Since he joined sister Kelly at the helm of Hamilton in 2003, David Hamilton's goal has been to reach the next generation of Hamilton shoppers without compromising the company's roots. "At that time, the business was successful, but in terms of growth it was very steady," says David. "We've expanded our product line. We used to only make custom dress shirts and we now offer shirts in standard sizes and a contemporary line." The strategy has worked. Despite a brief dip following the financial crisis, trends have been moving up and to the right, meaning the fourth generation of the Hamilton family to embrace the shirting business will likely pass down a healthy brand to the fifth generation.