I have always considered myself aggressively anti-hat. Not in a dramatic way—just in a this is not for me way. I’ve spent years telling myself my head is too big, my face too round, my proportions too ...

I’m looking in the mirror at milliner Jess Collett’s studio in Notting Hill, London, where she’s just placed a petrol-blue pillbox hat on my head, adorned with a navy bow made from her grandmother’s ...