Photo of Nancy "Slim" Keith via On This Day in Fashion. Idea came thanks to a comment chain on Amid Privilege.

"In my day, different meant not having your hair done in a pompadour and adorning it with a snood, or not trying to hide your intelligence behind a sea of frills. I somehow knew there was a glut in that market. I opted for a scrubbed-clean, polished look. I thought it was more important to have an intelligence that showed, a humor that never failed, and a healthy interest in men." —Slim Keith in an excerpt from her memoir, Slim.

Queen Hill Equestrian Jacket ($575, currently sold out); Poet shirt ($250); Snake Belt ($195); vintage men's Rolex (prices vary); Chanel Rouge Allure Extrait de Gloss ($37); Tuxedo trousers ($30).