This look was probably made most famous by Bridget Fonda in the movie "Singles." But I can actually remember the exact moment when I became aware of this fashion statement. It was 1993, and I was watching "Warlock 2: The Armageddon" in the movie theater, and I kept getting distracted from the plot (what little there was of it) by the heroine's outfit.
When will this signature look return?
Paula Marshall was clad in a lightweight floral print dress, paired with a big ol' pair of black military boots. The dress was the sort you might see Elaine Benes wearing in Seinfeld, albeit without the white pie collar. The boots belonged to either a construction worker or a punk rock singer. Together they made a pairing that was either inspired or horrifying, depending on the situation.
Chalk it up to the early fumblings of the new wave of "Girl Power" feminism. Women were feeling their way through a world where it was okay to wear lipstick if you wanted, and it was okay to wear combat boots if you wanted. And heck, maybe you wanted to wear both.