Heels with socks are an unconventional trend so much so that Leandra Medine, above, might declare it a Man Repellant. First mention of socks and sandals and we are immediately brought back to the traumatic days of our dads leaving the house in said trend and trust us, it was 50 shades of embarrassing.That being said, we love the chance to extend the life of our favorite sandals, open-toes, and absence of tights past the warmer seasons. Since it is not the easiest trend to conquer, we've gathered 11 street style shots for inspiration on how to correctly rock socks with heels. Whether you want ankle socks that give off the girly vibe of our days on the playground or knee-highs that are a tad more sexy, here's how to do it.