This article shook loose a few ideas for me. I have had several style changes in life, many imposed (or nearly so) by choice of school and career and geography/culture. When I find myself thinking about going back to what I liked 30-odd years ago, I have to be a bit more careful with implementation. We can't all be Vivienne Westwood on Carnaby Street, especially at almost 48, unless we really are Vivienne, still going strong in her 70s. But I still like zippers and black and white prints, and find myself going back to them, with current twists. I also admire pink spiky hair, but that's not happening on me (again).
O'Rourke is young (to me) and I think perhaps taken with the idea of a mature presentation. When I was first starting as a lawyer in the mid 1990s I really liked the idea of presenting as powerful and serious. For example. I had a Liz Claiborne red skirt suit that all the paralegals knew was my "court suit," so it was a definite totem for me.
I think that when you pass that 'mature' bump, you think less about what other people expect and more about what you like. And the 'mature' bump is not necessarily associated with any particular age, but comes more at a time of self assessment and acceptance.