I think I might be having a 'mid life' crisis as I have many of the items mentioned! My first gilet bought to beef up my not warm enough winter coat- gets far more use than originally intended ( its really useful in the house when its chilly). I like stripy tops, wear leopard print trainers, and 'sensible shoes' . I own a fleece pullover ( well I've had a fleece of some sort since they were first invented- although I no longer use them just for keeping warm half way up a mountain ). I rarely wear makeup. -No hope for me then!
I think we all mostly dress to suite our shape, colouring, life style and yes to some extent our age.
I have recently mostly retired so am still finding my feet in the smart casual world- any hints gratefully received!