The son of a German father and Spanish mother, Herold's interest in fashion started in high school.
The fashion-frustrated Herold joined the Pratt Institute in 1990 but left in 1992 for Marymount University's business school.
After he got his degree, Herold took jobs with Isaac Mizrahi as a production coordinator to learn the "ins and outs of the business.
After freelance gigs at Donna Karan and Ralph Lauren, doing both design and production work, Herold got a full scholarship at the Fashion Institute of Technology.
Going solo proved to be a good move, as the designer was awarded the 2001 "Rising Star" award by Fashion Group International.