Bailey's heritage is linked to Old Hollywood glamour. Since Mr. George Bailey himself set up shop in Los Angeles in 1922, he has created hats for Men of Style such as Humphrey Bogart, Cary Grant and the Rat Pack.

While times have changed, we believe that the Bailey Man of Style is synonymous with being a gentleman.

For this Fall/Winter season, we asked six tastemakers from all walks of life to what it means to embody that 'gentlemanly' quality.

Dapper Lou, wearing the Draper III

"Style is always a work in progress, but nevertheless he works in confidence" Dapper Lou

A gentleman's style is not influenced by the world around him. But rather he creates his own principles not guided by popular demand. He must always connect with his sense of style. As his taste grows his style soon follows. Staying true to his inner person while humbly learning new things. A gentleman's style is an independent source of his livelihood. He is one who pulls the garments together and in some sense, pull them apart. Pablo Picasso once said, "Art is the elimination of the unnecessary." He tastefully looks through his wardrobe and creates a masterpiece. Style is always a work in progress, but nevertheless he works in confidence. A gentlemen consistently inspires and leaves a legacy without even realizing it.