Most wouldn't value a sharp fashion sense over a hard earned college degree, but in the cases of Anna Wintour and Tommy Hilfiger, not having a diploma under their perfectly accessorized belts was no hindrance to successes in life. It is common practice for employers to use diplomas a baseline yardstick to gage ability to succeed on the job, but these two fashion icons prove that one doesn't always need higher education in order to prosper, if you've got the drive and talent to succeed.

What Wintour and Hilfiger lacked in formal education, they made up for in passion and boldness, innovation and originality. Success doesn’t always come in tandem with a paper certificate, as many unemployed people with degrees may unfortunately attest to in today's economic climate.

Anna Wintour is infamous for her twenty plus year reign as the queen bee and Editor-in-Chief of Vogue. She dropped out of school at age 16, but she went on to build a fashionable empire on the pages of a magazine, where her word can make or break careers. On the job training and calculated ladder climbing delivered her to the top of her game.

Tommy Hilfiger also shot to fashion fame without any formal training as founder of his eponymous clothing line. Armed with the notion that he could design apparel better than current market leaders, he launched a collection that catapulted him to household name status, where his brand encompasses everything from clothing to bedding to perfume.

There has long existed the division between those who are street smart and those who are book smart -- perhaps we need to add a third category for fashion smarts to the fold.