Aside from an unhealthy obsession with J.Crew a few years ago, I wouldn’t normally classify myself as preppy. Maybe a touch of gingham and a crisp button-up shirt here and there, but you probably won’t find me repping giant Tory Burch logos or Lily Pulitzer prints. I did, however, feel inspired to embrace my inner prep while traveling up the coast over the weekend. I packed this scalloped skirt in white and my very first pair of Jacks among other New England-inspired pieces. On the top of my wishlist: this leather and canvas tote (now 40% off!) and this floral print backpack (drool). Just the right combination of pretty and prep.