As a youngster, Cesar Padilla, would intern fresh out of high school with Los Angeles pioneer punk rock record label, Frontier Records. He would then intern for the music and fashion departments of LA WEEKLY and began writing music reviews. Next, Cesar would then intern at International Alternative music distributor, Rought Trade.

Cherry, a vintage boutique, was started by Cesar Padilla and his creative partner Radford Brown, in 1997, in the Lower East Side of New York City. Cherry has since been featured in the top 10 of vintage in the world by publications such as the New York Times, Vogue, Harper's Bazaar, Elle, and many more. Cherry would also be asked to open two freestanding boutiques in the Virgin Megastores Flagships in Times Square and Hollywood. Cherry would close all freestanding boutiques in 2008 and go private as an archive for film, TV, music video, magazine, fashion design and other industries.

When Sotheby's went online with their fashion auctions and closed the in-house fashion department, Cesar and Radford were asked to run the online fashion department for Sotheby's.com working on Marilyn Monroe, Barbara Hutton, and Cher's auctions, and has even turned down Barbra Streisand. This lasted for three years. Cesar has also sat on the International Fashion Council's annual symposium next to fashion mavericks as Zandra Rhodes and Kenneth Jay Lane.