Yes, my understanding is the Holy Cross is rather preppy. However, I always leave such judgments to the students themselves. One person’s preppy is sometimes another person’s irony. FWIW, Bob Weir of the Grateful Dead used to wear Izod polo shirts when performing in concert. Not sure whether he counted as preppy or not.
Personally, I have never visited Holy Cross. So, all I know is via the internet.
Ohio University-Athens was kind of buried in my previous post, but I am very serious about it. Take a look at their Honors Tutorial College. You probably would get a full tuition scholarship, and I think you would fit in. OU is less peppy than OSU, and OSU has very few preps. OU is the hippest state university in Ohio, where I live.
https://www.ohio.edu/honors/future-students/programs/classics.cfm
https://www.ohio.edu/honors/future-students/index.cfm