Avira > for a man to marry a wan from a less well-to-do background.
oi vei. To the intended point: girls would exchange dresses by Tu B’Av, but to a degree – king’s daughter with Kohen Gadol’s … same here – “less well to do” … So, a guy with 10 shoe stores should marry someone with 2 shoe stores.
Now, you can ask – if every man marries “less well to do”, what is gonna happen with smartest/richest girls and poorest boys?! A possible answer is – this advise is addressed to the top layer of Talmidei Chachamim (who learn this Gemora). Now, it is a biological fact that male species have more variability than female. Ie. there are more super-smart men and super-stupid men, super-angry and super-calm … [you may find this observation to explain a lot of things in life …] So, the top level of T’Ch need to go a little lower, but a below-average men will probably get wives that are smarter than them. May be a punishment to both.