Pull everything out. Sort into bins: "Keep," "Sell (Depop)," "Trade (friend)." You need 20% statement pieces and 80% basics.
It is about storytelling. The oversized blazer tells the story of the business major. The paint-stained carpenter pants tell the story of the art student. The chunky platform boot tells the story of the girl who has to walk across a massive campus in the rain and refuses to ruin her hemline.
Pinterest is your creative director. Search terms: "Dark academia winter," "Miami preppy summer," "Corporate goth." Pin for one hour. Notice the common denominators.