Hoping to debut his shoe line at the 1982 Market Week in New York, Kenneth Cole didn’t have the money for a hotel room, never mind a showroom. That of course left one option – selling shoes out of the back of a truck.

But it wasn’t that easy for KC, the city shot down his request, only granting parking permits to utility and production companies.  In a clever twist, Cole changed the name of his company from Kenneth Cole Incorporated to Kenneth Cole Productions, and applied for a permit to shoot the feature film, “The Birth of a Shoe Company”. 

In two days he sold over 40,000 pairs of shoes outside the New York Hilton.

 Ralph Lauren dressed Diane Keaton like a man – Oscars were won

Shortly after marrying Ricky Low-Beer, Ralph Rueben Lifshitz (aka Ralph Lauren) bought the now-famous Polo logo from a business partner. By 1972, Lauren found success with his “Polo shirts” – outfitting the cast of the feature-film remake, The Great Gatsby.

But it wasn’t a little pony that elevated RL into the fashion spotlight – it was some old fashioned cross dressing. The 1977 Best Picture winner, Annie Hall featured an androgynous Diane Keaton decked out in Ralph Lauren duds. It would be an understatement to say that the wardrobe choice “worked”.

Today, you can buy Ralph Lauren paint. 

Vera Wang outfitted a woman that got her knees busted up by a guy named Gillooly

After failing to qualify for the 1968 Olympics, former-figure skater Vera Wang set her sights on fashion. Following a 15-year stint as a magazine editor, Wang opened a New York bridal boutique in 1990.

As a side job, Wang was contracted to outfit Nancy Kerrigan for the 1994 Olympic Games. One brutal attack later, the entire world knew who Nancy Kerrigan was, and subsequently, who Vera Wang was.

Wang has since made custom wedding gowns for Mariah Carey, Jennifer Lopez, and other A-list elite.

Jason Wu dressed up dolls, now he dresses up Michelle Obama

Jason Wu was a lanky design student that liked to dress up dolls. Of course, those who judged him are probably eating their hat. At the age of 17, Wu was named Creative Director of Integrity Toys. For seven years, Wu worked and saved, until he had enough to bankroll his own fashion label – which he debuted in 2006.

Wu attracted clients like Ivana Trump and January Jones – but in 2008, he hit the media jackpot. OBAMA. After fashioning Michelle Obama’s inaugural gown, the 26 year old Wu has cemented himself into the fashion culture.

If you can’t afford his clothing, you can always buy one of his dolls (the going rate on eBay is $275)!

Tory Burch unquestionably proved that it’s “who you know”

Tory Burch, a Manhattan socialite with a taste for fashion, launched her fashion label in 2004. Oprah liked it. Nuff said.