Intentional double entendre - prep being short for both preparation and preparatory school. As we gear up for the seasonal transition into autumn (or rather, as the weather here has for the most part decided to mimic autumn) warmer layers on top of summer clothes make the shift a bit easier to handle. But mostly I just like the New England prep style; it always reminds me of back to school shopping for obvious reasons. It made me so happy when I was in Maine and Massachusetts recently when I saw the occasional New Englander clad in dockers and polos, looking like they were on their way to the coast/vineyard.
Throw on some bright red lips (I just bought my first, YSL was the one recommended to me at Sephora but I chickened out and bought the $10 version at CVS) and dark nail polish, and you're good to go.
carven short cable sweater, la garconne; field maxidress, madewell; yves saint laurent rouge pur couture no. 1; super glasses ciccio, madewell; the leather transport tote, madewell; ropey soles espadrille sandals, madewell
image via polyvore