Answer:

preppy

Answer	Crossword Clue
PREPPY	Ivy League aspirant
PREPPY	Like J.Crew clothing
PREPPY	Very Ivy-League

PREPPY	Neatly dressed person, maybe
PREPPY	Private school pupil
PREPPY	Like J.Crew clothes
PREPPY	One at Exeter
PREPPY	Groton student
PREPPY	Like Top-Siders and khakis
PREPPY	Ivy League-ish
PREPPY	Lacoste-wearing, maybe

PREPPY	Wearing a polo shirt and boat shoes, say
PREPPY	Like an Andover student, say
PREPPY	Private school-ish
PREPPY	Phillips Academy student
PREPPY	Like a Washington and Lee student
PREPPY	Polo wearer, perhaps
PREPPY	Like J.Crew wares
PREPPY	Like some boarding schools