I have worn these shoes... once? Twice, maybe?
Well, Ms. D. This is a doozy. My initial thought was "Toughen it up with jeans" and then you were all "NO JEANS!" so I was worried. BUT fear not, I think I've figured it out.
See, the shoes are unabashedly feminine, so there's no point in fighting it. The strategy is to toughen them up by over-the-top woman-ing it up. I would pair them with a sheer maxi skirt like the ones at American Apparel (get some boyshorts or a mini-skirt to wear under it), and maybe a worn-out wooly little sweater or tee. Ideally I would top it all off with a leather jacket, but a denim jacket or army green canvas jacket could just as easily do the trick. Then pile on the jewelry man, big pearls...maybe even a huge gold medallion! Basically toughen it up by over-the-top woman-ing it up. You know what I mean?
In that same vein you could toughen up the look by going for "tight and femme fatale vibes," which I know is totally your steez. Pairing a very tight pencil skirt in a bold leopard print, or maybe leather, with a cropped sweater (perhaps a couple sizes too big for maximum slouchy-ness and sexy off-the-shoulder effect) could also achieve great levels of bad ass-ery. If you're up for it maybe even rock some little ankle socks? Ok maybe not, but if you were feeling in a funky mood I'd highly recommend it.
I looooooove the heels + ankle socks thing- I've been trying to work that into more frequent rotation in my everyday life. Leopard print! Also: Holy balls this dress is shooooort. (Rodarte for Target, obvs.)
The grey socks with the shoes is SO best.
Do you have do you have something in your closet that you don't know how to wear? Email firstname.lastname@example.org.