Whether you're looking for the perfect dress or the best beauty buys, shopping can be a gamble — and not just for you. Store owners also feel the pressure of choosing the right merchandise. To dig a little deeper, we went behind the cash register with six successful Chicago buyers to get the tricks of the trade they use to get you to spend your next paycheck. From the indie and mainstream finds at Sofia to the beauty product bonanza at Aaron's Apothecary, the method behind the buying madness lays ahead.
Photographed by Grace Willis