I agree with almost everything in this critique, but I think with pants so narrow at the leg opening you can't have any break. They definitely look like a sub 8" opening and once you get much smaller than that any break just makes them gather like you pointed out. Unfortunately, there isn't anything you can do for that jacket and it's obviously too shot. Not even trendy short, just too short. However, I am a fan of this classic colour combo and I definitely think you have defeated the security guard look and turned into something much more interesting.