It wouldn’t be a fashion icon list without Carolyn Bessette-Kennedy. The wife of John F. Kennedy Jr. and former Calvin Klein publicist, Carolyn Bessette-Kennedy was considered American royalty for her girl-next-door looks and effortless personal. Defined by its minimalist charm, Bessette-Kennedy was a firm believer in investment dressing and not buying into trends—for her wedding, she disregarded the puffy silhouettes that were en vogue in the ’90s and opted for a slip silk dress.

Carolyn’s styles, from elegant workwear to weekend casual get-ups, are featured below.