Brilliant Thread Principessa!!
I love pill-box hats. The first one I remember seeing was the one Kate wore when arriving in New Zealand (I think, or Austrailia? Either way, that royal visit!). I remember thinking that she looked so professional and smart...and a little like a British post-box!
I think the pill-box is very understated and elegant, I love the pink one Mathilde wore, and Maxima has worn some beautiful ones too. I think they can be hard to pull off if the wrong size or if the hairstyle is wrong. For example Vic of Sweden wore a pill-box hat to Prince Nicholas' Christening, and I don't know if it was the size, the hairstyle (a bun) or the sitting of the hat but it just looked wrong to me? I think if I were to wear one I would wear my hair down with some loose curls (I have very long blonde hair!).