You can wear whatever shoes with whatever outfit you prefer, but most of the choices should be narrowed down to fit/style/color. And by fit, I do not mean how well fitted an article of clothing is; its largely unimportant.
Wholecut in terms of styling is more on the novelty end of the spectrum; too edge for business and not rugged enough for work/casualwear.
long wing bluchers, plain toe bluchers/chukkas, norweign split toes all work much better as the swiss army knife of shoe styling.
colorwise, black is formal, brown is less, light colors are casual.
so black chukka has a formal color, novelty design. doesn't bodes well for most outfits.