Christian Louboutin fringe boots, $1575
Oh, there was a time (LAST YEAR!) that I would have chosen the Thomas Wylde skull boots, but I've "matured" (ahem) since then. I think today I would choose--at the risk of looking like I'm out on bail--the grey pair with the silver cuff. With a very simple jersey dress (I would wear it in grey, too), a simple silver cuff bracelet and these boots, I do think a cool, edgy elegance would be achieved.