5 Combat Boots Outfits That Prove These Shoes Go With Everything ... options that will make your school girl outfit noteworthy. Once you've got your main preppy piece, such as a pleated skirt ...

you're about to be transformed to the Hamptons girl of your dreams ... is essential to Jack Rogers' shoes and is an instantly recognizable feature within preppy fashion. JSYK, Barbour is a ...

At first I thought, oh, that's a fluke, but it turns out that the preppy flat shoe is ... Kelly Rutherford from Gossip Girl - she looks like she'd wear boat shoes on a weekend.