Before landing at True Religion, Jeanann Williams worked her magic on brands like Alexander Wang and Victoria’s Secret while at powerhouse agency KCD. With her laid-back style and effortless approach to motherhood, Williams embodies the understated charm inherent in the east end town she calls home. Beach chic meets cool sophistication at the Montauk house she shares with photographer Ben Watts. The couple has passed their easy-going sensibility onto their daughter; already a world-traveler, Ruby’s eclectic wardrobe reflects her globetrotting upbringing—France, Ibiza, and Australia all before her second birthday.

Ruby, two, July 2011