The Boater (or Skimmer) is traditionally made of stiff sennit straw, with a flat crown and brim, plus a striped ribbon. It was considered an essential sign of summer in the late-19th to early-20th century. The Boater was favoured by Harrow School, by early FBI agents, gangsters, barbershop singers & Venetian gondoliers.
The Boater is sometimes avoided because of its connotations - school uniforms, upper class layabouts, barbershop singers, blackface minstrels and so on. Please set aside those connotations and give it a try! A Boater looks amazingly stylish and can be completely comfortable, as long as it is of the correct size and of high-quality construction, with a proper, 'floating' sweatband. If it's the wrong size or of low quality, then a Boater will quickly make you feel uncomfortable, overheated and miserable, so be warned!