A pair of loafers, such as either top siders (a New England classic!) or basic leather loafers, and classic booties!
I felt super-chic in my handy trench coat, which gave me the comfort of a windbreaker, while helping me stand out from the tourist crowds!
I suppose wearing a scarf in New England in the Fall kind of goes without saying?
Americans are far more casual than Europeans, as you likely know, especially on vacation. Even in a big city like Boston, you'll fit in jeans, even at dinner.
I am all about the
sweater-and-shorts combo when I can rock it, and occasionally in late summer/early Fall in New England, I can get away with it!
I'm all about Longchamp on vacations, so that's what I would recommend for this type of
trip - looks nice during the day, but it's lightweight and zips, so your stuff is nice and safe in there.