What are the semiotics of a sweater set? Do women have the right to bare arms? Are yoga pants okay for campaigning in a grocery store? How about the jumper? Women’s outfits have been scrutinized since the French heels of the first women in Congress to Hillary Clinton’s pantsuits and Michelle Obama’s sheath dresses.

New York Times chief fashion critic Vanessa Friedman talks with former Congresswoman Cheri Bustos, Chicago-based fashion designer Maria Pinto and Emmy award-winning costume designer Tom Broecker about women, fashion and politics over generations.