Elitist, conformist, materialistic and competitive. That is how Westporters are often described, at least in books and movies they are.
“The Man in the Grey Flannel Suit” is a book, and later movie, written by Norwalk native Sloan Wilson and published in 1955. The book follows Tom Rath, a World War II veteran currently working the corporate world and feeling the pressure to earn more money for his financially unstable family while yearning for his freedom in the military. Unsurprisingly, a story about a man feeling pressure to work a job he doesn’t enjoy for the sake of money is set in Westport.
Westport is highly ranked for wealthiest towns in the state along with neighboring towns like New Canaan, Darien, Greenwich and Weston. Staples is first for best Connecticut public schools according to Niche and sixth for best schools overall in the state according to U.S. News, and my experience as a Staples student reflects that.
Although fictional, stories like “The Man in the Grey Flannel Suit” scarily mirror my own experience at Staples where it feels like no one is enough of an overachiever and going to an impressive, expensive and prestigious school is all that matters to some students.
Although I think Wilson’s caricature of Westporters has held true over the past 70 years, I don’t think other pieces of media have been so spot on.
With the recent popularity of “American Housewife,” a tv show about mother Katie Otto, her husband and three kids living among upper class neighbors, friends and parents in Westport, I’ve watched a handful of clips on TikTok . The show tried to be comical in its portrayal of Westporters, creating characters that have so much money to the point they’re out of touch like Cooper, the best friend of Katie’s son. Katie also gets involved in competitive rivalries with other Westport parents who are usually health obsessed, extremely wealthy, passive aggressive and judgmental.
Rather than pointing out any real consequences of Westport work and school culture, it falls on typically “spoiled, rich New Englander” stereotypes to make the Otto family more relatable. I’ve lived in three different states and four different towns, including another town in Fairfield County, and Westport has by far the friendliest, smartest and most fun people to spend time with compared to any other school I’ve been in.
I do think the media about Westport has made some good rather than just pointing out the bad. In 1947, the movie “Gentleman’s Agreement” starring old Hollywood stars Gregory Peck and Dorothy McGuire was released, and was inspired by Laura Zametkin Hobson’s novel of the same name. The movie follows Peck’s character, Philip Schuyler Green, who is a journalist pretending to be Jewish to expose widespread anti-Semitism in New York City and the neighboring towns of Westport, Darien and New Canaan. Unlike New Canaan and Darien, Westport was one of a few towns in Fairfield County that was more inclusive to Jewish families, creating one of the strong Jewish communities in the area to this day.
The success of the movie also brought many people to Westport, helping establish it as a cultural center for the arts. Movie stars and famous figures like Paul Newman, Anne Hathaway, F. Scott Fitzgerald, Martha Stewart and Shonda Rhimes have all either lived in or currently reside in Westport.
While some interpretations of our town aren’t entirely positive or accurate , I do believe that it is important to recognize where media representation of Westport is right. Art mimics life, so when films and books set in Westport point out issues many Staples students and Westporters face, perhaps we should pay attention.
