Diddy the Diddler is donning stripes in prison. Why did he pay off his Miami manse right before his bust? Later, get the scoop on celebrity spotting, including Palm Beach, Boca, and Miami: Lauren Sanchez’s lawsuit, Elle MacPherson’s real estate move, and her holistic journey. Nothing says “It’s fall, y’all,” more than a sparkling apple cider sangria. Our Bougie Bible picks include our fav Italian shoestore and the bougie’s tent at October Fest!

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