Now & Then: Reese Witherspoon and Winona Ryder in Off-The-Shoulder Dresses Now & Then

Reese Witherspoon (wearing an Ulyana Sergeenko dress) at arrivals for SING Premiere at Toronto International Film Festival 2016, Princess of Wales Theatre, Toronto, ON September 11, 2016. Photo By: James Atoa/Everett Collection *** WELCOME HOME, ROXY CARMICHAEL, Winona Ryder, 1990, ©Paramount/courtesy Everett Collection