What happened to the Martha Stewart audiences once admired?
The witty, perceptive and effortlessly glamorous personality who could laugh at herself now seems overshadowed by a version of Stewart critics describe as irritable, self-important and increasingly difficult to warm to.
Her latest Halloween controversy has only deepened the impression that the lifestyle entrepreneur has become disconnected from the audience that helped build her remarkable career.
On Saturday, the 85-year-old lifestyle icon, whose fortune is estimated at $400 million, shared a costume portraying a homeless person. She wore ripped clothes, covered her face in dirt and held a sign that said, “I AM HUNGRY HELP ME!!”
The image appeared beside an advertisement for her home goods business, accompanied by the caption: “My QVC candles are perfect for Halloween!!!!!”
After the post sparked swift backlash online, it was removed. Stewart initially attempted to explain the costume as an effort to draw attention to homelessness, a defense that many found unconvincing.
With the criticism continuing, she offered a second apology and conceded that her first statement “didn’t go far enough.” She also acknowledged that the costume was “insensitive and not funny.”
Apologies aside, people make mistakes. Yet coming from a woman whose brand has long been built on impeccable taste and carefully considered presentation, the incident feels especially jarring—even to some people who know her well.
“The issue isn’t that people failed to understand the joke,” said a source who worked with Stewart for seven years and remains on friendly terms with her. “The issue is that there was no funny joke in the first place.”
I encountered Stewart years ago, after being invited to her Chelsea office to discuss a potential position. At the time, I handled media relations for designer Kate Spade, and Stewart had apparently taken notice of my work.
About 15 minutes before the meeting, her driver phoned to say she was on her way. The office seemed to enter full emergency mode. It felt like a scene from The Devil Wears Prada, with Miranda Priestly about to arrive.
I found the spectacle hilarious—and Stewart did too. That was part of her appeal. She was eccentric, commanding and larger than life, but her employees appeared to genuinely adore her. Crucially, she understood the performance and was willing to laugh along with it.
“The Martha of that era could certainly be intimidating, but there was always a spark in her expression,” the insider said. “She knew she was a character and seemed to enjoy inhabiting that role. Now the spark appears to be gone. What remains is the forcefulness without the warmth.”
Of course, Stewart’s seemingly effortless lifestyle was always the result of extraordinary discipline. It takes exceptional intelligence, determination and stamina to rise from a working-class childhood, start a catering company at home and transform it into an international media empire.
Stewart has always been formidable. But that confidence and toughness have also led her into serious trouble.
In 2004, she was convicted of conspiracy, obstruction and making false statements to investigators in connection with the sale of stock in a biopharmaceutical company and an alleged insider trading scheme.
“I’ll be back. I will be back,” Stewart declared outside the courthouse after she was sentenced. “I’m used to all kinds of hard work, as you know, and I’m not afraid. I’m not afraid whatsoever.”
She ultimately spent five months in prison, followed by five months of home confinement and two years of supervised probation. Stewart later settled the civil insider trading case and paid a fine.
When she left the Federal Prison Camp in Alderson, West Virginia, in 2005, she was wearing a handmade yarn poncho created for her by another inmate.
It was, in its own unmistakable way, a final flourish aimed at the Securities and Exchange Commission.
Where is that sense of humor today?
The Halloween faux-pas didn’t happen in isolation.
In August, Stewart seemed to fire a crumpet across the bow of the Duchess of Sussex.
‘If you’re an actress, it’s hard to then transition to a princess and then from a princess into a homemaking guru on a television show,’ Stewart told People magazine about Meghan Markle’s foray into the lifestyle genre. ‘It doesn’t sort of follow. So go from there.’
Perhaps the perceived slight was unintentional. Even so, is that an excuse?
Then there have been the increasingly thirsty photographs that she has posted to social media. Posing in a bathroom mirror in her lacy pajamas – decolletage bared. Pouting in the pool, by the bar, in the make-up chair. In Sports Illustrated’s swimsuit edition.
Let me be clear: I have absolutely no problem with women looking sexy at 25, 55 or 85. No one should be told to cover up because of a birthday, but there’s a difference between confidence and what seem to be attention-seeking behaviors that are beneath a diva of her magnitude.
It would be tragic for her to become a caricature.
On Saturday, the 85-year-old lifestyle mogul, worth an estimated $400 million, dressed up as a homeless person
‘Nobody begrudges Martha wanting to look hot, she never had to work this hard to get noticed. She was fascinating without trying,’ an event source who has hosted Stewart several times told me.
Her repeat appearances across season 16 of The Real Housewives of New York raise similar questions. The woman who once defined effortless sophistication now seems increasingly determined to chase every opportunity to stay in the spotlight.
A 2024 Netflix documentary aired her claims about her ex-husband Andy Stewart’s alleged infidelity – and her own extra-marital diversions.
‘I don’t know how many different girlfriends he had… but I think there were quite a few… If you’re married and you think you’re happily married, and your husband starts to cheat on you, he’s a piece of sh*t. Look at him as a piece of sh*t and get out of it, get out of that marriage,’ she said.
In a 2024 statement, Andy Stewart’s current wife (he and Martha divorced in 1990 and reportedly haven’t spoken since) said he had a ‘dark’ chapter of his life and called his marriage to Martha Stewart, ‘painful and abusive.’
Off camera, the interviewer reminded Martha Stewart that she also had an affair, early in her marriage.
‘I had a very brief affair with a very attractive Irishman, and it was just nothing,’ she said. ‘It was nothing… I would have never broken up a marriage for it. It was nothing.’
Look, Martha Stewart was never going to be a sweet older lady. She was never a sweet younger lady. But the saddest thing about watching an icon age isn’t watching them get older, it’s watching them lose the very qualities that made them iconic.
You used to be in on the joke, Martha.
These days, you’re beginning to look like the punchline.
