Jimmy Kimmel Roasts Martha Stewart's Homeless Halloween Costume: "This Is How You Know Your Assistant Hates You"

Martha Stewart’s Halloween costume is the talk of the week, and not in the way she hoped. The lifestyle mogul dressed as a homeless person, complete with a cardboard sign and dirt on her face, and posted the since-deleted photo to social media. Jimmy Kimmel caught wind of it and spent part of his Monday monologue mocking the ensemble, calling it ridiculous and joking that the costume proves her assistant hates her.

Stewart initially defended the look as a way to raise awareness about homelessness, but the explanation didn’t land. She later apologized on Instagram, admitting the costume was insensitive and simply not funny. That could have been the end of it, except she followed the apology with a post about free pastries from a Brooklyn bakery, which sparked a whole new round of criticism about the optics.

The whole saga has people debating celebrity costume controversies, tone-deaf social media moments, and how awareness campaigns can go sideways fast. So we want to hear from you: what’s the most tone-deaf costume you’ve ever seen, celebrity or otherwise? Sound off in the comments.