I say this phrase a lot to describe a certain Thirtysomething-ish/late-80's-early-90's genre of style. Specifically my mom would always wear her long, thick hair in a braided bun (as a kindergarten teacher) and would have a little dash of blue eye shadow (as a chic, stylish lady). She most likely would be wearing a collared shirt, collared popped, of course, and when warm enough a pair of culottes. Yep.
When I went home for Christmas my mom and I went through her closet a bit and unearthed our favorite belts from back-in-the-day. Memories came flooding back of "my mom in the 80's" and I wanted to be listening to Neil Diamond and Peter, Paul and Mary while watching The Incredible Hulk in the apartment that the two of us shared circa '83-'87.