Looking cool over forty, fifty and beyond is not the easiest thing in the world. Cool is usually associated with youth and trying to look young when you’re not can easily backfire. There’s nothing sadder than seeing a mature woman still dressing as the ingénue she no doubt once was. That’s not to say I espouse dressing like Barbara Bush. Looks eventually fade but character and personality (insert wine metaphor here) get better with age. The same could be said for personal style. I think the older we get the more important it is to evolve our own personal style, curating from the wide range of tools that fashion provides us with four times a year. Be current but on your own terms. A great example of this is the Italian women Ana Gimeno Brugada. I always look forward to the street style photos of her during Milan Fashion week. Inevitably she has on the coolest accessories and has a penchant for masculine mixes that on her look totally natural. That’s the key, she knows herself so well that what looks daring and unlikely to others is perfectly suited to her. She’s clearly comfortable in her own skin and dresses to please herself, not to impress, and that is ultimately very cool.