The man asked for versatility... dub monks have that. I suggested brown semi brogues, black whole cuts, brown dub monks, and then black semi brogues or black dub monks.
dub monks are a lot easier to wear with denim, and the vast majority of ppl in this forum would agree with me they are a good looking shoe. I guess if I were to slightly revise my advice, it would be in this order, by importance:
Brown semi brogues (Suit or jeans)
Black Wholecuts(suit or tux)
Black Semi brogues (honestly suit only, but there are ways to pull it off i guess with jeans)
Brown Dub monks (Suit or Jeans)
Black Dub monks(Suit or jeans)
a black straight up captoe also works only with a suit, and IMO there is never a time a straight black captoe can be worn when a black whole cut could not, but a whole cut can also be worn with a tuxedo.
You could also inserts full brogues where the dub monks are, or austerity brogues, which are apparently coming out on the olfe this fall from meermin. (i'll probably be buying all colors...) You will likely get even more versatility out of those, and if dub monks are coming off trend then the full brogues or austerity brogues will maintain their classicness, as they have never been out of style.
Also Hendrix good point, I like the give a man to fish/teach a man to fish reference