A Real Pill

Along with other iconic Sixties fashions (baby-doll dresses, Peter Pan collars), pillbox hats have been one of my most hated clothing items. I hated everything about this hat style: the straight up-and-down sides, the flat crown, the sometimes bulbous shapes, the stiffness, the way it traditionally sat straight on the head; even the name is unappealing … I could not name a single redeeming feature, and I certainly never imagined I would ever not only own one, but wear it with pleasure.

Then along came this natural straw hat by Mr Individual of Melbourne, which is trimmed with caramel coloured braid and a jaunty, angled bow. I found it in a Salvos op shop (thrift store) and picked it up – in spite of the fact it was clearly a dreaded pillbox – because of the bow, the fineness of the straw, and because it looked in such pristine condition. At $25 it was not the cheapest hat I’ve ever bought in an op shop (never mind the price tag on new designer hats), but it was obviously a quality piece of millinery.

It looks more like an insouciant cap than a formal pillbox.

Luckily it fit well enough so that I could wear it on the back of my head, a more modern styling than the traditional straight on. It looks more like an insouciant cap than a formal pillbox.

Origin of an Icon

The precursor to the pillbox hat was military headgear. It was redesigned by milliners in the 1930s, and is in fact named after actual pillboxes that pills were once packaged in. It is of course most associated with Jackie Kennedy: a style icon in her own right, but this hat became synonymous with her look in the 1960s.

Jackie KennedyAudrey HepburnWhen Jackie was looking for a hat to wear to her husband’s presidential inauguration in January 1961, the American designer Halston decided with her to make a plain pillbox hat that would suit the style of her dress.

‘The simple but stylish hat caused a fashion sensation across the Western world, when many people watched the inauguration ceremony on television. The dent that Jackie accidentally put in the hat as she climbed out of the presidential limousine was interpreted as a special design feature, and the dented pillbox hat was immediately copied around the world.’ (The Century of Hats by Susie Hopkins, Chartwell Books, 1999).

The pillbox hat subsequently became Jackie’s trademark, and she wore them in fabrics and colours matching her outfit. Worth noting: she too usually wore these hats on the back of her head.

Glaser pillbox by Christian Dior, 1960Flamingo velvet pillbox 'Florentine' by Christian Dior, 1961At Tanith Rowan Designs there is an excellent article on the pillbox and how to wear it now in a modern way – this Australian milliner advocates wearing them tilted on an angle. That may not work with mine as it has such a deep crown, but even I am almost convinced!

Photos: October 2016