I absolutely love repping East Coast prepster chic sometimes, if not purely for the reason that it just feels like playing dress up to me because my normal style is just so.. not that. I'm from Southern California! And though, I've made some serious fashion decisions I regret (like that year I exclusively wore flip flops... yikes..), coming from a region with such a distinctive culture and style has a definite impact on your own distinctive style and tastes. Which I feel allows for a fresh take and perspective on other styles and do some real experementing. So here's my interpretation of what an Ivy League law student/lacrosse player wears to his first week of orientation... yeah, I know, it's specific. I'm still putting a collar on everything, because I think it's cute and the contrast with something as simple as an old sweatshirt really adds an air of sophistication to a look. Keeping it still slim and modern in a tightly constructed DKNY jean, paired with classic loafers makes for a perfect balance of modern and vintage.