she was always impeccably dressed. I can see her now in a well-loved designer suit and Forever 21 scarf in blue and orange – New York City’s colors – and she was well-known for wearing red shoes under her judicial robes. She understood the profound power clothes can have to communicate. While she was on the court, she spoke about wanting more red shoes on the bench – her winking way of advocating for more women judges. In recognition of this, her office at Skadden was full of red shoe tchotchkes – from tape dispensers to door stops and paperweights – gifted to her over the years. One of her favorites was the Champion of Justice Award she received from the Harry and Jeanette Weinberg Center for Elder Justice from the Hebrew Home in Riverdale. The award was fashioned out of an actual red shoe affixed to a wooden box. A good way to get on her good side was to wear red shoes, provided you wore them with stockings, always with stockings.
Judge Kaye also downplayed her status as “the first woman to” despite the many barriers she broke through, but she never minimized her femininity or her love for and pride in her family. She was absolutely in love with her grandchildren and let everyone know it. She took long vacations with her family before her time on the Court of Appeals. Family time was important and so was work. She made room for both. She often told me that while in private practice prior to her time on the court, when things got busy at work she and her husband would meet at home for dinner with the family and then return to the office.
Judge Kaye had the work ethic of an Olympic gold medalist. Her dedication to legal writing is legendary. She was an assiduous preparer who by all appearances was untouched by the urge to procrastinate. But for her, the practice of law in all its forms was not work; it was a labor of love. I think working at her big desk, bent over a draft of something, was one of her favorite places to be.
But it was the work she loved regardless of location. She could and did work anywhere. Once as she was preparing to attend and present at an international arbitration conference in Mauritius, I asked her what she planned to do on the flight. I was thinking about all the sleeping and binge-watching I would be catching up on if I found myself in her situation. In response she told me that she was looking forward to “curling up” on the 21-hour flight to review and comment on a draft chapter of “The Restatement of U.S. Law on International Arbitration.” Feeling deeply inadequate I did not ask her about her plan for the return flight.
Although she was a runner while she was on the court, she was mostly devoted to walking in her post-court “afterlife.” Exercise was her way to quiet her mind, ground her thoughts as she traipsed through New York City. Indeed, Judge Kaye walked to the Skadden offices from her apartment 30 blocks away nearly every day, in all kinds of scenarios, weather-related or otherwise. Not even a group of rowdy Santas traversing midtown bars during SantaCon could deter her. And she was an early bird. When it was still in operation, the clothing store Forever 21’s Times Square location used to be open by 7:30 a.m. and she would frequently stop in on her walk to work and pick something up.
Walking back and forth to her home on the Upper West Side also provided opportunities for her to be spontaneous and exercise her love of the arts by stopping by the theater district in Times Square or the Lincoln Center box office to catch an unplanned performance. She loved the opera and had subscription seats at the Metropolitan Opera House, and I am sure she walked to those performances as well.
Just as she took care of herself by exercising and patronizing the arts, Judge Kaye cared about others, especially the people in her orbit. For example, she knew the name of every single person who worked at Skadden. From rainmaking partner to cafeteria staff, she knew not just the name but some unique facts about that person, such as the names of all their kids and what the kids wanted for their birthday. The older (and more forgetful) I get, the more I am in awe of this skill. I can still see her coming off the elevator and announcing the names of the two receptionists sitting behind a set of glass doors. She would shout their names in greeting, over-enunciating the last syllable of their names – genuinely happy to see them – and stop and chat before continuing to her office.
She was generous with her time and with compliments. And this was not just a Skadden phenomenon. Whether attending the Annual Meeting of the New York State Bar Association, or Pomodoro, her home-away-from-home New York City neighborhood restaurant, or Lodge’s, a favorite store in downtown Albany, she received a hero’s welcome. Her kindness was not performative – it was truly felt and to the bone. Especially when it came to colleagues and coworkers. I never saw her get mad. I think she recognized when people tried their best and, in general, she did not waste time sweating the small stuff.
If there was one thing Judge Kaye did not consider to be small stuff, though, it was tardiness. She was always on time. Because lateness mattered to her, it mattered to me. She typically eschewed overscheduling, but there was a time when circumstances dictated that she attend an event at Hofstra University on Long Island in the morning and an important pitch in lower Manhattan in the afternoon. I volunteered to drive, thinking that would eliminate the uncertainty of multiple Ubers. The error of that line of thinking was apparent when, while en route from the morning meeting, I realized to my horror that I had put the wrong address into the GPS. I corrected the error, but when the GPS was finished recalculating the route, it looked like we would be late for the pitch. I floored the gas pedal. She looked at me and said, “Jennifer, I am going to be quiet now.” Miraculously, we pulled up to the location on time and just as the attendees were gathering to go inside. I believe that if I had made her late to that pitch it would have been just fine and she would not have held it against me. But I am grateful, to this day, that I did not have to test that belief.
In the years since she passed away, I continue to hang in. I am still practicing and still trying to follow all the advice she never spoke in words but imparted in deeds. Be prepared. Be kind. If you are lucky enough to love what you do and the people you do it for, do not give up. Work hard but enjoy the breaks if you can take them. Don’t skip the arts or exercise. Dress like you give a damn. I will never live up to the standard she set in knowing so many names, but I do make my best effort.
When it comes to long flights I refuse to change my binge-watching ways – even Judith S. Kaye could be wrong once in a while.
But she was 100% right about red shoes and wrap dresses.
Jennifer Smith, chair of NYSBA’s Law, Youth and Citizenship Committee, is a member of the New York and New Hampshire bars. Prior to her role as assistant city attorney in Portsmouth, N.H., she practiced in New York and worked in city and state government and the private sector. She is also a former chief financial officer and chief operating officer of a midsize firm.
