Simply sign up to the Style myFT Digest -- delivered directly to your inbox. The pillbox hat, that demure little disc, has long been synonymous with a certain correctness bordering on prim. “I started ...

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 ...