I notice that this discussion is almost 100% about East Coast colleges. Makes me thankful to be in CA. There are so many things about my State that make me crazy but the rather relaxed approach to status clothing is not one of them.
As for equestrian boots…I actually own several pair…no not the 1K version…but the over the counter version…at just several hundred $$$. Know what…they are the MOST comfortable shoes I own. I can walk for hours and hours over cobble stones, thru puddles, Pompeii and Ephesus are not a problem… they are comfortable working shoes. Just happen to not look like the should accompany a pair of Ben Davis pants.