Hi Chris--just my .02 about what worked for me last year. Most of my outfits have a classic vibe and are neither very girly nor masculine.
I wore my Converse Jack Purcells all winter (Seattle) with cropped and ankle length skinnies and rolled/cropped boyfriend jeans--white, dark gray, and blue washes. I'd wear them with full length straight-legged jeans, too, if I owned any To my mind, a black blazer was an easy topper. Or a pull-over sweater either half-tucked or untucked. I wore only no-show socks with mine. When it turned to late spring/summer, I started reaching for the white sneakers. I hope that black will appeal more again come fall/winter. I think there is a "stumpifying" effect with a cropped pant + a higher vamp shoe--it's something I should watch out for as I'm 5'4" and not as slim as I'd like--but I guess I rated most of the combinations JFE or better.
Since last winter, I've purchased a black t-shirt dress that I think would work with the shoes, and I'd top that with an open cardi, if necessary. I think a soft sweater or scarf would be more than enough to soften-up an outfit and give it a feminine edge (should you desire that).