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8 results for PREPPY from Modern Era puzzles:

Date	Grid	Clue	Author	Editor
Wed Dec 10, 2025	31A	Like some boarding school attire	Kareem Ayas	Shortz
Sat Apr 26, 2025	42A	"Gossip Girl" fashion descriptor	Sarah Sinclair and Rafael Musa	Shortz
Sat Apr 22, 2017	24A	Like an ascot, perhaps	Adam Fromm	Shortz
Tue Dec 6, 2016	29D	Like some boarding schools	Ed Sessa	Shortz
Fri Apr 3, 2015	12D	Wearing a polo shirt and boat shoes, say	Patrick Berry	Shortz
Fri Aug 18, 2006	10D	Lacoste-wearing, maybe	Joe DiPietro	Shortz
Mon Sep 5, 2005	50D	Ivy League-ish	Lynn Lempel	Shortz
Sun Feb 4, 2001	93D	Like Top-Siders and khakis	Frank A. Longo	Shortz

1 result for PREPPY from pre-Shortz puzzles:

Date	Grid	Clue	Author	Editor
Sun Apr 10, 1988	119D	Groton student	William Canine	Maleska

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