PREPPY
| Date | Clue |
|---|---|
| 2025-12-10 | Like some boarding school attire |
| 2025-04-26 | "Gossip Girl" fashion descriptor |
| 2017-04-22 | Like an ascot, perhaps |
| 2016-12-06 | Like some boarding schools |
| 2015-04-03 | Wearing a polo shirt and boat shoes, say |
| 2006-08-18 | Lacoste-wearing, maybe |
| 2005-09-05 | Ivy League-ish |
| 2001-02-04 | Like Top-Siders and khakis |