There is really no such thing as an out of style briefcase. Selecting the right one for you is all a matter of personal style and taste. If your personal style reflects a more classic look, you might find yourself more drawn to the vintage style briefcases that look like they would be carried by someone like Don Draper. And there is nothing wrong with looking like Don Draper- no matter what year that it is. The more modern designs that are made from softer materials and look like messenger bags are designed for the business person that likes to look modern and up to date- typically an early adopter when it comes to technology. No matter what your style- you will never look bad when carrying a briefcase.