I don't get jodhpurs myself. They look costumey, like they ought to be worn with a pith helmet. And it seems like your trou would always be getting caught on the harnessing. Not my cuppa. Not a big fan of shoe ornamentation in general, though, oddly, I love a clunky full brogue.
I would think a Chelsea would seem at least as masculine to the average viewer as the monks that get such love on SF.