Interesting. To me dresses or pencil skirts with jackets/ booties and menswear inspired are not (necessarily) opposite. Opposite to me might be...say....super bombshell flat-out-intended-to-be-provocative vs. extremely modest and covered up. Or extremely rugged and RATE vs. light, delicate, refined.
Okay- I guess those are extremes.
But in your example, Shannon, it feels to me like just liking a change of silhouette. The overall style direction can be quite similar. True, if you wear a dress with those pretty green retro pumps, that would feel much more feminine. But even then...your menswear inspired looks usually include ladylike touches, whether a clutch, some jewellery, or even just bright lips!