20. Barack and Michelle Obama
Some argue that they're the most stylish couple to live in the White House since President Kennedy and First Lady Jackie Kennedy. Given their great personal styles, it would be hard to argue otherwise. Barack Obama has taught us how to wear suits again, as he often goes for clean lines and well-fitting jackets. Michelle is the mix-and-match master and frequents in high-end brands like Thakoon and Jason Wu, but still shops at places like J.Crew. These days, she's also known to make the career of an up and coming designer. The First Lady is doing it, doing it, and doing it well.