Hilary Duff may be the most grounded former child actor around (I mean, look how her peers Lindsay Lohan and Amanda Bynes are doing right now), but she still lives in this Venn diagram of a bubble where "fame" and "white privilege" intersect. Sidenote: Remember when Julianne Hough did blackface for her Orange Is the New Black costume? BLACKFACE. IN 2013. Anyway, for Halloween this year, the ex-Lizzie McGuire star dressed up as a sexy pilgrim (which is already offensive enough as is), while her boyfriend Jason Walsh, a white man, committed a far greater crime by showing up as a Native American—headdress, face paint and all. Let me repeat: a white man in a Native American costume. This is never a good idea. Of course, Hilary Duff and her boo got properly dragged on social media, and the actress/singer took to Twitter to apologize: "I am SO sorry to people I offended with my costume. It was not properly thought through and I am truly, from the bottom of my [heart emoji] sorry." As long as we learned a lesson, Hil. —Kristen Yoonsoo Kim