I don't either. The best I can figure is it was mocking white boys. So what? Can't anybody take a little kidding?
I agree. And when I say I don't get it, I really, really don't get it. I admit I am completely out of touch on college fashion, but those pictures don't look "racial" in any way, black or white. And they don't at all look like it is trying to be insulting. They look like a modelling job for Sears or something. I don't see anything offensive here at all.
Preppy comes and preppy goes as far as being stylish outside of prep school circles, but it never goes away inside them. It’s a studied, affected, outdoorsy casualness wearing high quality fabrics made into conservative basic clothing. What appear to be very minor details make all the difference in the world to actual preps, it’s got to be authentic.
That said, I’ve worn similar in the early eighties. Still have the LL Bean duck shoes, those things are great. Indestructible and still waterproof after all that time. Wearing a collegiate pullover on top of an untucked button-down dress shirt is more recent, but you see that all over the place even with blazers in some cities. The print on the duck cloth pants is a little different, but I know from working with a few southern purveyors of preppy style that prints are a big deal so she’s probably got it down pat.
Looks better in that than her usual getup from what I can see, whether she intended to mock or not.