Above: I am infatuated with this atmospheric shot of Inception's Joseph Gordon-Levitt and Ellen Page. In it, the cutesy Page looks much more sartorially credible in ankle grazing peg-legs, demure heels and tux jacket and bow-tie.
Above here, the full-lipped and luscious Sofia Coppola is dressed in a pleated shirt which directs the look away from looking too austere.
Personally, I would shy away from the whole hog approach as styled by COS (above) but this high street shop is always a good bet for manly accessories if you just want to dip your toe in. Every season they seem to stock a detached white cotton collar here, a leather tie, a bib there... and as long as you wear it with something feminine, a kitten heel (as on Page) a bit of feminine texture (Coppola) or maybe a padded shoulder or fitted jacket, you'll stay the safe side of the Modernist muse without being accused of dabbling in all-out transvestism.