The drop-crotch pant can definitely be an intimidating style to wear at first. After all, worn incorrectly, they can make you look like a boy in the 1990's. However, they can look amazing (see Chloe Spring/Summer 2009 for proof!)
The Style Classicist:
Pair a pair of black drop-crotch pants with simple yet complimentary pieces like a drapey top, ballet flats, and Annie Hall sunglasses.
The Fashion Risk-Taker: