Last fall I pulled leather and suede pants and skirts from several closets. They were put in the "save for a fashion rebound" pile, which ends up in a ben or trunk to be stored in never-land; attic or third floor closet, under Johnny's bed, above a bike rack in the garage... I'm sorry ladies, MyStylist says it's time to get them out again. I wouldn't have guessed so soon.
Field Specks:
• A straight black leather pencil skirt, with a kick pleat, opaque tights to match, "reasonable" platform heals (don't do boots, we're not going for dominatrix–well maybe, a little bit.) The length, is up-to-you. I like just past the knee, but mid-thigh on the right gal can look great. Check out the ones that mix knit and leather. Be extremely conscious of the fit.
• The black leather pants they're showing are really, really tight and skinny. Congrats to the .5% of the population that can wear them. Frankly in pants, I prefer a brown suede. Ralph Lauren does a beautiful tan bootcut pant. If that's too low a rise, consider this one in dark brown (the styling in this shot is unfortunate, however).
As for styling with leather. Let your story be mostly about the leather. I would go with very simple cashmere sweaters or silk tops. Lace could work, but be mindful of whether or not you are channeling Stevie Nicks (um, you don't want to). Above all, feel tough and a little sexy.