You could pick any of Madonna’s many incarnations out of a hat and chances are it would inspire your wardrobe, but there’s something about Madge’s late ’80s/early ’90s look that has us really psyched lately. Filmmaker Alek Keshishian followed her around on her Blonde Ambition Tour for his classic documentary, Truth or Dare, and the Madonna we see on screen is a woman at her most empowered. She’s healthy in her early 30s, a cemented star and dating Warren Beatty.
In between vocal exercises, mothering her flock of back-up dancers and evading the prudish censors in Canada, Madonna turns some simple, sexy looks—spaghetti-strap tank dresses, round sunglasses and her signature crucifix jewelry. Her wardrobe never overshadows her; her clothes are generally stark black, but Madonna is always in color. She seems relaxed and comfortable—just a dress and peroxide-blonde hair are all she needs to look good. We’ve picked some current day items that channel this moment.