Olukai Kaona Boot - Women's - $107.98

When you make your debut wearing the Olukai Women's Kaona Boot, your friends might wonder if you have a new sugar daddy or suspect that you're involved in some sort of black-market fashion trafficking. It's understandable; the water-resistant silky suede upper, soft woven cotton lining, and waxed full-grain leather details would fool anyone into thinking you dropped a paycheck on these puppies. - $107.98