I offer this 1950 portrait of Peggy Guggenheim as part of my ongoing effort to trace the history of older fashion eccentrics. Guggenheim was 52 here, just barely meeting my arbitrary cut off for an older woman.
The sunglasses are the wildest thing about her outfit, but everything else is also unusual. The very wide collar on her dress (or perhaps a small cape) is adorned with large beads and embroidery. The wide, stiff necklace looks very fancy, too. And of course small dogs are the ultimate accessory.
Not one to give up a good thing, she remained fond of those glasses. This photo shows her still wearing them fifteen years later.