Charleston, South Carolina
Located on the Atlantic coast of South Carolina, Charleston is a prep's dream city. Sunny, warm, quaint, and fun, Charleston is ideal for laying out on the beach, sailing on the Atlantic, and shopping. The streets of Charleston are packed with all different preppy stores that showcase all the different preppy brands of fashion.
Washington DC
Our nation's political capital could also be considered our nation's preppy capital. DC is home to many young and energized future politicians who spend their days wearing business suits, but often bring out their casual preppy side on the weekends. I guess JFK left his preppy influence on this city for others to follow in his footsteps and liven up the nation's capital!
Boston, Massachusetts
The New England region is famous for its preppiness, and Boston is in the heart of it all. Home to sailboats, boat shoes, and prep schools, Boston showcases all that the preppy world has to offer. Boston and the surrounding areas of the Massachusetts Bay were a favored destination of JFK, who was by far our preppiest president.
Lexington, Kentucky
Home of horseracing, bourbon, and an SEC college, Lexington has grown into a well-developed southern city. The world-renowned Keeneland horse track is prep central, filled with people dressed in their seersucker suits and colorful bow ties. The fun college town is filled with students who are crazy about their cats and their preppy brands. The Greek life at the University of Kentucky is very prominent to the university, and it can be seen everywhere across the town.
San Francisco, California
When people think preppy and classy places, their minds don't really think about San Francisco. However, according to the Nantucket Brand, San Francisco actually has the most prep schools, yacht clubs, and preppy clothing stores per capita than any other city in the United States. Preppy guys love their boats, and the San Francisco Bay is a boaters paradise.
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