Since that time, Lebowitz has worked on various book projects that have not been completed. This includes Exterior Signs of Wealth, a long-overdue, unfinished novel, purportedly about rich people who want to be artists and artists who want to be rich. Her book Progress was first excerpted in Vanity Fair in 2004, but has yet to be completed as of 2023. When discussing her writer's block, she said: "My editor—who, whenever I introduce him as my editor, always says, 'easiest job in town'—he says that the paralysis I have about writing is caused by an excessive reverence for the written word, and I think that's probably true." Due to her writer's block, Lebowitz has largely supported herself with television appearances and speaking engagements. She has said, "It's what I wanted my entire life. People asking me my opinion, and people not allowed to interrupt." She tours as a public speaker, represented by the Steven Barclay Agency. In addition, she has made several appearances on Late Night with David Letterman and had a recurring role as Judge Janice Goldberg on the television drama Law & Order from 2001 to 2007. She does still write journalistic pieces; Lebowitz has been employed as a contributing editor and occasional columnist for Vanity Fair since 1997. Through her public appearances, Lebowitz has reached a wider audience who have come to know her trademark style. She is known for her clever quips and observational humor on a range of topics, including New York City, gentrification, art, literature, and politics. She typically wears men's suit jackets (made bespoke by the Savile Row firm of Anderson & Sheppard), white shirts, cowboy boots, Levi's jeans, and tortoiseshell glasses. She often speaks of her treasured pearl-grey 1979 Checker cab, the only car she has ever owned, which she describes as "the only monogamous relationship I've ever had in my life". In September 2007, Lebowitz was named one of the year's most stylish women in Vanity Fair's 68th Annual International Best-Dressed List. She is also known for her massive book collection, 10,000 volumes in all, including at least one shelf of soap-carving books, and her refusal to use many technologies, including cell phones and computers. A heavy smoker, Lebowitz is an advocate for smokers' rights. On Late Night with David Letterman, she once stated, "This is what 'public' means," referring to annoying people around you with your behaviour. She has not