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.
This outfit was the stylistic equivalent of a mullet. Business on the top; rockin' at the feet. The dress had to be demure, and it had to be floral print. I remember seeing women trying this look in dresses that were striped or polka dotted, but it just didn't work.
The floral print dress had carried forward from the Laura Ashley trend that was so huge in the '80s. Laura Ashley prints morphed into boho/shabby chic in the '90s. And on the other hand you have combat boots and Doc Martens, which started with the new wave/punk scene of the '80s and carried forward to the grunge scene of the '90s.
But why people saw fit to "cross the streams," I couldn't say. But I am embarrassed to admit, I did it too. In my case, it was an attempt to game the system of the extremely restrictive dress code at my workplace of the time. I thought it was a cheeky look, like Tank Girl meets the Spice Girls. In hindsight, it was simply regrettable.
One thing I will say for this look, though: it was extremely comfortable. The floral print dress is always loosely fitted, which hides a multitude of body issues. And the boots are great for walking, standing, and dealing with inclement weather. I wouldn't go so far as to say it's a practical style, but I wouldn't be surprised if it came back some day.