I love these bright red pants from J.McLaughlin, they're fun, preppy, and bold! The "preppy" look is normally a lot of earth tones with small amounts of red (usually crimson) to "pop" your outfit, but I say stand out on campus. Clearly, to get into a preppy school like Harvard, you had to stand in the first place, so why not keep it going? This outfit also perfectly transitions to a cute holiday look, with a Nantucket vibe.
Beacon Hill is gorgeous to just walk around: famous cobblestone, beautiful homes, cute boutiques, and you meet some of the most interesting people. No lie, wish I got a picture of it, I saw a mom pushing a stroller in high heel Stuart Weitzman boots, going up hill, sporting a gorgeous fascinator. She became my goal in life.
So if you're looking for a fun day in Boston, just stroll around Beacon Hill and look up Acorn St. and my favorite, The Scarlet O'Hara House
P.S. Yes, I'm well aware I still have my fake tattoo on my wrist and my colored hair..... Argile and Plaid Life.