Jimmy Kimmel tore into Martha Stewart’s controversial Halloween costume during his Monday monologue, ridiculing both the outfit and the explanation that followed. The “Jimmy Kimmel Live!” host focused on a photo Stewart later deleted from social media, as reported by Page Six.

“Martha Stewart, for whatever reason, dressed like a homeless person,” Kimmel told viewers. He added that he “love[s] seeing rich famous people get hammered for their costumes the day after.”

The lifestyle guru had portrayed an homeless person, putting dirt on her face and carrying a cardboard sign to complete the costume. After displaying the deleted image, the 58-year-old host turned the photograph into a joke about the economy.

Martha Stewart shared photo seemingly dressed up as a homeless person for Halloween.

She has since deleted the post. https://t.co/PzTX1BoDhK — Pop Base (@PopBase) November 1, 2026

“That’s how bad Trump’s economy is. Even Martha Stewart is homeless,” Kimmel joked. He then questioned how Stewart’s costume made it through planning, photography and publication without someone stopping it.

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“Now how does this happen? How does this woman wind up in that costume being photographed and posted? This is how you know your assistant hates you,” he said.

Kimmel did not stop with the costume itself. He also mocked Stewart’s initial defense, calling the explanation “strike two” in a Halloween controversy that had already generated criticism.

Stewart had told Page Six that the ensemble was intended to “bring more awareness to the very serious subject of homelessness.” Her response framed the costume as an attempt to highlight an issue she said she deeply cared about.

“Homelessness continues to remain one of America’s greatest challenges and ongoing crises, something that I care deeply about and I have spent a significant amount of time and effort supporting charities that combat this ongoing social epidemic,” Stewart said.

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Kimmel remained unconvinced by that reasoning and offered Stewart what he described as “a good general rule of thumb.” His advice was to keep Halloween costumes focused on the holiday rather than using them to promote awareness.

“Don’t use your Halloween costume to raise awareness of anything other than Halloween, especially when you complete the look with a boyfriend sweater from The Row,” he said.

Stewart ultimately issued an apology for the outfit after her earlier defense failed to settle the backlash. In a Sunday Instagram statement, she acknowledged that her first response had not adequately addressed why people found the costume offensive.

“It’s hard to admit when you’ve really screwed up. My earlier statement didn’t go far enough. I know many people are suffering economically. Wearing a costume like I did was insensitive and not funny,” Stewart wrote.

The apology did not end the attention surrounding Stewart’s social media activity. She continued posting after the costume scandal, and one of her latest uploads quickly sparked another round of criticism from followers.

On Monday, Stewart displayed a large assortment of free pastries she received from the new Altbau bakery in Brooklyn, New York. The post arrived soon after her apology and prompted followers to question the decision to showcase the food.

One follower asked Stewart to “deliver the bread to hungry people.” Another wrote, “PR team must be ripping out their hair .”

A third follower mocked the pastry post as “her version of ‘let them eat cake.'” The reaction added another uncomfortable chapter to Stewart’s Halloween debacle, even as she continued her regular social media activity following the apology.

Kimmel’s monologue centered on the disconnect between Stewart’s stated intention and the costume she selected. His jokes targeted the image, the approval process behind posting it and the awareness argument Stewart initially offered before acknowledging that the outfit was insensitive and not funny.