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This story originally appeared in the Jackson Free Press. It was added to the Mississippi Free Press website in 2025.
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We’re getting an amusingly large number of questions about the “theme” for this year’s Best of Jackson party, and how to dress for it; “monopoly” is confusing folks. So here it is: As always, you can dress however you want. Truly. (Ask Josh Hailey, and the people who gawk at him ever year.) But to be in the spirit, think “tycoon chic” or better yet, “bailout chic.” Ask yourself: If I were a CEO who just asked for bajillions of dollars (or his spouse) to bail out my sorry ass, how would I do it up at our last big shindig? Would I be classy? Nouveau riche? Truly tacky? Dressed in thrift-store clothes? A fur you have to pawn the next day? Or, just dress like a cop or jailbird. Or a shoe. Or a race car.

(Just came from a walk-through at the Auditorium, folks; it is looking amazing. Can’t wait for everyone to see it!)

Previous Comments

Bump: important alert.


Great party, Donna! I had an awesome time. :o)


I wanted to come but I wasn’t feeling very well. Plus, I had company over, so I couldn’t get away from them.

Founding Editor Donna Ladd is a writer, journalist and editor from Philadelphia, Miss., a graduate of Mississippi State University and later the Columbia Graduate School of Journalism, where she was an alumni award recipient in 2021. She writes about racism/whiteness, poverty, gender, violence, journalism and the criminal justice system. She contributes long-form features and essays to The Guardian when she has time, and was the co-founder and editor-in-chief of the Jackson Free Press. She co-founded the statewide nonprofit Mississippi Free Press with Kimberly Griffin in March 2020, and the Mississippi Business Journal named her one of the state's top CEOs in 2024. Read more at donnaladd.com, follow her on Twitter and Instagram at @donnerkay and email her at donna@mississippifreepress.org.